2-Naphthalenethiol

2-Naphthalenethiol
  • CAS No.:91-60-1
Other grades of this product :
2-Naphthalenethiol Basic information
Product Name:2-Naphthalenethiol
Synonyms:2-Metcaptonaphthalene;2-Naphthyl thiol;2-naphthylthiol;beta-Mercaptonaphthalene;beta-Naphthyl mercaptan;beta-naphthylmercaptan;mercaptanbeta-naphtalenique;naphthalenethiol(non-specificname)
CAS:91-60-1
MF:C10H8S
MW:160.24
EINECS:202-082-5
Product Categories:Industrial/Fine Chemicals;Phenol&Thiophenol&Mercaptan
Mol File:91-60-1.mol
2-Naphthalenethiol Chemical Properties
Melting point 79-81 °C (lit.)
Boiling point 286 °C (lit.)
density 1.22
refractive index 1.589-1.591
FEMA 3314 | 2-NAPHTHALENTHIOL
Fp 69 °C
storage temp. Inert atmosphere,Room Temperature
solubility diethyl ether: very soluble(lit.)
form Powder
pka6?+-.0.30(Predicted)
color Almost white to cream
Water Solubility Soluble in alcohol, dipropylene glycol. Soluble in water 34.4 mg/L @ 25°C.
Sensitive Air Sensitive
Merck 14,6379
JECFA Number531
BRN 636389
CAS DataBase Reference91-60-1(CAS DataBase Reference)
NIST Chemistry Reference2-Naphthalenethiol(91-60-1)
EPA Substance Registry System2-Naphthalenethiol (91-60-1)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-20/21/22
Safety Statements 36/37
RIDADR UN 3335
WGK Germany 3
RTECS QK3930000
13
Hazard Note Harmful/Irritant
TSCA Yes
HS Code 29309070
MSDS Information
ProviderLanguage
2-Naphthalenethiol English
SigmaAldrich English
ACROS English
ALFA English
2-Naphthalenethiol Usage And Synthesis
Description2-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 Properties2-Naphthyl mercaptan has a disagreeable sulfurous, mushroom, meaty odor
Chemical PropertiesAlmost white to cream powder
Uses2-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.
PreparationBy catalytic hydrogenation of a sulfonic acid derivative of naphthalene; by reduction of naphthalenesulfonyl chloride with zinc.
Taste threshold valuesTaste 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/jo01350a023Tetrahedron Letters, 37, p. 4523, 1996 DOI: 10.1016/0040-4039(96)00873-8
General DescriptionThe 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 ProfilePoison by ingestion and intraperitoneal routes. A mosquito larvicide. When heated to decomposition it emits highly toxic fumes of SOx.
Purification MethodsIt 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.]

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