2-Mesitylenesulfonyl chloride

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  • Identifiers

    CAS number
    773-64-8

    Molecular formula
    C9H11ClO2S

    SMILES
    CC1=CC(=C(C(=C1)C)S(=O)(=O)Cl)C

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fragrance
    Odorless 52.14%
    Roasted 25.61%
    Bitter 20.87%
    Cooked 20.21%
    Savory 19.28%
    Meaty 19.07%
    Burnt 18.97%
    Dry 18.11%
    Fatty 17.98%
    Sulfurous 17.39%

     

    Flavor
    Bitter 60.0%
    Odorless 24.16%
    Nitrile 21.21%
    Roasted peanuts 20.49%
    Bread crust 20.4%
    Taco 20.3%
    Very strong 20.0%
    Indole 19.85%
    Shellfish 19.84%
    Soybean 19.62%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    6.8 (neutral)

    Molecular weight
    218.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    289°C

    Flash point

    • 146.6 ˚C est.

  • Synonyms

    • 2-Mesitylenesulfonyl chloride
    • 773-64-8
    • Mesitylenesulfonyl chloride
    • Benzenesulfonyl chloride, 2,4,6-trimethyl-
    • EINECS 212-257-8
    • NSC 403295
    • BRN 1107601
    • DTXSID90228019
    • 3-11-00-00346 (Beilstein Handbook Reference)
    • RefChem:87788
    • DTXCID60150510
    • 2-Mesitylenesulfonyl chloride (8CI)
    • InChI=1/C9H11ClO2S/c1-6-4-7(2)9(8(3)5-6)13(10,11)12/h4-5H,1-3H
    • PVJZBZSCGJAWNG-UHFFFAOYSA-N
    • 2,4,6-Trimethylbenzenesulfonyl chloride
    • 2,4,6-trimethylbenzene-1-sulfonyl chloride
    • MESITYLSULFONYL CHLORIDE
    • MFCD00007434
    • 2-Mesitylenesulfonylchloride
    • Mesitylenesulphonyl chloride
    • 2,4,6-trimethylphenylsulfonyl chloride
    • NSC-403295
    • 2,4,6-Trimethyl-benzenesulfonyl chloride
    • Mesitylene-2-sulphonyl chloride
    • mesitylsulfonylchloride
    • mesitylenesulfonylchloride
    • 2-mesitylsulfonyl chloride
    • mesitylene sulfonyl chloride
    • SCHEMBL7608
    • 2-mesitylene sulfonyl chloride
    • 2-mesitylene sulphonyl chloride
    • 93TFV87MP5
    • WLN: WSGR B1 D1 F1
    • STR02217
    • 2-Mesitylenesulfonyl chloride, 99%
    • NSC403295
    • SBB066078
    • STL199175
    • 2,6-Trimethylbenzenesulfonyl chloride
    • chloro(2,4,6-trimethylphenyl)sulfone
    • 2,4,6-trimethylbenzenesulfonylchloride
    • AKOS000431085
    • 2,4,6-Trimethylbenzensulfonyl chloride
    • CS-W007703
    • SB21086
    • 2,6-(Trimethylbenzene)sulfonyl chloride
    • Benzenesulfonyl chloride,4,6-trimethyl-
    • 2,4,6-Trimethylbenzenesulphonyl chloride
    • 2,4,6trimethyl benzene sulphonyl chloride
    • 2,4,6 trimethyl benzene sulphonyl chloride
    • DB-000155
    • A9792
    • M0071
    • NS00037912
    • 2,4,6-trimethylbenzenesulphonic acid chloride
    • EN300-01722
    • F044837
    • Q21099516
    • F0808-2028
    • 773-64-8

  • Applications

    2-Mesitylenesulfonyl chloride is primarily a sulfonylating reagent used to install the bulky mesitylenesulfonyl group onto nucleophiles. In practice, it serves as a protecting group for amines in organic synthesis and peptide chemistry, enabling controlled sequence steps and straightforward deprotection. It also enables preparation of mesitylenesulfonamide derivatives by direct sulfonylation of amines, supporting intermediate synthesis in pharmaceuticals and fine chemicals. Additionally, it converts alcohols to mesitylenesulfonate esters, providing good leaving groups for subsequent substitutions in organic synthesis. In polymer and materials science, it is used to functionalize polymers by attaching sulfonyl or sulfonamide handles, enabling tailored properties or crosslinking. Overall, its applications span pharma and fine chemicals, basic organic synthesis, and materials research, with use governed by local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 127.89
    methanol 128.37
    isopropanol 77.11
    water 0.72
    ethyl acetate 578.23
    n-propanol 100.96
    acetone 714.76
    n-butanol 97.29
    acetonitrile 427.49
    DMF 1280.91
    toluene 308.99
    isobutanol 65.55
    1,4-dioxane 1153.74
    methyl acetate 551.34
    THF 2122.09
    2-butanone 505.44
    n-pentanol 59.93
    sec-butanol 74.0
    n-hexane 12.48
    ethylene glycol 47.41
    NMP 2040.39
    cyclohexane 47.55
    DMSO 779.45
    n-butyl acetate 263.51
    n-octanol 46.23
    chloroform 917.14
    n-propyl acetate 228.19
    acetic acid 301.41
    dichloromethane 1033.41
    cyclohexanone 1029.78
    propylene glycol 52.31
    isopropyl acetate 302.57
    DMAc 666.77
    2-ethoxyethanol 165.88
    isopentanol 74.22
    n-heptane 18.61
    ethyl formate 313.16
    1,2-dichloroethane 691.52
    n-hexanol 99.97
    2-methoxyethanol 414.39
    isobutyl acetate 121.89
    tetrachloromethane 124.38
    n-pentyl acetate 162.81
    transcutol 432.82
    n-heptanol 46.84
    ethylbenzene 86.6
    MIBK 242.54
    2-propoxyethanol 278.86
    tert-butanol 102.94
    MTBE 165.37
    2-butoxyethanol 115.83
    propionic acid 179.75
    o-xylene 129.29
    formic acid 130.97
    diethyl ether 293.88
    m-xylene 182.18
    p-xylene 105.42
    chlorobenzene 501.26
    dimethyl carbonate 412.62
    n-octane 6.4
    formamide 343.15
    cyclopentanone 1641.67
    2-pentanone 471.17
    anisole 322.19
    cyclopentyl methyl ether 744.44
    gamma-butyrolactone 1996.19
    1-methoxy-2-propanol 303.64
    pyridine 931.31
    3-pentanone 389.31
    furfural 1510.44
    n-dodecane 5.77
    diethylene glycol 209.71
    diisopropyl ether 86.64
    tert-amyl alcohol 83.28
    acetylacetone 822.84
    n-hexadecane 7.3
    acetophenone 303.37
    methyl propionate 528.24
    isopentyl acetate 196.41
    trichloroethylene 1706.15
    n-nonanol 47.99
    cyclohexanol 180.55
    benzyl alcohol 166.49
    2-ethylhexanol 69.92
    isooctanol 37.8
    dipropyl ether 145.93
    1,2-dichlorobenzene 450.02
    ethyl lactate 110.12
    propylene carbonate 882.24
    n-methylformamide 515.33
    2-pentanol 68.78
    n-pentane 15.92
    1-propoxy-2-propanol 182.24
    1-methoxy-2-propyl acetate 384.85
    2-(2-methoxypropoxy) propanol 147.14
    mesitylene 99.07
    ε-caprolactone 785.66
    p-cymene 67.06
    epichlorohydrin 1816.1
    1,1,1-trichloroethane 667.19
    2-aminoethanol 73.46
    morpholine-4-carbaldehyde 1443.1
    sulfolane 1877.42
    2,2,4-trimethylpentane 8.72
    2-methyltetrahydrofuran 1092.09
    n-hexyl acetate 215.58
    isooctane 8.66
    2-(2-butoxyethoxy)ethanol 185.77
    sec-butyl acetate 151.99
    tert-butyl acetate 354.95
    decalin 20.2
    glycerin 101.07
    diglyme 420.26
    acrylic acid 227.34
    isopropyl myristate 92.68
    n-butyric acid 243.16
    acetyl acetate 494.07
    di(2-ethylhexyl) phthalate 94.57
    ethyl propionate 249.83
    nitromethane 1266.86
    1,2-diethoxyethane 229.14
    benzonitrile 334.82
    trioctyl phosphate 67.87
    1-bromopropane 236.27
    gamma-valerolactone 1883.64
    n-decanol 38.13
    triethyl phosphate 113.33
    4-methyl-2-pentanol 44.55
    propionitrile 217.83
    vinylene carbonate 777.42
    1,1,2-trichlorotrifluoroethane 660.04
    DMS 360.12
    cumene 49.9
    2-octanol 35.34
    2-hexanone 207.64
    octyl acetate 119.69
    limonene 113.62
    1,2-dimethoxyethane 421.45
    ethyl orthosilicate 99.27
    tributyl phosphate 90.39
    diacetone alcohol 306.06
    N,N-dimethylaniline 158.32
    acrylonitrile 369.55
    aniline 313.92
    1,3-propanediol 122.93
    bromobenzene 568.25
    dibromomethane 551.57
    1,1,2,2-tetrachloroethane 931.47
    2-methyl-cyclohexyl acetate 188.6
    tetrabutyl urea 128.75
    diisobutyl methanol 46.51
    2-phenylethanol 205.02
    styrene 128.17
    dioctyl adipate 152.43
    dimethyl sulfate 712.36
    ethyl butyrate 210.81
    methyl lactate 228.52
    butyl lactate 111.12
    diethyl carbonate 149.78
    propanediol butyl ether 98.79
    triethyl orthoformate 141.96
    p-tert-butyltoluene 73.06
    methyl 4-tert-butylbenzoate 241.29
    morpholine 1094.06
    tert-butylamine 59.45
    n-dodecanol 30.25
    dimethoxymethane 811.85
    ethylene carbonate 562.66
    cyrene 313.61
    2-ethoxyethyl acetate 307.96
    2-ethylhexyl acetate 172.8
    1,2,4-trichlorobenzene 533.51
    4-methylpyridine 783.78
    dibutyl ether 82.02
    2,6-dimethyl-4-heptanol 46.51
    DEF 562.39
    dimethyl isosorbide 540.95
    tetrachloroethylene 520.49
    eugenol 195.67
    triacetin 284.71
    span 80 153.97
    1,4-butanediol 41.77
    1,1-dichloroethane 542.2
    2-methyl-1-pentanol 51.86
    methyl formate 599.95
    2-methyl-1-butanol 69.53
    n-decane 9.64
    butyronitrile 219.99
    3,7-dimethyl-1-octanol 50.15
    1-chlorooctane 53.81
    1-chlorotetradecane 24.17
    n-nonane 8.47
    undecane 7.32
    tert-butylcyclohexane 15.06
    cyclooctane 16.38
    cyclopentanol 259.49
    tetrahydropyran 826.84
    tert-amyl methyl ether 150.87
    2,5,8-trioxanonane 300.54
    1-hexene 45.89
    2-isopropoxyethanol 113.44
    2,2,2-trifluoroethanol 195.88
    methyl butyrate 290.88

    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