Benzyl mercaptan

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  • Identifiers

    CAS number
    100-53-8

    Molecular formula
    C7H8S

    SMILES
    C1=CC=C(C=C1)CS

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1075.0

  • Odor profile

    Sulfurous 92.63%
    Meaty 64.86%
    Garlic 64.85%
    Burnt 59.67%
    Onion 59.46%
    Roasted 56.97%
    Alliaceous 56.39%
    Coffee 54.83%
    Savory 48.79%
    Vegetable 47.52%

    Scent© AI

    Odor threshold>

    • Odor Threshold Low: 0.0026 [mmHg]. Odor Threshold High: 0.04 [mmHg]. Odor threshold from CHEMINFO
    • Its odor threshold is 2.6 ppb; human nasal irritation starts at 4.5 ppm and eye irritation at 7.5 ppm.
    • Threshold of odor detection... 0.03 mg/cu m for benzyl mercaptan... .

  • Properties

    XLogP3-AA
    2.4

    Molecular weight
    124.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • -30 °C

    Boiling point

    • 194-195 °C
    • 194.00 to 195.00 °C. @ 760.00 mm Hg

    Flash point est.
    68.74 ˚C

    Flash point expt.

    • 158 °F (70 °C)(Closed cup)

    Solubility expt.

    • Slightly soluble in carbon tetrachloride; soluble in carbon disulfide; very soluble in ethanol and ether
    • insoluble in water; soluble in oils
    • 1 ml in 1 ml 95% alcohol (in ethanol)

  • Synonyms

    • BENZYL MERCAPTAN
    • Phenylmethanethiol
    • Benzenemethanethiol
    • 100-53-8
    • Benzylthiol
    • Thiobenzyl alcohol
    • alpha-Toluenethiol
    • Toluene-alpha-thiol
    • Benzylhydrosulfide
    • Benzylmercaptan
    • alpha-Mercaptotoluene
    • Phenylmethyl mercaptan
    • Benzyl hydrosulfide
    • Methanethiol, phenyl-
    • benzyl thiol
    • (Mercaptomethyl)benzene
    • alpha-Toluolthiol
    • alpha-Tolyl mercaptan
    • phenyl-methanethiol
    • Toluene, alpha-mercapto-
    • .alpha.-Toluenethiol
    • a-toluenethiol
    • USAF ex-1509
    • .alpha.-Tolyl mercaptan
    • FEMA No. 2147
    • .alpha.-Toluolthiol
    • benzylsulfane
    • NSC 41897
    • CCRIS 9101
    • HSDB 2105
    • UNII-OS34A21OBZ
    • EINECS 202-862-5
    • OS34A21OBZ
    • (Thiomethyl)benzene
    • BRN 0605864
    • DODEOYL BENZYL MERCAPTAN
    • a-Toluenethiol, 8CI
    • DTXSID6026664
    • alpha-Mercapto-Toluene
    • AI3-22955
    • .alpha.-Mercaptotoluene
    • Benzenemethanethiol, 9CI
    • NSC-41897
    • TOLUENE-.ALPHA.-THIOL
    • DTXCID206664
    • BENZYL MERCAPTAN [FHFI]
    • BENZYL MERCAPTAN [HSDB]
    • THIOBENZYL ALCOHOL [MI]
    • CHEMBL1224557
    • FEMA 2147
    • CHEBI:137674
    • BENZYL MERCAPTAN [USP-RS]
    • 4-06-00-02632 (Beilstein Handbook Reference)
    • 16528-58-8
    • BENZYL MERCAPTAN (USP-RS)
    • benzyl-MERCAPTAN
    • benzylmercaptane
    • alphaToluolthiol
    • a-Toluolthiol
    • toluene-a-thiol
    • alphaToluenethiol
    • a-Mercaptotoluene
    • a-Tolyl mercaptan
    • alpha -toluolthiol
    • phenyl methanethiol
    • alphaMercaptotoluene
    • BnSH
    • alpha -toluenethiol
    • benzyl hydrosulphide
    • alphaTolyl mercaptan
    • Methanethiol, phenyl
    • Toluene-I+--thiol
    • MFCD00004867
    • alpha -mercaptotoluene
    • Toluene, alphamercapto
    • alpha -tolyl mercaptan
    • Benzyl mercaptan, 99%
    • Usaf ek-1509
    • SCHEMBL205
    • Benzyl Mercaptan - 96%
    • WLN: SH1R
    • Benzyl mercaptan, 99%, FG
    • NSC41897
    • Tox21_200129
    • BDBM50325566
    • Benzyl mercaptan, analytical standard
    • NSC229567
    • STL299685
    • Thiomethyl resin (200-400 mesh)
    • AKOS000120383
    • AT29982
    • FB05260
    • NSC-229567
    • NCGC00248534-01
    • NCGC00257683-01
    • CAS-100-53-8
    • FT111714
    • Benzyl mercaptan, purum, >=99.0% (GC)
    • DB-003602
    • NS00020907
    • T0287
    • EN300-16494
    • A800227
    • Q3740628
    • Z55948218
    • F0001-0020
    • Benzyl mercaptan, United States Pharmacopeia (USP) Reference Standard
    • SDQ

  • Applications

    Benzyl mercaptan (C6H5CH2SH, CAS 100-53-8) is an aromatic thiol with a pungent odor that is widely used in organic synthesis as a protecting and dehalogenating reagent, a radical chain-transfer agent in polymer chemistry, a precursor for benzyl sulfide derivatives in pharmaceuticals, agrochemicals and surfactants, a sulfur-containing tracer in mechanistic studies, a trace-level flavor modifier in food and beverages, a garlic-like fragrance component, and a corrosion inhibitor through formation of sulfur-rich protective films on metal surfaces.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 295.39
    methanol 284.52
    isopropanol 234.6
    water 0.6
    ethyl acetate 405.41
    n-propanol 260.02
    acetone 672.77
    n-butanol 252.5
    acetonitrile 405.94
    DMF 680.56
    toluene 295.18
    isobutanol 193.94
    1,4-dioxane 1229.46
    methyl acetate 430.72
    THF 1011.4
    2-butanone 481.33
    n-pentanol 230.07
    sec-butanol 211.3
    n-hexane 116.87
    ethylene glycol 72.72
    NMP 630.58
    cyclohexane 127.41
    DMSO 921.77
    n-butyl acetate 433.01
    n-octanol 157.58
    chloroform 1029.76
    n-propyl acetate 356.12
    acetic acid 261.39
    dichloromethane 948.72
    cyclohexanone 750.46
    propylene glycol 81.84
    isopropyl acetate 244.09
    DMAc 419.52
    2-ethoxyethanol 338.51
    isopentanol 215.37
    n-heptane 118.0
    ethyl formate 243.79
    1,2-dichloroethane 678.85
    n-hexanol 316.16
    2-methoxyethanol 444.83
    isobutyl acetate 262.12
    tetrachloromethane 249.86
    n-pentyl acetate 219.01
    transcutol 1063.96
    n-heptanol 154.01
    ethylbenzene 158.21
    MIBK 285.95
    2-propoxyethanol 467.88
    tert-butanol 292.78
    MTBE 319.22
    2-butoxyethanol 263.99
    propionic acid 241.82
    o-xylene 147.38
    formic acid 61.62
    diethyl ether 530.77
    m-xylene 171.87
    p-xylene 187.73
    chlorobenzene 354.45
    dimethyl carbonate 175.76
    n-octane 46.75
    formamide 111.02
    cyclopentanone 801.6
    2-pentanone 421.61
    anisole 335.08
    cyclopentyl methyl ether 485.22
    gamma-butyrolactone 714.3
    1-methoxy-2-propanol 343.75
    pyridine 737.35
    3-pentanone 329.08
    furfural 610.53
    n-dodecane 33.51
    diethylene glycol 308.54
    diisopropyl ether 153.48
    tert-amyl alcohol 223.44
    acetylacetone 469.38
    n-hexadecane 37.63
    acetophenone 283.32
    methyl propionate 315.22
    isopentyl acetate 299.85
    trichloroethylene 1001.31
    n-nonanol 142.32
    cyclohexanol 246.63
    benzyl alcohol 205.18
    2-ethylhexanol 209.95
    isooctanol 135.68
    dipropyl ether 373.29
    1,2-dichlorobenzene 284.33
    ethyl lactate 136.52
    propylene carbonate 379.89
    n-methylformamide 269.05
    2-pentanol 186.98
    n-pentane 85.01
    1-propoxy-2-propanol 319.3
    1-methoxy-2-propyl acetate 296.79
    2-(2-methoxypropoxy) propanol 227.96
    mesitylene 122.92
    ε-caprolactone 534.49
    p-cymene 108.19
    epichlorohydrin 776.55
    1,1,1-trichloroethane 614.65
    2-aminoethanol 127.03
    morpholine-4-carbaldehyde 787.67
    sulfolane 864.04
    2,2,4-trimethylpentane 38.43
    2-methyltetrahydrofuran 691.23
    n-hexyl acetate 280.17
    isooctane 41.83
    2-(2-butoxyethoxy)ethanol 337.11
    sec-butyl acetate 211.26
    tert-butyl acetate 282.97
    decalin 70.68
    glycerin 133.17
    diglyme 676.56
    acrylic acid 201.06
    isopropyl myristate 141.34
    n-butyric acid 316.37
    acetyl acetate 258.17
    di(2-ethylhexyl) phthalate 103.96
    ethyl propionate 261.09
    nitromethane 531.16
    1,2-diethoxyethane 465.76
    benzonitrile 283.59
    trioctyl phosphate 90.78
    1-bromopropane 442.01
    gamma-valerolactone 868.42
    n-decanol 115.05
    triethyl phosphate 121.97
    4-methyl-2-pentanol 129.76
    propionitrile 305.8
    vinylene carbonate 347.68
    1,1,2-trichlorotrifluoroethane 433.03
    DMS 230.88
    cumene 113.05
    2-octanol 110.02
    2-hexanone 399.06
    octyl acetate 161.86
    limonene 162.05
    1,2-dimethoxyethane 691.26
    ethyl orthosilicate 121.3
    tributyl phosphate 104.11
    diacetone alcohol 286.27
    N,N-dimethylaniline 212.45
    acrylonitrile 348.45
    aniline 241.53
    1,3-propanediol 195.34
    bromobenzene 420.11
    dibromomethane 702.98
    1,1,2,2-tetrachloroethane 744.3
    2-methyl-cyclohexyl acetate 205.41
    tetrabutyl urea 143.4
    diisobutyl methanol 133.1
    2-phenylethanol 226.48
    styrene 218.03
    dioctyl adipate 167.93
    dimethyl sulfate 281.02
    ethyl butyrate 287.58
    methyl lactate 144.24
    butyl lactate 150.57
    diethyl carbonate 172.2
    propanediol butyl ether 195.12
    triethyl orthoformate 178.01
    p-tert-butyltoluene 106.04
    methyl 4-tert-butylbenzoate 207.91
    morpholine 954.77
    tert-butylamine 191.79
    n-dodecanol 98.22
    dimethoxymethane 507.2
    ethylene carbonate 316.33
    cyrene 224.0
    2-ethoxyethyl acetate 280.41
    2-ethylhexyl acetate 258.19
    1,2,4-trichlorobenzene 320.91
    4-methylpyridine 553.29
    dibutyl ether 260.38
    2,6-dimethyl-4-heptanol 133.1
    DEF 429.1
    dimethyl isosorbide 376.6
    tetrachloroethylene 553.04
    eugenol 213.19
    triacetin 246.43
    span 80 207.03
    1,4-butanediol 108.5
    1,1-dichloroethane 597.79
    2-methyl-1-pentanol 197.61
    methyl formate 231.49
    2-methyl-1-butanol 189.79
    n-decane 53.09
    butyronitrile 296.25
    3,7-dimethyl-1-octanol 152.92
    1-chlorooctane 156.02
    1-chlorotetradecane 70.67
    n-nonane 56.95
    undecane 40.5
    tert-butylcyclohexane 72.41
    cyclooctane 56.41
    cyclopentanol 261.38
    tetrahydropyran 853.13
    tert-amyl methyl ether 216.39
    2,5,8-trioxanonane 440.17
    1-hexene 279.94
    2-isopropoxyethanol 272.48
    2,2,2-trifluoroethanol 104.86
    methyl butyrate 350.11

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Petiveria alliaceae (Brazil) flower Petiveria alliaceae L., fam. Phytolaccaceae 20.3%