1-Butanethiol, also known as butyl mercaptan, is a volatile, clear to yellowish

liquid A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, ...

with a fetid (extremely foul-smelling) odor, commonly described as "

skunk Skunks are mammals in the family Mephitidae. They are known for their ability to spray a liquid with a strong, unpleasant scent from their anal glands. Different species of skunk vary in appearance from black-and-white to brown, cream or gin ...

" odor. In fact, 1-butanethiol is structurally similar to several major constituents of a skunk's defensive spray but is not actually present in the spray. The scent of 1-butanethiol is so strong that the human nose can easily detect it in the air at concentrations as low as 10 parts per billion. The threshold level for 1-butanethiol is reported as 1.4 ppb

Chemistry

1-Butanethiol is chemically classified among the

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...

s, which are

organic compounds 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 s ...

with

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

s and

structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bond ...

s similar to

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of se ...

s, except that the

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formul ...

-containing

sulfhydryl group In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...

(-SH) replaces the

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 as ...

-containing

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

(-OH) in the molecule. 1-Butanethiol's basic molecular formula is C₄H₉SH, and its structural formula is similar to that of the alcohol ''n''-butanol. 1-Butanethiol is prepared by the free radical catalyzed addition of hydrogen sulfide to 1-butene. Commercially, this is performed using ultraviolet light. 1-Butanethiol is a thiol of low

molecular weight A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...

, and it is highly

flammable A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...

Uses

1-Butanethiol is used as an industrial solvent, and as an intermediate for cotton defoliants. It is sometimes placed in the "

stink bomb A stink bomb, sometimes called a stinkpot, is a device designed to create an unpleasant smell. They range in effectiveness from being used as simple pranks to military grade malodorants or riot control chemical agents. History A stink bomb t ...

s" and "stink perfumes" for pranksters.

Safety

1-Butanethiol is a very noxious and caustic chemical compound, and at sufficiently high concentrations, it produces serious health effects in both humans and animals, especially as a result of prolonged exposure. Higher concentrations can lead to unconsciousness and coma after prolonged exposure. Contact with the skin and mucous membranes causes burns, and contact with the eyes can lead to blurred vision or complete blindness. Inhalation may cause weakness, confusion, cough, dizziness, drowsiness, headache, nausea, vomiting, and shortness of breath. The substance irritates the eyes, the skin, and the respiratory tract. It may cause effects on the thyroid and the nervous system and could cause lowering of consciousness.

Notes

References

U.S. Department of Labor

HazMap

External links