2-Naphthalenethiol

Description

2-Naphthalenthiol has a disagreeable mercaptan-like odor. May be prepared by catalytic hydrogenation of a sulfonic acid derivative of naphthalene; by reduction of naphthalenesulfonyl chloride with zinc.

Chemical properties

Almost white to cream powder

Chemical properties

2-Naphthyl mercaptan has a disagreeable sulfurous, mushroom, meaty odor

The Uses of 2-Naphthalenethiol

2-Thionaphthol was used in the preparation of cholesterol monolayer and multilayer Langmuir- Blodgett (LB) films. The magnetic resonance shift for a self-assembled monolayer of 2-naphthalenethiol was studied that suggested considerable promise in flexible and transparent photonic devices for biological and chemical sensing.

Preparation

By catalytic hydrogenation of a sulfonic acid derivative of naphthalene; by reduction of naphthalenesulfonyl chloride with zinc.

Definition

ChEBI: 2-Naphthalenethiol is a member of naphthalenes.

Taste threshold values

Taste characteristics at 10 ppm: sulfurous, meaty, brown, roasted, chicken, eggy with a slight nutty nuance

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 3980, 1966 DOI: 10.1021/jo01350a023
Tetrahedron Letters, 37, p. 4523, 1996 DOI: 10.1016/0040-4039(96)00873-8

General Description

The magnetic resonance shift for a self-assembled monolayer of 2-naphthalenethiol was studied that suggested considerable promise in flexible and transparent photonic devices for biological and chemical sensing.

Safety Profile

Poison by ingestion and intraperitoneal routes. A mosquito larvicide. When heated to decomposition it emits highly toxic fumes of SOx.

Purification Methods

It is steam volatile. It has to be distilled under Ar or N2, as it oxidises to the disulfide, and crystallises from EtOH. The S-methyl derivative has m 104-105o (from *C6H6/pet ether), and the S-ethyl derivative M 188.2, has m 16o and b 175-170.5o/15mm. The S-acetate has m 53.5o and b 191o/15mm, and the diethylamine salt forms yellow needles m 107o from dioxane. [Beilstein 6 H 657, 6 I 316, 6 II 610, 6 III 3006, 6 IV 4312.]