2-Naphthalenethiol is an

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

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 gro ...

s of

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

, the other being 1-naphthalenethiol.

Synthesis and reactions

2-Naphthalenethiol is prepared from 2-naphthol by the

Newman–Kwart rearrangement The Newman–Kwart rearrangement is a type of rearrangement reaction in which the aryl group of an ''O''-aryl thiocarbamate, ArOC(=S)NMe2, migrates from the oxygen atom to the sulfur atom, forming an ''S''-aryl thiocarbamate, ArSC(=O)NMe2. The re ...

starting from a

thiocarbamate In organic chemistry, thiocarbamates (thiourethanes) are a family of organosulfur compounds. As the prefix ''thio-'' suggests, they are sulfur analogues of carbamates. There are two isomeric forms of thiocarbamates: ''O''-thiocarbamates, (ester ...

. It undergoes lithiation at the 1 and 3-position. It can be used as a flavouring agent.

References

{{DEFAULTSORT:Naphthalenethiol, 2- Thiols 2-Naphthyl compounds