Dimethylamine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula (CH₃)₂NH. This

secondary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...

is a colorless, flammable gas with an

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...

-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

Structure and synthesis

The molecule consists of a

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, and ...

with two

methyl 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 many ...

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...

s and one

proton A proton is a stable subatomic particle, symbol , H+, or 1H+ with a positive electric charge of +1 ''e'' elementary charge. Its mass is slightly less than that of a neutron and 1,836 times the mass of an electron (the proton–electron mass ...

. Dimethylamine is a

weak base A weak base is a base that, upon dissolution in water, does not dissociate completely, so that the resulting aqueous solution contains only a small proportion of hydroxide ions and the concerned basic radical, and a large proportion of undissociat ...

and the pKa of the

ammonium The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary a ...

CH₃--CH₃ is 10.73, a value above

methylamine Methylamine is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold as a solution in methanol, ...

(10.64) and

trimethylamine Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a colorless, hygroscopic, and flammable tertiary amine. It is a gas at room temperature but is usually sold as a 40% solution in water. (It is also sold in pressurized ...

(9.79). Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by

catalytic Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

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 a ...

and

at elevated temperatures and high pressure: :2 CH₃OH + NH₃ → (CH₃)₂NH + 2 H₂O

Natural occurrence

Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of a few mg/kg.

Uses

Dimethylamine is a precursor to several industrially significant compounds. It reacts with

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non ...

to give dimethyl

dithiocarbamate In organic chemistry, a dithiocarbamate is a functional group with the general formula and structure . It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms (when only 1 oxygen is replaced the result is thioca ...

, a precursor to

zinc bis(dimethyldithiocarbamate) Zinc dimethyldithiocarbamate is a coordination complex of zinc with dimethyldithiocarbamate. It is a pale yellow solid that is used as a fungicide, the sulfur vulcanization of rubber, and other industrial applications. Applications Known as zir ...

and other chemicals used in the sulfur vulcanization of

rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, and ...

. The solvents

dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...

and dimethylacetamide are derived from dimethylamine. It is raw material for the production of many agrichemicals and

pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and re ...

s, such as

dimefox Dimefox was an organophosphate pesticide. In its pure form it is a colourless liquid with a fishy odour. Dimefox was first produced in 1940 by the group of Gerhard Schrader in Germany. It was historically used as a pesticide, but has been deeme ...

and

diphenhydramine Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremor in parkinsonism, and nausea. It is taken by mouth, injected into a vein ...

, respectively. The

chemical weapon A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...

tabun is derived from dimethylamine. The

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

lauryl dimethylamine oxide is found in

soap Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are use ...

s and cleaning compounds.

Unsymmetrical dimethylhydrazine Unsymmetrical dimethylhydrazine (UDMH; 1,1-dimethylhydrazine, НДМГ or codenamed Geptil) is a chemical compound with the formula H2NN(CH3)2 that is used as a rocket propellant. It is a colorless liquid, with a sharp, fishy, ammonia-like smell ...

, a rocket fuel, is prepared from dimethylamine. :(CH₃)₂NH + NH₂Cl → (CH₃)₂NNH₂ ⋅ HCl

Reactions

It is basic, in both the Lewis and Brønsted senses. It easily forms dimethylammonium salts upon treatment with acids. Deprotonation of dimethylamine can be effected with organolithium compounds. The resulting LiNMe₂, which adopts a cluster-like structure, serves as a source of "Me₂N⁻". This lithium amide has been used to prepare volatile metal complexes such as tetrakis(dimethylamido)titanium and pentakis(dimethylamido)tantalum. It is also a Lewis base. It reacts with many carbonyl compounds. Aldehydes give aminals. For example reaction of dimethylamine and

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

gives bis(dimethylamino)methane: : 2 (CH₃)₂NH + CH₂O → CH₃)₂Nsub>2CH₂ + H₂O It converts esters to dimethylamides. Dimethylamine undergoes

nitrosation Nitrosation is a process of converting organic compounds into nitroso derivatives, i.e. compounds containing the R-NO functionality. ''C''-Nitroso compounds ''C''-Nitroso compounds, such as nitrosobenzene, are typically prepared by oxidation of ...

to give dimethylnitrosamine, a carcinogen.

Occurrence

It is an attractant for

boll weevil The boll weevil (''Anthonomus grandis'') is a beetle that feeds on cotton buds and flowers. Thought to be native to Central Mexico, it migrated into the United States from Mexico in the late 19th century and had infested all U.S. cotton-growing ...

s.''The Merck Index, 10th Ed.'' (1983), p.470, Rahway: Merck & Co.

Safety

Dimethylamine is not very toxic with the following LD₅₀ values: 736 mg/kg (mouse, i.p.); 316 mg/kg (mouse, p.o.); 698 mg/kg (rat, p.o.); 3900 mg/kg (rat, dermal); 240 mg/kg (guinea pig or rabbit, p.o.).Chemical Information Profile for Dimethylamine Borane, National Toxicology Program, NIEHS, NIH (2008), p.4: http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/DimethylamineBorane508.pdf

References

External links

* (gas) * (aqueous solution) *
Properties
from

Air Liquide Air Liquide S.A. (; ; literally "liquid air"), is a French multinational company which supplies industrial gases and services to various industries including medical, chemical and electronic manufacturers. Founded in 1902, after Linde it is ...

MSDS A safety data sheet (SDS), material safety data sheet (MSDS), or product safety data sheet (PSDS) is a document that lists information relating to occupational safety and health for the use of various substances and products. SDSs are a widely ...

a
airliquide.com
{{Authority control Alkylamines Insect pheromones Insect ecology Secondary amines