HOME

TheInfoList



OR:

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to
methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane ...
by replacement of one
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...
atom by an atom of
iodine Iodine is a chemical element with the Symbol (chemistry), symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , ...
. It is naturally emitted by
rice Rice is the seed of the grass species '' Oryza sativa'' (Asian rice) or less commonly ''Oryza glaberrima'' (African rice). The name wild rice is usually used for species of the genera '' Zizania'' and '' Porteresia'', both wild and domesticat ...
plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
as a source of
methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ma ...
s.


Preparation and handling

Iodomethane is formed via the
exothermic reaction In thermochemistry, an exothermic reaction is a "reaction for which the overall standard enthalpy change Δ''H''⚬ is negative." Exothermic reactions usually release heat. The term is often confused with exergonic reaction, which IUPAC defines ...
that occurs when
iodine Iodine is a chemical element with the Symbol (chemistry), symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , ...
is added to a mixture of
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...
with red
phosphorus Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Ea ...
. The iodinating reagent is phosphorus triiodide that is formed ''in situ:'' :3 CH3OH + PI3 → 3 CH3I + H2PO3H Alternatively, it is prepared from the reaction of
dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent ...
with potassium iodide in the presence of calcium carbonate: : (CH3O)2SO2 + KI → CH3I + CH3OSO2OK Iodomethane can also be prepared by the reaction of methanol with aqueous
hydrogen iodide Hydrogen iodide () is a diatomic molecule and hydrogen halide. Aqueous solutions of HI are known as hydroiodic acid or hydriodic acid, a strong acid. Hydrogen iodide and hydroiodic acid are, however, different in that the former is a gas under ...
: : CH3OH + HI → CH3I + H2O The generated iodomethane can be distilled from the reaction mixture. Iodomethane may also be prepared by treating
iodoform Iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the chemical formula C H I3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older ch ...
with
potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...
and
dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent ...
under 95%
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
.


Storage and purification

Like many organoiodide compounds, iodomethane is typically stored in dark bottles to inhibit degradation caused by light to give iodine, giving degraded samples a purplish tinge. Commercial samples may be stabilized by copper or silver wire. It can be purified by washing with Na2S2O3 to remove iodine followed by distillation.


Biogenic iodomethane

Most iodomethane is produced by microbial methylation of iodide. Oceans are the major source, but rice paddies are also significant.


Reactions


Methylation reagent

Iodomethane is an excellent substrate for SN2 substitution reactions. It is
sterically Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivity of ions ...
open for attack by
nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they ar ...
s, and
iodide An iodide ion is the ion I−. Compounds with iodine in formal oxidation state −1 are called iodides. In everyday life, iodide is most commonly encountered as a component of iodized salt, which many governments mandate. Worldwide, iodine de ...
is a good
leaving group In chemistry, a leaving group is defined by the IUPAC as an atom or group of atoms that detaches from the main or residual part of a substrate during a reaction or elementary step of a reaction. However, in common usage, the term is often limited ...
. It is used for alkylating carbon, oxygen, sulfur, nitrogen, and phosphorus nucleophiles. Unfortunately, it has a high equivalent weight: one mole of iodomethane weighs almost three times as much as one mole of
chloromethane Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula . One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial ...
and nearly 1.5 times as much as one mole of
bromomethane Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H3 Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozo ...
. On the other hand,
chloromethane Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula . One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial ...
and
bromomethane Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H3 Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozo ...
are gaseous, thus harder to handle, and are also weaker alkylating agents. Iodide can act as a catalyst when reacting chloromethane or bromomethane with a nucleophile while iodomethane is formed in ''situ''. Iodides are generally expensive relative to the more common chlorides and bromides, though iodomethane is reasonably affordable; on a commercial scale, the more toxic
dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent ...
is preferred, since it is cheap and has a higher boiling point. The iodide leaving group in iodomethane may cause unwanted side reactions. Finally, being highly reactive, iodomethane is more dangerous for laboratory workers than related chlorides and bromides. For example, it can be used for the methylation of
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...
s or
phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are ...
: : In these examples, the base ( K2CO3 or Li2CO3) removes the acidic proton to form the
carboxylate In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxylat ...
or
phenoxide Phenolates (also called phenoxides) are anions, salts, and esters of phenols. They may be formed by reaction of phenols with strong base. Properties Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic ...
anion, which serves as the nucleophile in the SN2 substitution. Iodide is a "soft" anion which means that methylation with MeI tends to occur at the "softer" end of an ambidentate
nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they ar ...
. For example, reaction with
thiocyanate Thiocyanate (also known as rhodanide) is the anion . It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Mercury(II) thiocyanate was formerly used in pyr ...
ion favours attack at sulfur rather than "hard" nitrogen, leading mainly to methyl thiocyanate (CH3SCN) rather than methyl isothiocyanate CH3NCS. This behavior is relevant to the
methylation In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These ...
of stabilized
enolate In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl () compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds. Bonding and structure Enolate anions are electr ...
s such as those derived from 1,3-dicarbonyl compounds. Methylation of these and related enolates can occur on the harder
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...
atom or the (usually desired) carbon atom. With iodomethane, C-alkylation nearly always predominates.


Other reactions

In the Monsanto process and the
Cativa process The Cativa process is a method for the production of acetic acid by the carbonylation of methanol. The technology, which is similar to the Monsanto process, was developed by BP Chemicals and is under license by BP Plc. The process is based on an ...
, MeI forms ''in situ'' from the reaction of
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...
and
hydrogen iodide Hydrogen iodide () is a diatomic molecule and hydrogen halide. Aqueous solutions of HI are known as hydroiodic acid or hydriodic acid, a strong acid. Hydrogen iodide and hydroiodic acid are, however, different in that the former is a gas under ...
. The CH3I then reacts with
carbon monoxide Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simpl ...
in the presence of a
rhodium Rhodium is a chemical element with the symbol Rh and atomic number 45. It is a very rare, silvery-white, hard, corrosion-resistant transition metal. It is a noble metal and a member of the platinum group. It has only one naturally occurring i ...
or
iridium Iridium is a chemical element with the symbol Ir and atomic number 77. A very hard, brittle, silvery-white transition metal of the platinum group, it is considered the second-densest naturally occurring metal (after osmium) with a density o ...
complex to form acetyl iodide, the precursor to
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...
after
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
. The Cativa process is usually preferred because less water is required to use and there are less byproducts. MeI is used to prepare the
Grignard reagent A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . ...
, methylmagnesium iodide ("MeMgI"), a common source of "Me". The use of MeMgI has been somewhat superseded by the commercially available methyllithium. MeI can also be used to prepare
dimethylmercury Dimethylmercury (( C H3)2 Hg) is an extremely toxic organomercury compound. A highly volatile, reactive, flammable, and colorless liquid, dimethylmercury is one of the strongest known neurotoxins, with a quantity of less than 0.1 mL capable of in ...
, by reacting 2 moles of MeI with a 2/1-molar sodium
amalgam Amalgam most commonly refers to: * Amalgam (chemistry), mercury alloy * Amalgam (dentistry), material of silver tooth fillings ** Bonded amalgam, used in dentistry Amalgam may also refer to: * Amalgam Comics, a publisher * Amalgam Digital, an in ...
(2 moles of sodium, 1 mol of mercury). Iodomethane and other organic iodine compounds do form under the conditions of a serious nuclear accident, after both
Chernobyl Chernobyl ( , ; russian: Чернобыль, ) or Chornobyl ( uk, Чорнобиль, ) is a partially abandoned city in the Chernobyl Exclusion Zone, situated in the Vyshhorod Raion of northern Kyiv Oblast, Ukraine. Chernobyl is about n ...
and Fukushima,
Iodine-131 Iodine-131 (131I, I-131) is an important radioisotope of iodine discovered by Glenn Seaborg and John Livingood in 1938 at the University of California, Berkeley. It has a radioactive decay half-life of about eight days. It is associated with n ...
was detected in organic iodine compounds in Europe and Japan respectively.


Use as a pesticide

Iodomethane had also been proposed for use as a
fungicide Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality ...
,
herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...
,
insecticide Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed t ...
, nematicide, and as a soil disinfectant, replacing methyl bromide (also known as
bromomethane Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H3 Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozo ...
) (banned under the
Montreal Protocol The Montreal Protocol is an international treaty designed to protect the ozone layer by phasing out the production of numerous substances that are responsible for ozone depletion. It was agreed on 16 September 1987, and entered into force ...
). Manufactured by Arysta LifeScience and sold under the brand name MIDAS, iodomethane is registered as a pesticide in the U.S., Mexico, Morocco, Japan, Turkey, and New Zealand and registration is pending in Australia, Guatemala, Costa Rica, Chile, Egypt, Israel, South Africa and other countries. The first commercial applications of MIDAS soil fumigant in California began in Fresno County, in May, 2011. Iodomethane had been approved for use as a
pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and ...
by the
United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...
in 2007 as a pre-plant
biocide A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a sli ...
used to control insects, plant parasitic nematodes, soil borne pathogens, and weed seeds.Zitto, Kelly The compound was registered for use as a preplant soil treatment for field grown strawberries, peppers, tomatoes, grape vines, ornamentals and turf and nursery grown strawberries, stone fruits, tree nuts, and conifer trees. After the discovery phase in a consumer lawsuit, the manufacturer withdrew the fumigant citing its lack of market viability."Maker of methyl iodide scraps controversial pesticide"
''San Jose Mercury News'' March 20, 2012
The use of iodomethane as a fumigant has drawn concern. For example, 54 chemists and physicians contacted the U.S. EPA in a letter, saying "We are skeptical of U.S. EPA's conclusion that the high levels of exposure to iodomethane that are likely to result from broadcast applications are 'acceptable' risks. U.S. EPA has made many assumptions about toxicology and exposure in the risk assessment that have not been examined by independent scientific peer reviewers for adequacy or accuracy. Additionally, none of U.S. EPA's calculations account for the extra vulnerability of the unborn fetus and children to toxic insults." EPA Assistant Administrator Jim Gulliford replied saying, "We are confident that by conducting such a rigorous analysis and developing highly restrictive provisions governing its use, there will be no risks of concern," and in October the EPA approved the use of iodomethane as a soil fumigant in the United States. The California Department of Pesticide Regulation (DPR) concluded that iodomethane is "highly toxic," that "any anticipated scenario for the agricultural or structural fumigation use of this agent would result in exposures to a large number of the public and thus would have a significant adverse impact on the public health", and that adequate control of the chemical in these circumstances would be "difficult, if not impossible." Iodomethane was approved as a pesticide in California that December. A lawsuit was filed on January 5, 2011, challenging California's approval of iodomethane. Subsequently, the manufacturer withdrew the fumigant and requested that California Department of Pesticide Regulation cancel its California registration, citing its lack of market viability.


Safety


Toxicity and biological effects

According to the
United States Department of Agriculture The United States Department of Agriculture (USDA) is the federal executive department responsible for developing and executing federal laws related to farming, forestry, rural economic development, and food. It aims to meet the needs of comme ...
iodomethane exhibits moderate to high acute toxicity for inhalation and ingestion. The
Centers for Disease Control and Prevention The Centers for Disease Control and Prevention (CDC) is the national public health agency of the United States. It is a United States federal agency, under the Department of Health and Human Services, and is headquartered in Atlanta, Georg ...
(CDC) lists inhalation, skin absorption, ingestion, and eye contact as possible exposure routes with target organs of the eyes, skin, respiratory system, and the
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all p ...
. Symptoms may include eye irritation, nausea, vomiting, dizziness,
ataxia Ataxia is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in eye movements. Ataxia is a clinical manifestation indicating dysfunction of ...
, slurred speech, and
dermatitis Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved c ...
. In high dose acute toxicity, as may occur in industrial accidents, toxicity includes metabolic disturbance, renal failure, venous and arterial thrombosis and encephalopathy with seizures and coma, with a characteristic pattern of brain injury. Iodomethane has an for oral administration to rats 76 mg/kg, and in the
liver The liver is a major organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the synthesis of proteins and biochemicals necessary for digestion and growth. In humans, it i ...
it undergoes rapid conversion to S-methyl
glutathione Glutathione (GSH, ) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, pe ...
. In its risk assessment of iodomethane, the U.S. EPA conducted an exhaustive scientific and medical literature search over the past 100 years for reported cases of human poisonings attributable to the compound. Citing the EPA as its source, the California Department of Pesticide Regulation concluded, "Over the past century, only 11 incidents of iodomethane poisoning have been reported in the published literature." (Hermouet, C. ''et al.'' 1996 & Appel, G.B. ''et al.'' 1975) "An updated literature search on May 30, 2007 for iodomethane poisoning produced only one additional case report." (Schwartz MD, ''et al.'' 2005). All but one were industrial—not agricultural—accidents, and the remaining case of poisoning was an apparent suicide. Iodomethane is routinely and regularly used in industrial processes as well as in most university and college chemistry departments for study and learning related to a variety of organic chemical reactions.


Carcinogenicity in mammals

It is considered a potential occupational carcinogen by the U.S.
National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...
(NIOSH), the U.S.
Occupational Safety and Health Administration The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agen ...
and the U.S.
Centers for Disease Control and Prevention The Centers for Disease Control and Prevention (CDC) is the national public health agency of the United States. It is a United States federal agency, under the Department of Health and Human Services, and is headquartered in Atlanta, Georg ...
. The
International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...
concluded based on studies performed after methyl iodide was Proposition 65 listed that: "Methyl iodide is not classifiable as to its carcinogenicity to humans (Group 3)." the
Environmental Protection Agency A biophysical environment is a biotic and abiotic surrounding of an organism or population, and consequently includes the factors that have an influence in their survival, development, and evolution. A biophysical environment can vary in scale ...
classifies it as "not likely to be carcinogenic to humans in the absence of altered thyroid hormone homeostasis," i.e. it is a human carcinogen but only at doses large enough to disrupt thyroid function (via excess iodide). However this finding is disputed by the
Pesticide Action Network Pesticide Action Network (PAN) is "an international coalition of around 600 NGO A non-governmental organization (NGO) or non-governmental organisation (see spelling differences) is an organization that generally is formed independent from ...
which states that the EPA's cancer rating "appears to be based solely on a single rat inhalation study in which 66% of the control group and 54-62% of the rats in the other groups died before the end of the study". They go on to state: "The EPA appears to be dismissing early peer-reviewed studies in favor of two nonpeer-reviewed studies conducted by the registrant that are flawed in design and execution." Despite requests by the U.S. EPA to the
Pesticide Action Network Pesticide Action Network (PAN) is "an international coalition of around 600 NGO A non-governmental organization (NGO) or non-governmental organisation (see spelling differences) is an organization that generally is formed independent from ...
to bring forth scientific evidence of their claims, they have not done so.


References


Additional sources

* * Sulikowski, G. A.; Sulikowski, M. M. (1999). in Coates, R.M.; Denmark, S. E. (Eds.) ''Handbook of Reagents for Organic Synthesis, Volume 1: Reagents, Auxiliaries and Catalysts for C-C Bond Formation'' New York: Wiley, pp. 423–26. *


External links

* * * IARC Summaries & Evaluations





* * {{Authority control Iodoalkanes Halomethanes Methylating agents IARC Group 3 carcinogens Environmental controversies Environmental effects of pesticides Pesticides in the United States Halogen-containing natural products Iodine-containing natural products