Allyl chloroformate

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  • Identifiers

    CAS number
    2937-50-0

    Molecular formula
    C4H5ClO2

    SMILES
    C=CCOC(=O)Cl

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Fruity 89.42%
    Ethereal 42.58%
    Sharp 41.5%
    Pungent 39.63%
    Apple 35.7%
    Winey 35.63%
    Pineapple 34.95%
    Tropical 34.17%
    Sour 32.96%
    Green 32.52%

     

    Flavor
    Odorless 33.88%
    Sour 30.53%
    Pungent 26.74%
    Acidic 25.89%
    Fruity 22.82%
    Sharp 20.8%
    Acetoin 20.73%
    Soy 20.44%
    Roquefort cheese 20.31%
    Formyl 20.11%

     

    Odor impact est.
    Medium

    Odor threshold

    • 1.4 PPM.

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    6.76 (neutral)

    Molecular weight
    120.53 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -112 °F (USCG, 1999)
    • Freezing point: -112 °F = -80 °C = 193 K

    Boiling point

    • 235 °F at 760 mmHg (USCG, 1999)
    • 109.5 °C

    Flash point

    • 26.09 ˚C est.
    • 88 °F (USCG, 1999)
    • 31 °C
    • 88 °F (31 °C) (Closed Cup)
    • Flash point: 27.8 °C (Tag open cup), 31.1 °C (Tag closed cup)

    Solubility expt.

    • Insoluble in water

  • Synonyms

    • ALLYL CHLOROFORMATE
    • 2937-50-0
    • Chloroformic acid allyl ester
    • Allyl chlorocarbonate
    • allylchloroformate
    • allyl carbonochloridate
    • 2-Propenyl chloroformate
    • Carbonochloridic acid, 2-propenyl ester
    • Carbonochloridic acid, 2-propen-1-yl ester
    • Formic acid, chloro-, allyl ester
    • prop-2-enyl carbonochloridate
    • HSDB 621
    • allyloxycarbonyl chloride
    • Allylester kyseliny chlormravenci
    • EINECS 220-916-6
    • UN1722
    • BRN 0773915
    • Allylester kyseliny chlormravenci [Czech]
    • Allyl chloridocarbonate
    • MFCD00000648
    • 7672CAR559
    • DTXSID2051972
    • prop-2-en-1-yl carbonochloridate
    • 2-PROPEN-1-YL CHLOROFORMATE
    • 2-PROPENYL CHLOROFORMATE [HSDB]
    • 560088-71-3
    • ALLYL CHLOROFORMATE (ALLYL CHLOROCARBONATE)
    • ALLYL CHLOROFORMATE {ALLYL CHLOROCARBONATE}
    • allylchoroformate
    • AllyChloroformate
    • aliylchloroformate
    • UNII-7672CAR559
    • Alloc-Cl
    • allyl chlorformate
    • Ally Chloroformate
    • 2Propenyl chloroformate
    • Allyl chloridocarbonate #
    • prop-2-enyl chloroformate
    • Allyl chloroformate, 97%
    • SCHEMBL37486
    • DTXCID5030535
    • CAEWJEXPFKNBQL-UHFFFAOYSA-
    • Formic acid, chloro, allyl ester
    • chloro(prop-2-en-1-yloxy)methanone
    • BBL011109
    • STK802356
    • AKOS000121050
    • Carbonochloridic acid, 2propenyl ester
    • FS-4334
    • UN 1722
    • Allyl chloroformate [UN1722] [Poison]
    • A1268
    • NS00028678
    • EN300-21727
    • D87847
    • Q27266461
    • InChI=1/C4H5ClO2/c1-2-3-7-4(5)6/h2H,1,3H2
    • 220-916-6

  • Applications

    Allyl chloroformate is primarily used in organic synthesis as a reactive acylating agent to install allyl carbonate and allyl carbamate (Alloc) protecting groups on amines and alcohols, making it a common intermediate in pharmaceutical and specialty chemical synthesis. It also serves to introduce allyl carbonate or carbamate functionalities into molecules, enabling selective deprotection by palladium-catalyzed methods or hydrogenolysis in multi-step routes. In polymer and materials chemistry, it is used to graft protected or crosslinkable allyl carbonate or carbamate groups onto monomers or oligomers, supporting post-polymerization modification, curing in coatings and adhesives, and the preparation of specialty polymers. Its applications are typical of process-level chemical synthesis and materials formulation, and use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 230.01
    methanol 270.64
    isopropanol 182.54
    water 1.14
    ethyl acetate 245.14
    n-propanol 163.16
    acetone 554.15
    n-butanol 176.4
    acetonitrile 305.08
    DMF 1553.02
    toluene 140.08
    isobutanol 131.53
    1,4-dioxane 306.62
    methyl acetate 335.95
    THF 566.56
    2-butanone 406.49
    n-pentanol 153.53
    sec-butanol 198.31
    n-hexane 25.61
    ethylene glycol 77.6
    NMP 925.1
    cyclohexane 24.88
    DMSO 1045.44
    n-butyl acetate 201.87
    n-octanol 123.41
    chloroform 266.09
    n-propyl acetate 189.4
    acetic acid 292.66
    dichloromethane 328.25
    cyclohexanone 362.24
    propylene glycol 87.47
    isopropyl acetate 144.97
    DMAc 1171.86
    2-ethoxyethanol 268.49
    isopentanol 172.84
    n-heptane 21.5
    ethyl formate 210.45
    1,2-dichloroethane 298.84
    n-hexanol 150.34
    2-methoxyethanol 437.95
    isobutyl acetate 106.7
    tetrachloromethane 36.47
    n-pentyl acetate 152.94
    transcutol 739.13
    n-heptanol 91.09
    ethylbenzene 108.21
    MIBK 178.64
    2-propoxyethanol 251.77
    tert-butanol 257.51
    MTBE 277.5
    2-butoxyethanol 181.74
    propionic acid 171.07
    o-xylene 131.41
    formic acid 118.34
    diethyl ether 201.9
    m-xylene 117.64
    p-xylene 135.76
    chlorobenzene 171.14
    dimethyl carbonate 143.91
    n-octane 13.64
    formamide 203.03
    cyclopentanone 472.09
    2-pentanone 295.58
    anisole 237.54
    cyclopentyl methyl ether 242.4
    gamma-butyrolactone 445.61
    1-methoxy-2-propanol 340.09
    pyridine 354.83
    3-pentanone 220.31
    furfural 538.34
    n-dodecane 15.41
    diethylene glycol 215.11
    diisopropyl ether 71.78
    tert-amyl alcohol 280.95
    acetylacetone 336.65
    n-hexadecane 16.8
    acetophenone 259.67
    methyl propionate 247.58
    isopentyl acetate 173.03
    trichloroethylene 551.37
    n-nonanol 103.8
    cyclohexanol 155.41
    benzyl alcohol 179.38
    2-ethylhexanol 110.22
    isooctanol 78.66
    dipropyl ether 102.2
    1,2-dichlorobenzene 178.75
    ethyl lactate 107.48
    propylene carbonate 242.14
    n-methylformamide 409.35
    2-pentanol 149.83
    n-pentane 26.79
    1-propoxy-2-propanol 203.12
    1-methoxy-2-propyl acetate 191.29
    2-(2-methoxypropoxy) propanol 234.65
    mesitylene 80.26
    ε-caprolactone 308.22
    p-cymene 68.94
    epichlorohydrin 494.13
    1,1,1-trichloroethane 230.92
    2-aminoethanol 119.84
    morpholine-4-carbaldehyde 653.53
    sulfolane 606.63
    2,2,4-trimethylpentane 23.75
    2-methyltetrahydrofuran 383.38
    n-hexyl acetate 224.12
    isooctane 16.21
    2-(2-butoxyethoxy)ethanol 292.04
    sec-butyl acetate 121.54
    tert-butyl acetate 184.67
    decalin 26.22
    glycerin 132.14
    diglyme 527.77
    acrylic acid 186.69
    isopropyl myristate 88.05
    n-butyric acid 202.72
    acetyl acetate 147.42
    di(2-ethylhexyl) phthalate 94.18
    ethyl propionate 160.53
    nitromethane 635.23
    1,2-diethoxyethane 235.79
    benzonitrile 236.34
    trioctyl phosphate 68.23
    1-bromopropane 171.66
    gamma-valerolactone 527.9
    n-decanol 81.58
    triethyl phosphate 77.54
    4-methyl-2-pentanol 93.85
    propionitrile 187.77
    vinylene carbonate 245.22
    1,1,2-trichlorotrifluoroethane 353.58
    DMS 179.94
    cumene 74.99
    2-octanol 85.16
    2-hexanone 230.8
    octyl acetate 116.82
    limonene 103.02
    1,2-dimethoxyethane 530.49
    ethyl orthosilicate 73.39
    tributyl phosphate 85.27
    diacetone alcohol 270.3
    N,N-dimethylaniline 208.49
    acrylonitrile 285.01
    aniline 158.1
    1,3-propanediol 168.49
    bromobenzene 175.76
    dibromomethane 221.49
    1,1,2,2-tetrachloroethane 401.28
    2-methyl-cyclohexyl acetate 125.59
    tetrabutyl urea 146.68
    diisobutyl methanol 75.99
    2-phenylethanol 157.61
    styrene 137.9
    dioctyl adipate 130.89
    dimethyl sulfate 298.01
    ethyl butyrate 140.68
    methyl lactate 155.65
    butyl lactate 129.41
    diethyl carbonate 98.74
    propanediol butyl ether 223.85
    triethyl orthoformate 97.64
    p-tert-butyltoluene 71.31
    methyl 4-tert-butylbenzoate 194.44
    morpholine 375.53
    tert-butylamine 155.65
    n-dodecanol 66.97
    dimethoxymethane 425.04
    ethylene carbonate 159.06
    cyrene 213.21
    2-ethoxyethyl acetate 206.68
    2-ethylhexyl acetate 137.95
    1,2,4-trichlorobenzene 222.45
    4-methylpyridine 401.33
    dibutyl ether 137.83
    2,6-dimethyl-4-heptanol 75.99
    DEF 480.83
    dimethyl isosorbide 299.43
    tetrachloroethylene 243.28
    eugenol 223.46
    triacetin 198.24
    span 80 175.6
    1,4-butanediol 90.16
    1,1-dichloroethane 246.2
    2-methyl-1-pentanol 162.93
    methyl formate 340.69
    2-methyl-1-butanol 171.53
    n-decane 21.41
    butyronitrile 200.62
    3,7-dimethyl-1-octanol 122.71
    1-chlorooctane 80.49
    1-chlorotetradecane 39.6
    n-nonane 20.7
    undecane 17.71
    tert-butylcyclohexane 26.38
    cyclooctane 13.31
    cyclopentanol 161.3
    tetrahydropyran 262.92
    tert-amyl methyl ether 258.84
    2,5,8-trioxanonane 375.97
    1-hexene 95.65
    2-isopropoxyethanol 188.13
    2,2,2-trifluoroethanol 101.26
    methyl butyrate 239.05

    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