1-Naphthalenethiol is an

organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

with the formula C₁₀H₇SH. It is a white solid. It is one of two mono

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 of

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

, the other being

2-naphthalenethiol 2-Naphthalenethiol is an organosulfur compound with the formula C10H7SH. It is a white solid. It is one of two monothiols of naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, ...

Synthesis

A practical synthesis involves the tin/HCl-reduction of the naphthalene-1-sulfonyl chloride. 1-Naphthalenethiol can also be prepared from

1-bromonaphthalene 1-Bromonaphthalene is an organic compound with the formula C10H7Br. It is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene. Under normal conditions, the substance is a colorless liquid. Synthesis and reactions It is prep ...

by Pd-catalyzed reaction with the silylthiolate ⁱPr₃SiSK followed by hydrolysis of the silathioether. It was first prepared from the

Grignard reagent Grignard reagents or Grignard compounds are chemical compounds 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 bromi ...

generated from 1-bromonaphthalene. Treatment of that reagent with elemental sulfur followed by acidification gave the compound. It has been produced by the iodine-catalyzed reduction of 1-naphthalenesulfonic acid with

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a l ...

Reactions

Treating 1-naphthalenethiol with

butyl lithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...

in the presence of

tmeda Tetramethylethylenediamine (TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylenediamine by replacement of the four amine hydrogens with four methyl groups. It is a colorless liquid, ...

affords the 2-lithio derivative.

References

{{DEFAULTSORT:Naphthalenethiol, 1- Thiols 1-Naphthyl compounds Foul-smelling chemicals