Ethanethiol

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Ethanethiol

Ethanethiol is the organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
with the formula CH₃CH₂SH. It consists of an ethyl group, CH₃CH₂, attached to a thiol

Thiol

In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom . Being the sulfur analogue of an alcohol group , this functional group is referred to either as a thiol group or a sulfhydryl group....
group, SH. The compound is structurally similar to ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
by replacement of O

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
by S

Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
. This change leads to many different properties, the most infamous of which is the strong odour of EtSH. Ethanethiol is also more volatile

Volatility (chemistry)

Volatility in the context of chemistry, physics and thermodynamics is a measure of the tendency of a substance to vaporize. It has also been defined as a measure of how readily a substance vaporizes....
than ethanol due to its diminished ability to engage in hydrogen bonding.

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Odour

Ethanethiol has a strongly disagreeable odour

Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
that humans can detect in minute concentrations. The threshold for human detection is as low as one part in 2.8 billion parts of air. Its odour resembles that of leek

Leek

The leek, Allium ampeloprasum var. porrum , also sometimes known as Allium porrum, is a vegetable which belongs, along with the onion and garlic, to the Alliaceae family....
s or onion

Onion

Onion is a term used for many plants in the genus Allium. They are known by the common name "onion" but, used without qualifiers, it usually refers to Allium cepa....
s. Ethanethiol is intentionally added to butane

Butane

Butane, also called n-butane, is the unbranched alkane with four carbon atoms, CH3CH2CH2CH3....
and propane

Propane

Propane is a three-carbon alkane, normally a gas, but compressible to a transportable liquid. It is derived from other petroleum products during oil or natural gas processing....
(see: LPG) to impart an easily noticed smell to these odourless fuels, that otherwise pose the threat of fire

Fire

Fire is the oxidation of a combustion material releasing heat, light, and various Chemical reaction products such as carbon dioxide and water....
and explosion

Explosion

An explosion is a sudden increase in volume and release of energy in an extreme manner, usually with the generation of high temperatures and the release of gases....
.

According to the 2000 edition of the Guinness Book Of World Records, ethanethiol is the "smelliest substance" in existence. Other more specialised chemicals were probably not examined, however. Most volatile thiols are comparably offensive. Thiols can be oxidized to sulfoxides, which have only a faint smell, using bleach

Bleach

A bleach is a chemical that removes colors or whitens, often via oxidation. Common chemical bleaches include household "chlorine bleach", a solution of approximately 3?6% sodium hypochlorite , and "oxygen bleach", which contains hydrogen peroxide or a peroxide-releasing compound such as sodium perborate, sodium percarbonate, sodium persulfat...
or related oxidants.

Reactions

Ethanethiol is a valued reagent

Reagent

A reagent or reactant is a substance or compound consumed during a chemical reaction. Solvents and catalysts, although they are involved in the reaction, are usually not referred to as reactants....
in organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
. In the presence of sodium hydroxide

Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
, it forms the powerful nucleophile

Nucleophile

In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding electrons. Because nucleophiles donate electrons, they are by definition Lewis bases ....
NaSEt. The salt can also be generated quantitatively by reaction with sodium hydride

Sodium hydride

Sodium hydride is the chemical compound with the formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H- ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water....
.

Mild oxidation of EtSH gives the disulfide

Disulfide

In chemistry, a disulfide usually refers to the structural unit composed of a linked pair of sulfur atoms. The disulfide anion is S22-....
, diethyl disulfide:

2 EtSH + H₂O₂

Hydrogen peroxide

Hydrogen peroxide is a very pale blue liquid which appears colorless in a dilute solution, slightly more viscous than water. It is a weak acid....
→ EtS-SEt + 2 H₂O

Like other thiols, it behaves comparably to hydrogen sulfide

Hydrogen sulfide

Hydrogen sulfide is the chemical compound with the chemical formula Hydrogen2Sulfur. This colorless, toxic and flammable gas is partially responsible for the foul odor of egg and flatulence....
. For example, it binds, concomitant with deprotonation to "soft" transition metal cations, such as Hg²⁺, Cu⁺, and Ni²⁺ to give polymeric thiolato complexes, Hg(SEt)₂, CuSEt, and Ni(SEt)₂, respectively.

Ethanethiol

Odour

Reactions

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