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Ethanethiol is the
organic compound with the formula CH
3CH
2SH. It consists of an ethyl group, CH
3CH
2, attached to a
thiol group, SH. The compound is structurally similar to
ethanol by replacement of
O by
S. This change leads to many different properties, the most infamous of which is the strong odour of EtSH. Ethanethiol is also more
volatile than ethanol due to its diminished ability to engage in
hydrogen bonding. Ethanethiol is toxic. It occurs naturally as a minor component of
petroleum, and may be added to
liquefied petroleum gas (LPG) to warn of a gas leak. At these concentrations, ethanethiol isn't harmful.
Odour
Ethanethiol has a strongly disagreeable
odour 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
leeks. Ethanethiol is intentionally added to
butane and
propane (see:
LPG) to impart an easily noticed smell to these odourless fuels, that otherwise pose the threat of
fire and
explosion.
According to the 2000 edition of the
Guinness Book Of World Records, ethanethiol is the "smelliest substance" in existence. Other more specialized chemicals were probably not examined, however. Most volatile thiols are comparably offensive. Thiols can be oxidized, and thus de-odourized, using
bleach or related oxidants.
Reactions
Ethanethiol is a valued
reagent in
organic synthesis. In the presence of
sodium hydroxide, it forms the powerful
nucleophile NaSEt. The salt can also be generated quantitatively by reaction with
sodium hydride.
Oxidation of EtSH gives the
disulfide,
diethyl disulfide:
» 2 EtSH +
H2O2 → EtS-SEt + 2 H
2O
Like other thiols, it behaves comparably to
hydrogen sulfide. For example, it binds, concomitant with deprotonation to "soft" transition metal
cations, such a Hg
2+, Cu
+, and Ni
2+ to give polymeric thiolato complexes, Hg(SEt)
2, CuSEt, and Ni(SEt)
2, respectively.
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