Benzyl mercaptan Chemical Properties

Melting point:

-29 °C

Boiling point:

194-195 °C (lit.)

Density 

1.058 g/mL at 25 °C (lit.)

vapor density 

>4 (vs air)

refractive index 

n20/D 1.575(lit.)

FEMA 

2147 | BENZYL MERCAPTAN

Flash point:

158 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

pka

9.43(at 25℃)

color 

Clear colorless to light yellow

Odor

at 0.10 % in propylene glycol. sharp alliaceous onion sulfurous garlic horseradish mint coffee

Odor Type

alliaceous

explosive limit

1%(V)

Water Solubility 

Not miscible or difficult to mix in water.

Sensitive 

Air Sensitive

Merck 

14,9322

JECFA Number

526

BRN 

605864

Stability:

Stable. Combustible.

InChIKey

UENWRTRMUIOCKN-UHFFFAOYSA-N

LogP

2.48

CAS DataBase Reference

100-53-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzenemethanethiol(100-53-8)

EPA Substance Registry System

Benzenemethanethiol (100-53-8)

Safety Information

Hazard Codes 

T,N

Risk Statements 

22-23-50/53

Safety Statements 

23-26-36/37/39-45-61-60

RIDADR 

2810

WGK Germany 

3

RTECS 

XT8650000

F 

10-13-23

Hazard Note 

Harmful/Lachrymator

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309090

Hazardous Substances Data

100-53-8(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Benzyl mercaptan Usage And Synthesis

Description

Benzyl mercaptan (C6H5CH2SH) is a kind of organosulfur compound. It is a commonly used alkaylthiol in the laboratory and is a naturally occurring compound. It has been found in boxwood and boost the smoky aroma in some kinds of wines. It is also naturally existed in coffee. It can be used as source of thiol functional group during the organic synthesis. In addition, it can also used as an odorant, synthetic flavor and as a bacteriostatic reagent. It is manufactured by the reaction of benzyl chloride and sodium hydrosulfide.

Chemical Properties

Cream to white, moist crystals; musty odor. Insoluble in water; soluble in alcohol or ether. There are three isomers with different boiling points.

Chemical Properties

Benzyl mercaptan has repulsive, garlic-like odor. It oxidizes in air to dibenzyl disulfide.

Occurrence

Reported found in coffee.

Uses

Intermediate, bacteriostat.

Uses

Benzyl mercaptan can be used as:

• A nucleophilic reagent in the cleavage of proanthocyanidins into their constitutive subunits.
• A reactant in the synthesis of dithiocarboxylic esters in the presence of phosphorus pentasulfide as a catalyst.
• A modifier to functionalize the surface of CNT for enhanced interaction with Pt-nanoparticles.

Definition

ChEBI: Benzyl thiol is a thiol that is toluene in which one of the methyl hydrogens has been replaced by a sulfanyl group. It has a role as a plant metabolite. It is a thiol and a member of benzenes. It derives from a hydride of a toluene.

Preparation

From benzyl chloride and potassium hydrosulfide.

Aroma threshold values

Detection: 0.19 to 2.6 ppb.

Taste threshold values

Taste characteristics at 15 ppm: leek, horseradish, cabbage, green, tomato and coffee.

Synthesis Reference(s)

Canadian Journal of Chemistry, 53, p. 1480, 1975 DOI: 10.1139/v75-205
Synthesis, p. 498, 1984 DOI: 10.1055/s-1984-30880

Hazard

Skin irritant.

Safety Profile

Poison by inhalation and intraperitoneal routes. Moderately toxic by ingestion. An eye irritant. Questionable carcinogen with experimental tumorigenic data. Flammable when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use foam, CO2, dry chemical, water spray, mist, fog. When heated to decomposition and on contact with acid or acid fumes it emits highly toxic fumes of SOx. See also SULFIDES and MERCAPTANS.

Purification Methods

Purify benzyl mercaptan via the mercury salt [see Kern J Am Chem Soc 75 1865 1953], which crystallises from *benzene as needles (m 121o), and then dissolve it in CHCl3. Pass H2S gas through the solution to regenerate the mercaptan. The HgS that precipitates is filtered off and washed thoroughly with CHCl3. The filtrate and washings are evaporated to remove CHCl3; then the residue is fractionally distilled under reduced pressure [Mackle & McClean, Trans Faraday Soc 58 895 1962]. [Beilstein 6 IV 2632.]

Benzyl mercaptan(100-53-8)Related Product Information

• Benzyl alcohol
• Benzyl benzoate
• Benzyl nicotinate
• α-Lipoic Acid
• Diethylstilbestrol
• PYRITHIOXIN
• Ethyl acetate
• 1,2-Ethanedithiol
• Sodium thiomethoxide
• Benzyl isocyanate
• 2-Ethylhexyl 10-ethyl-4-[[2-[(2-ethylhexyl)oxy]-2-oxoethyl]thio]-4-methyl-7-oxo-8-oxa-3,5-dithia-4-stannatetradecanoate
• METHYL MERCAPTAN
• 1-Dodecanethiol
• Ethanethiol
• Benzyl chloride
• PYRITHIOXIN DIHYDROCHLORIDE
• PROSULFOCARB
• Benzyl chloromethyl ether