Methyl chloroformate

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  • Identifiers

    CAS number
    79-22-1

    Molecular formula
    C2H3ClO2

    SMILES
    COC(=O)Cl

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Fruity 62.87%
    Ethereal 58.6%
    Sharp 44.53%
    Pungent 40.32%
    Winey 40.15%
    Sour 37.32%
    Rummy 33.9%
    Odorless 33.61%
    Fermented 30.58%
    Apple 30.52%

     

    Flavor
    Pungent 35.05%
    Cheese 34.0%
    Sharp 33.41%
    Sour 33.39%
    Fruity 32.67%
    Odorless 30.59%
    Rancid 30.38%
    Acidic 29.36%
    Vinegar 28.86%
    Soy 23.43%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    5.33 (weak acid)

    Molecular weight
    94.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • less than -114 °F (USCG, 1999)
    • Less than -114 °F= less than -81 °C= less than 192 deg K
    • -61 °C

    Boiling point

    • 160 °F at 760 mmHg (EPA, 1998)
    • 71.0 °C
    • 71 °C

    Flash point

    • 7.26 ˚C est.
    • 54 °F (EPA, 1998)
    • 12 °C
    • 24.4 °C (Tag open cup), 17.8 °C (Tag closed cup)
    • 76 °F (open cup); 73 °F (closed cup)

    Solubility expt.

    • SOL IN CHLOROFORM, BENZENE, IN ALL PROPORTIONS IN ALCOHOL, ETHER
    • Solubility in water: poor

  • Synonyms

    • METHYL CHLOROFORMATE
    • 79-22-1
    • Methyl chlorocarbonate
    • methyl carbonochloridate
    • Chloroformic acid methyl ester
    • Methoxycarbonyl chloride
    • Metilcloroformiato
    • K-Stoff
    • Methylchloorformiaat
    • Carbonochloridic acid, methyl ester
    • RCRA waste number U156
    • Methyl chloridocarbonate
    • Formic acid, chloro-, methyl ester
    • Chloroformiate de methyle
    • Chlorocarbonic acid methyl ester
    • Chlorocarbonate de methyle
    • Methylchloorformiaat [Dutch]
    • Metilcloroformiato [Italian]
    • Chlorameisensaeure methylester
    • TL 438
    • HSDB 1116
    • Methylester kyseliny chlormravenci
    • Methylester kyseliny chloruhlicite
    • RC6VA8OB2N
    • Chloroformiate de methyle [French]
    • Chlorocarbonate de methyle [French]
    • EINECS 201-187-3
    • UN1238
    • Chlorameisensaeure methylester [German]
    • BRN 0605437
    • DTXSID0024185
    • Methylester kyseliny chlormravenci [Czech]
    • Methylester kyseliny chloruhlicite [Czech]
    • Carbonochloridic acid methyl ester
    • MFCD00000639
    • DTXCID004185
    • Chlorocarbonic acid, methyl ester
    • EC 201-187-3
    • METHYL CHLOROCARBONATE [MI]
    • METHYL CHLOROFORMATE [HSDB]
    • METHYLCHLOORFORMIAAT (DUTCH)
    • METILCLOROFORMIATO (ITALIAN)
    • CHLOROFORMIATE DE METHYLE (FRENCH)
    • CHLOROCARBONATE DE METHYLE (FRENCH)
    • CHLORAMEISENSAEURE METHYLESTER (GERMAN)
    • chloro(methoxy)methanone
    • METHYLCHLOROFORMATE
    • UNII-RC6VA8OB2N
    • RCRA waste no. U156
    • KStoff
    • methylchoroformate
    • Carbonochloridic acid, methylester
    • methy chloroformate
    • methyl chloroformat
    • methyl choroformate
    • ClCOOMe
    • MeOCOCl
    • methyl chioroformate
    • methyl-chloroformate
    • Chlorocarbonic Acid Methyl Ester; Methoxycarbonyl Chloride; Methyl Carbonochloridate; Methyl Chlorocarbonate; Methyl Chloroformate
    • methylchlorocarbonate
    • methyl chloroforrnate
    • ClCO2Me
    • methyl chloroform ate
    • methoxycarbonylchloride
    • methylcarbonochloridate
    • methylchloridocarbonate
    • CH3OCOCl
    • methyl carbonchloridate
    • MeOC(O)Cl
    • ClCO2CH3
    • chloro-(methoxy)methanone
    • Methyl chloridocarbonate #
    • Methyl chloroformate, 99%
    • chloro formic acid methyl ester
    • CHEMBL3182300
    • XMJHPCRAQCTCFT-UHFFFAOYSA-
    • Formic acid, chloro, methyl ester
    • Tox21_200841
    • BBL011482
    • STL146594
    • AKOS000121088
    • CHLOROFORMIC ACID, METHYL ESTER
    • UN 1238
    • CAS-79-22-1
    • NCGC00248847-01
    • NCGC00258395-01
    • BP-31038
    • Methyl chloroformate [UN1238] [Poison]
    • NS00002965
    • InChI=1/C2H3ClO2/c1-5-2(3)4/h1H3
    • Q419678
    • 201-187-3

  • Applications

    Methyl chloroformate (CAS number: 79-22-1) is widely used as an acylating reagent in organic synthesis, converting amines to methyl carbamates for protection and as pharmaceutical intermediates; it also reacts with alcohols and phenols to form methyl esters or methyl carbonates, enabling the preparation of protected monomers and specialty chemicals; in analytical chemistry it serves as a derivatizing reagent for GC-MS and LC analyses to convert amines, acids, and alcohols to volatile derivatives; in the coatings, adhesives, and polymer sectors it is used to introduce urethane- or carbonate-functional groups into intermediates and monomers for improved performance of coatings and sealants; it is also employed in process chemistry to rapidly generate methyl chloroformate derivatives of a broad range of substrates.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 243.77
    methanol 329.34
    isopropanol 206.08
    water 57.66
    ethyl acetate 153.32
    n-propanol 157.58
    acetone 449.57
    n-butanol 142.06
    acetonitrile 287.48
    DMF 953.97
    toluene 57.17
    isobutanol 129.84
    1,4-dioxane 293.78
    methyl acetate 234.8
    THF 309.7
    2-butanone 249.39
    n-pentanol 103.79
    sec-butanol 173.82
    n-hexane 14.12
    ethylene glycol 109.92
    NMP 798.02
    cyclohexane 19.86
    DMSO 967.88
    n-butyl acetate 65.92
    n-octanol 54.46
    chloroform 259.52
    n-propyl acetate 92.17
    acetic acid 494.49
    dichloromethane 332.43
    cyclohexanone 236.81
    propylene glycol 84.18
    isopropyl acetate 100.82
    DMAc 816.52
    2-ethoxyethanol 244.73
    isopentanol 137.94
    n-heptane 12.23
    ethyl formate 167.02
    1,2-dichloroethane 230.47
    n-hexanol 62.94
    2-methoxyethanol 402.78
    isobutyl acetate 46.41
    tetrachloromethane 74.87
    n-pentyl acetate 62.38
    transcutol 277.85
    n-heptanol 52.12
    ethylbenzene 40.32
    MIBK 116.72
    2-propoxyethanol 127.45
    tert-butanol 323.32
    MTBE 213.38
    2-butoxyethanol 101.5
    propionic acid 173.88
    o-xylene 74.41
    formic acid 427.48
    diethyl ether 156.32
    m-xylene 50.36
    p-xylene 65.52
    chlorobenzene 81.97
    dimethyl carbonate 117.24
    n-octane 6.95
    formamide 712.41
    cyclopentanone 305.24
    2-pentanone 180.24
    anisole 140.86
    cyclopentyl methyl ether 152.1
    gamma-butyrolactone 315.73
    1-methoxy-2-propanol 274.67
    pyridine 237.49
    3-pentanone 147.42
    furfural 417.25
    n-dodecane 5.93
    diethylene glycol 139.27
    diisopropyl ether 51.11
    tert-amyl alcohol 269.57
    acetylacetone 243.36
    n-hexadecane 6.58
    acetophenone 153.29
    methyl propionate 160.27
    isopentyl acetate 66.05
    trichloroethylene 457.65
    n-nonanol 49.23
    cyclohexanol 129.74
    benzyl alcohol 116.21
    2-ethylhexanol 46.25
    isooctanol 47.9
    dipropyl ether 52.54
    1,2-dichlorobenzene 95.14
    ethyl lactate 61.34
    propylene carbonate 150.86
    n-methylformamide 458.99
    2-pentanol 115.59
    n-pentane 21.76
    1-propoxy-2-propanol 88.04
    1-methoxy-2-propyl acetate 86.96
    2-(2-methoxypropoxy) propanol 118.5
    mesitylene 42.83
    ε-caprolactone 184.92
    p-cymene 34.43
    epichlorohydrin 336.1
    1,1,1-trichloroethane 200.56
    2-aminoethanol 159.78
    morpholine-4-carbaldehyde 522.24
    sulfolane 505.95
    2,2,4-trimethylpentane 17.83
    2-methyltetrahydrofuran 254.01
    n-hexyl acetate 77.3
    isooctane 10.66
    2-(2-butoxyethoxy)ethanol 129.29
    sec-butyl acetate 63.87
    tert-butyl acetate 135.44
    decalin 13.05
    glycerin 149.96
    diglyme 280.91
    acrylic acid 214.36
    isopropyl myristate 38.37
    n-butyric acid 171.81
    acetyl acetate 119.06
    di(2-ethylhexyl) phthalate 45.97
    ethyl propionate 86.08
    nitromethane 866.75
    1,2-diethoxyethane 101.7
    benzonitrile 121.32
    trioctyl phosphate 32.86
    1-bromopropane 102.72
    gamma-valerolactone 397.4
    n-decanol 38.08
    triethyl phosphate 49.59
    4-methyl-2-pentanol 73.46
    propionitrile 138.86
    vinylene carbonate 150.06
    1,1,2-trichlorotrifluoroethane 329.65
    DMS 73.8
    cumene 36.86
    2-octanol 45.33
    2-hexanone 113.26
    octyl acetate 47.82
    limonene 52.96
    1,2-dimethoxyethane 361.03
    ethyl orthosilicate 47.44
    tributyl phosphate 35.14
    diacetone alcohol 209.01
    N,N-dimethylaniline 143.52
    acrylonitrile 212.39
    aniline 128.18
    1,3-propanediol 205.25
    bromobenzene 70.03
    dibromomethane 184.04
    1,1,2,2-tetrachloroethane 315.7
    2-methyl-cyclohexyl acetate 64.32
    tetrabutyl urea 61.15
    diisobutyl methanol 39.62
    2-phenylethanol 79.59
    styrene 52.57
    dioctyl adipate 60.29
    dimethyl sulfate 267.42
    ethyl butyrate 67.69
    methyl lactate 108.02
    butyl lactate 54.51
    diethyl carbonate 51.12
    propanediol butyl ether 98.27
    triethyl orthoformate 52.18
    p-tert-butyltoluene 36.8
    methyl 4-tert-butylbenzoate 122.28
    morpholine 334.48
    tert-butylamine 198.5
    n-dodecanol 30.19
    dimethoxymethane 339.91
    ethylene carbonate 108.24
    cyrene 157.08
    2-ethoxyethyl acetate 88.42
    2-ethylhexyl acetate 51.11
    1,2,4-trichlorobenzene 126.07
    4-methylpyridine 248.65
    dibutyl ether 47.81
    2,6-dimethyl-4-heptanol 39.62
    DEF 321.62
    dimethyl isosorbide 167.9
    tetrachloroethylene 262.32
    eugenol 117.28
    triacetin 100.03
    span 80 89.13
    1,4-butanediol 90.96
    1,1-dichloroethane 197.35
    2-methyl-1-pentanol 105.99
    methyl formate 347.65
    2-methyl-1-butanol 133.09
    n-decane 9.21
    butyronitrile 140.48
    3,7-dimethyl-1-octanol 56.05
    1-chlorooctane 30.74
    1-chlorotetradecane 14.77
    n-nonane 8.93
    undecane 7.15
    tert-butylcyclohexane 13.35
    cyclooctane 8.93
    cyclopentanol 148.97
    tetrahydropyran 175.51
    tert-amyl methyl ether 176.84
    2,5,8-trioxanonane 210.19
    1-hexene 41.96
    2-isopropoxyethanol 151.92
    2,2,2-trifluoroethanol 264.25
    methyl butyrate 133.36

    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