Benzyl mercaptan

CAS No. 100-53-8

Formula: C7H8S
Basic Info

Benzyl mercaptan is an organosulfur compound with the formula C6H5CH2SH. It is a common laboratory alkylthiol and occurs in trace amounts naturally. Condensed tannins can undergo acid-catalyzed cleavage in the presence of the nucleophilic benzyl mercaptan. Benzyl mercaptan has been identified in boxwood (Buxus sempervirens L.) and is known to contribute to the smoky aroma of certain wines. It also occurs naturally in coffee.
It is created by the reaction of benzyl chloride and sodium hydrosulfide.

Formula
C7H8S
Molecular Weight
124.203
Exact Mass
124.035
LogP
2.1164
PSA
38.8
Synonyms

Benzyl Mercaptan

Benzylthiol

Thiobenzyl Alcohol

benzenemethane-thiol

Benzenemethanethiol

phenylmethylmercaptan

FEMA 2147

phenyl methanethiol

toluene-a-thiol

usafex-1509

phenylmethylthiol

usafek-1509

Phenylmethanethiol

A-TOLUENETHIOL

α-Toluenethiol

Alpha-Toluenethiol

TOLUENETHIOL

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Properties
Appearance & Physical State
clear to light yellow liquid
Density
1.058
Boiling Point
195ºC (10 torr)
Melting Point
-29ºC
Flash Point
70ºC
Refractive Index
1.574-1.576
Stability
Stable. Combustible.
Vapor Density
>4 (vs air)
Vapor Pressure
0.591mmHg at 25°C
Safety Info
RTECS
XT8650000
Safety Statements
S23-S60-S61
WGK Germany
3
Risk Statements
R22; R23; R50/53
HS Code
2930909090
RIDADR
2810
Hazard Class
6.1
Packing Group
III
Caution Statement
P260; P284; P310
Hazard Codes
Hazard Declaration
Caution Statement
Spectrum
NMR Spectrum 1H NMR : 90 MHz in CDCl3
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IR Spectrum IR : liquid film
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Mass Spectrum Mass
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Analysis Methods
Kovats' RI, non-polar column, isothermal
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Column Shape
Packed
Active Phase(℃)
Apiezon M
Retention index
1104.
Temperature Control
130.
Method
isothermal
Comments
He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
Reference
Garbuzov, V.G.Misharina, T.A.Aerov, A.F.Golovnya, R.V.Gas chromatographic retention indices for sulphur(II)-containing organic substancesJ. Anal. Chem. USSR (Engl. Transl.)1985, 40, 4, 576-586.
Kovats' RI, non-polar column, isothermal
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Column Shape
Packed
Active Phase(℃)
Apiezon M
Retention index
1104.
Temperature Control
130.
Method
isothermal
Comments
Chromosorb W, AW/DMS; Column length: 2.1 m
Reference
Golovnya, R.V.Garbuzov, V.G.Aerov, A.F.Gas chromatographic characterization of sulfur-containing compounds. 5. Thiophene, furan, and benzene derivativesIzv. Akad. Nauk SSSR Ser. Khim.1978, 11, 2271-2274.
Van Den Dool and Kratz RI, polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
Supelcowax-10
Retention index
1615.
Temperature Control
Method
custom temperature program
Comments
30. m/0.25 mm/0.25 μm; Program: 40C(2min) => 40C/min => 60C(2min) => 5C/min => 240C
Reference
Majcher, M.A.Jelen, H.H.Effect of Cysteine and Cystine Addition on Sensory Profile and Potent Odorants of Extruded Potato SnacksJ. Agric. Food Chem.2007, 55, 14, 5754-5760.
Van Den Dool and Kratz RI, polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
Supelcowax-10
Retention index
1615.
Temperature Control
Method
custom temperature program
Comments
30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 40C/min => 60(2min)C => 5C/min => 240C
Reference
Majcher, M.A.Jelén, H.H.Identification of potent odorants formed during the preparation of extruded potato snacksJ. Agric. Food Chem.2005, 53, 16, 6432-6437.
Van Den Dool and Kratz RI, polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
DB-FFAP
Retention index
1626.
Temperature Control
Method
custom temperature program
Comments
30. m/0.32 mm/0.25 μm; Program: 35C(2min) => 6C/min => 180C => 10C/min => 240C (10min)
Reference
Huynh-Ba, T.Matthey-Doret, W.Fay, L.B.Rhlid, R.B.Generation of thiols by biotransformation of cysteine-aldehyde conjugates with Baker's yeastJ. Agric. Food Chem.2003, 51, 12, 3629-3635.
Toxicity
SKIN/EYE IRRITATION DATA
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Type of Test
Standard Draize test
Exposure Route
Administration into the eye
Species Observed
Rodent - rabbit
Dose/Duration
106 mg
Toxic Effects
--
Reference
American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 19,171,1958
ACUTE TOXICITY DATA
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Type of Test
LD50 - Lethal dose, 50 percent kill
Exposure Route
Oral
Species Observed
Rodent - rat
Dose/Duration
493 mg/kg
Toxic Effects
Behavioral--somnolence (general depressed activity)<br>Lungs, Thorax, or Respiration--respiratory depression<br>Behavioral--coma
Reference
American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 19,171,1958
ACUTE TOXICITY DATA
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Type of Test
LD50 - Lethal dose, 50 percent kill
Exposure Route
Intraperitoneal
Species Observed
Rodent - rat
Dose/Duration
373 mg/kg
Toxic Effects
Behavioral--somnolence (general depressed activity)<br>Lungs, Thorax, or Respiration--respiratory depression<br>Behavioral--coma
Reference
American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 19,171,1958

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