2-Thiophenethiol Chemical Properties

Boiling point:

129 °C(lit.)

Density 

1.252 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.62(lit.)

FEMA 

3062 | 2-THIENYL MERCAPTAN

Flash point:

150 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Chloroform, DMSO

form 

clear liquid

pka

6.38±0.43(Predicted)

color 

Light yellow to Brown

Odor

at 0.10 % in dipropylene glycol. burnt caramel roasted coffee

Odor Type

caramellic

Sensitive 

Air Sensitive

JECFA Number

1052

BRN 

104650

InChIKey

SWEDAZLCYJDAGW-UHFFFAOYSA-N

LogP

2.20

CAS DataBase Reference

7774-74-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Thiophenethiol(7774-74-5)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36/38-21/22-20/22

Safety Statements 

26-36-36/37/39

RIDADR 

UN3334

WGK Germany 

3

F 

10-13-23

Hazard Note 

Irritant

HazardClass 

9

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:2-Mercaptothiophene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Thiophenethiol Usage And Synthesis

Chemical Properties

Clear yellowish to orange liquid

Chemical Properties

2-Thienyl mercaptan has a very unpleasant, burnt caramellic and sulfuraceous odor with a similar flavor.

Uses

2-Thiophenethiol is used in biological studies to evaluate the changes in key odorants of hazelnut induced by roasting.

Definition

ChEBI: Thiophene-2-thiol is a heteroarene.

Preparation

By heating sodium sulfosuccinate with phosphorous trichloride; also by reduction of thiophene-2-sulfonyl chloride.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 6316, 1953 DOI: 10.1021/ja01120a518

Synthesis

A three-necked flask fitted with a mechanical stirrer and a 600-ml dropping funnel filled with dry nitrogen is charged with 500 ml of tetrahydrofuran and 56 g (53 ml, 0.67 mole) of thiophene. This mixture is stirred under nitrogen and cooled to ?40° with an acetone–dried ice bath while 490 ml (0.662 mole) of 1.35 M n-butyllithium in pentane is added over 5 minutes via the dropping funnel. The mixture's temperature is held between ?30° and ?20° for 1 hour, then lowered to ?70° by adding dry ice to the bath. Powdered sulfur crystals (20.4 g, 0.638 g) are added to the stirred mixture in one aliquot. After 30 minutes, the temperature is allowed to rise to ?10°, and then the yellow solution is carefully poured into 1 l of rapidly stirred ice water. These aqueous extracts are combined with the aqueous layer, and the whole is chilled and carefully acidified with 4 N sulfuric acid. This aqueous phase is immediately extracted with three 200-ml portions of diethyl ether. The combined ether extracts are washed twice with 100 ml portions of water to remove acid and remaining tetrahydrofuran and dried over anhydrous sodium sulfate. After the removal of ether, the residual golden-brown oil is purified by distillation at reduced pressure. The portion boiling at 53–56° (5 mm) is collected, yielding 49.5–53.5 g (65–70%) of 2-thiophenethiol as a yellow oil.

2-Thiophenethiol(7774-74-5)Related Product Information

• PYRITHIOXIN DIHYDROCHLORIDE
• Thiophene
• Ethanethiol
• 1-Dodecanethiol
• 1,2-Ethanedithiol
• METHYL MERCAPTAN
• Sodium thiomethoxide
• PYRITHIOXIN
• 2-Ethylhexyl 10-ethyl-4-[[2-[(2-ethylhexyl)oxy]-2-oxoethyl]thio]-4-methyl-7-oxo-8-oxa-3,5-dithia-4-stannatetradecanoate
• 2-BENZENESULFONYLTHIOPHENE
• 5-[(BENZOYLAMINO)METHYL]THIOPHENE-2-SULFONYL CHLORIDE
• 4,5-Dibromothiophene-2-sulphonyl chloride
• 5-Chlorothiophene-2-sulfonyl chloride
• 4-(BENZENESULFONYL)THIOPHENE-2-SULFONYL CHLORIDE
• 4-BROMO-5-CHLOROTHIOPHENE-2-SULFONYL CHLORIDE
• 5-(PHENYLSULFONYL)THIOPHENE-2-SULFONYL CHLORIDE
• 3-BROMO-5-CHLOROTHIOPHENE-2-SULFONYL CHLORIDE
• 2-Thiophenesulfonyl chloride