Furfuryl Mercaptan

Product Name:

Furfuryl mercaptan

Synonyms:

(2-furanyl)methylmercaptan;2-(mercaptomethyl)furan;2-furfurylmercaptan;2-Furfurylthiol;2-Furylmethyl mercaptan;2-furylmethylmercaptan;2-mercaptomethylfuran;-Furylmethyl mercaptan

CAS:

98-02-2

MF:

C5H6OS

MW:

114.17

EINECS:

202-628-2

Product Categories:

Sulfides flavors;Furans;thiol Flavor

Mol File:

98-02-2.mol

Melting point 

157.5 °C

Boiling point 

155 °C(lit.)

density 

1.132 g/mL at 25 °C(lit.)

FEMA 

2493 | FURFURYL MERCAPTAN

refractive index 

n20/D 1.531(lit.)

Fp 

113 °F

storage temp. 

Flammables area

pka

9.59±0.10(Predicted)

form 

Liquid

color 

Clear colorless to pale yellow

Water Solubility 

insoluble

Sensitive 

Air Sensitive

JECFA Number

1072

BRN 

383594

CAS DataBase Reference

98-02-2(CAS DataBase Reference)

NIST Chemistry Reference

2-Furanmethanethiol(98-02-2)

EPA Substance Registry System

2-Furanmethanethiol (98-02-2)

Hazard Codes 

F,Xn

Risk Statements 

10-36/37-20/21/22

Safety Statements 

23-24/25-16-36-26-7/9

RIDADR 

UN 3336 3/PG 3

WGK Germany 

3

RTECS 

LU2100000

F 

10-13-23

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29321900

Description

Furfuryl mercaptan has a characteristic unpleasant odor. It is prepared by reacting thiourea and furfuryl chloride with subsequent hydrolysis of the reaction product; also by reduction of difurfuryl disulfide in alcoholic solution using zinc dust and a small amount of acetic acid or using activated alumina. Furfuryl mercaptan tends to polymerize when heated in the presence of mineral acids.

Chemical Properties

Furfuryl mercaptan has a characteristic unpleasant odor.

Chemical Properties

clear colorless to pale yellow liquid

Chemical Properties

2-Furylmethanethiol is an important constituent of the aroma of roasted coffee. It is a liquid with an unpleasant odor, which becomes like coffee when diluted.

Uses

Furfuryl Mercaptam is a volatile flavor component of corn tortilla chips.

Preparation

Furfuryl mercaptan is prepared from furfuryl alcohol, thiourea, and hydrogen chloride.The resulting S-furfurylisothiouronium chloride is cleaved with sodium hydroxide to give furfuryl mercaptan.

Aroma threshold values

Detection: 0.005 to 0.01 ppb; aroma characteristics at 0.01%: intense sulfurous onion impact, lacrimator, slightly skunk-like with a dairy nuance and a hint of savory and coffee-like notes.

Taste threshold values

Taste characteristics at 0.2 to 1 ppb: sulfureous, roasted, onion, garlic and coffee.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Used as a flavoring in chocolate, fruit, nuts, and coffee. When heated to decomposition it emits toxic fumes of SOx. See also MERCAPTANS.

Chemical Synthesis

Prepared by reacting thiourea and furfuryl chloride with subsequent hydrolysis of the reaction product; also by reduction of difurfuryl disulfde in alcoholic solution using zinc dust and a small amount of acetic acid or using activated alumina.

Raw materials

Etanol-->Sodium hydroxide-->Formaldehyde-->Phosphorus pentasulfide-->CHLOROETHANE-->Sodium hydrosulfide-->2-Chloromethylfuran

Preparation Products

Phorate-->Furfuryl methyl sulfide-->4-[(2-FURYLMETHYL)THIO]-3-NITROBENZALDEHYDE-->Difurfurylsulfide