2-Naphthalenethiol Property

Melting point:

79-81 °C (lit.)

Boiling point:

286 °C (lit.)

Density 

1.22

refractive index 

1.589-1.591

FEMA 

3314 | 2-NAPHTHALENTHIOL

Flash point:

69 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

diethyl ether: very soluble(lit.)

form 

Powder

pka

6?+-.0.30(Predicted)

color 

Almost white to cream

Odor

at 0.10 % in propylene glycol. sulfurous rubbery meaty roasted woody creamy artichoke

Odor Type

sulfurous

Water Solubility 

Soluble in alcohol, dipropylene glycol. Soluble in water 34.4 mg/L @ 25°C.

Sensitive 

Air Sensitive

Merck 

14,6379

JECFA Number

531

BRN 

636389

LogP

3.75

CAS DataBase Reference

91-60-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Naphthalenethiol(91-60-1)

EPA Substance Registry System

2-Naphthalenethiol (91-60-1)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-20/21/22

Safety Statements 

36/37

RIDADR 

UN 3335

WGK Germany 

3

RTECS 

QK3930000

F 

13

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HS Code 

29309070

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2-Naphthalenethiol Chemical Properties,Usage,Production

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.]