| 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 | 2-Naphthyl mercaptan has a disagreeable sulfurous, mushroom, meaty odor |
| Chemical Properties | Almost white to cream powder |
| Uses | 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.] |
