Benzyl chloroformate

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  • Identifiers

    CAS number
    501-53-1

    Molecular formula
    C8H7ClO2

    SMILES
    C1=CC=C(C=C1)COC(=O)Cl

    Safety labels

    Corrosive
    Corrosive

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 65.01%
    Balsamic 54.12%
    Fruity 49.92%
    Sweet 44.84%
    Honey 43.1%
    Rose 33.81%
    Winey 29.51%
    Grape 29.22%
    Herbal 28.18%
    Phenolic 28.01%

     

    Flavor
    Sweet 79.25%
    Fruity 64.79%
    Balsam 47.9%
    Floral 46.95%
    Honey 36.23%
    Strawberry 35.03%
    Grape 34.65%
    Powdery 33.32%
    Balsamic 32.53%
    Cherry 31.55%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    6.07 (neutral)

    Molecular weight
    170.59 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 0 °C

    Boiling point

    • 306 °F at 760 mmHg (decomposes) (USCG, 1999)
    • 152 °C AT 760 MM HG

    Flash point

    • 96.03 ˚C est.
    • 227 °F Vigorous decomposition occurs at these temperatures; thus these values are anomalous due to the effect of the decomp. products (benzyl chloride and CO2). (USCG, 1999)
    • [HSDB] 80 °C
    • 176 °F OC; 227 °F CC
    • 80.0 °C c.c.

    Solubility expt.

    • SOL IN ETHER, ACETONE, BENZENE
    • Solubility in water: reaction

  • Synonyms

    • BENZYL CHLOROFORMATE
    • 501-53-1
    • Benzyl carbonochloridate
    • Carbobenzoxy chloride
    • Benzyl chlorocarbonate
    • Cbz chloride
    • Benzyloxycarbonyl chloride
    • Carbobenzyloxy chloride
    • Carbonochloridic acid, phenylmethyl ester
    • Benzylcarbonyl chloride
    • Cbz-Cl
    • Chloroformic acid, benzyl ester
    • Benzylcarbonochloridate
    • Z-Cl
    • Formic acid, chloro-, benzyl ester
    • NSC 83466
    • Chloroformic Acid Benzyl Ester
    • CCRIS 2599
    • HSDB 364
    • phenylmethyl chloroformate
    • Z-chloride
    • (benzyloxy)carbonyl chloride
    • EINECS 207-925-0
    • UN1739
    • UNII-170BP0DD31
    • carbonochloridic acid phenylmethyl ester
    • DTXSID9027158
    • MFCD00000640
    • NSC-83466
    • DTXCID607158
    • CARBOBENZOXY CHLORIDE [MI]
    • EC 207-925-0
    • 170BP0DD31
    • BENZYL CHLOROFORMATE [HSDB]
    • Chloroformic acid, phenylmethyl ester
    • UN 1739
    • benzyloxycarbonylchloride
    • Bzcf
    • Cbz-chloride
    • benylchloroformate
    • benzylchoroformate
    • benzyl chlorformate
    • benzyl choroformate
    • BnOCOCl
    • carbobenzoxychioride
    • carbobenzoxychloride
    • benzyl chioroformate
    • benzyl-chloroformate
    • benzylchloro-formate
    • CBZCl
    • benzylchlorocarbonate
    • carbobenzyloxychloride
    • Benzyl chloro-formate
    • Benzyl chloroform ate
    • benzyl carbonchloridate
    • Benzyl chloroformate (50% in toluene)
    • BnOC(O)Cl
    • benzoxycarbonyl chloride
    • Benzyl chloridocarbonate
    • phenylmethylchlorocarbonate
    • Benzyl chloridocarbonate #
    • benzyloxy carbonyl chloride
    • SCHEMBL960
    • WLN: GVO1R
    • (phenylmethyl)carbonochloridate
    • (phenylmethyl) carbonochloridate
    • Formic acid, chlorobenzyl ester
    • Carbobenzoxy chloride;Z-chloride
    • CHEMBL1581748
    • Formic acid, chloro, benzyl ester
    • AAA50153
    • Chlorocarbonic acid monobenzyl ester
    • NSC83466
    • Tox21_201072
    • BBL011517
    • STL146633
    • AKOS000120065
    • NCGC00090933-01
    • NCGC00090933-02
    • NCGC00258625-01
    • CAS-501-53-1
    • PD118845
    • VS-02967
    • Benzyl chloroformate (30-35% in Toluene)
    • DB-002647
    • B3021
    • NS00003708
    • Benzyl chloroformate [UN1739] [Corrosive]
    • EN300-19843
    • M02865
    • Q419534
    • F0001-1308

  • Applications

    Chemical name: Benzyl chloroformate; CAS 501-53-1. It is primarily used as a reagent to install the benzyloxycarbonyl (Cbz) protecting group on amines, enabling selective protection during multi-step organic synthesis in pharmaceuticals, fine chemicals, and peptide/peptidomimetic workflows, with deprotection typically achieved by hydrogenolysis. It also serves as a convenient precursor for carbamate (urethane) functionalities from amines, supporting the preparation of protected amines and peptidic or peptidomimetic intermediates in medicinal chemistry. Additionally, it can be employed in acylation steps to generate related carbamate derivatives used in drug discovery and industrial chemical manufacturing. Overall, benzyl chloroformate is a valuable tool for amine protection and carbamate installation across pharmaceutical, fine chemical, and synthetic biology applications, with usage governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 254.82
    methanol 242.84
    isopropanol 132.68
    water 0.44
    ethyl acetate 556.35
    n-propanol 167.71
    acetone 1016.52
    n-butanol 125.9
    acetonitrile 392.47
    DMF 2311.7
    toluene 282.26
    isobutanol 106.17
    1,4-dioxane 591.87
    methyl acetate 680.79
    THF 1118.74
    2-butanone 770.23
    n-pentanol 110.02
    sec-butanol 156.75
    n-hexane 5.81
    ethylene glycol 77.45
    NMP 1903.52
    cyclohexane 8.2
    DMSO 1697.66
    n-butyl acetate 252.39
    n-octanol 42.35
    chloroform 553.62
    n-propyl acetate 308.86
    acetic acid 384.91
    dichloromethane 750.89
    cyclohexanone 532.8
    propylene glycol 91.15
    isopropyl acetate 293.3
    DMAc 1827.69
    2-ethoxyethanol 367.42
    isopentanol 123.53
    n-heptane 5.97
    ethyl formate 262.0
    1,2-dichloroethane 730.79
    n-hexanol 92.19
    2-methoxyethanol 616.33
    isobutyl acetate 138.5
    tetrachloromethane 61.38
    n-pentyl acetate 128.63
    transcutol 1941.28
    n-heptanol 43.07
    ethylbenzene 121.54
    MIBK 231.88
    2-propoxyethanol 277.16
    tert-butanol 171.99
    MTBE 288.03
    2-butoxyethanol 157.97
    propionic acid 235.47
    o-xylene 165.5
    formic acid 223.1
    diethyl ether 272.42
    m-xylene 142.22
    p-xylene 129.02
    chlorobenzene 316.74
    dimethyl carbonate 393.62
    n-octane 1.78
    formamide 775.17
    cyclopentanone 1086.26
    2-pentanone 531.33
    anisole 453.33
    cyclopentyl methyl ether 433.82
    gamma-butyrolactone 1212.53
    1-methoxy-2-propanol 427.62
    pyridine 839.05
    3-pentanone 400.72
    furfural 1127.97
    n-dodecane 1.53
    diethylene glycol 256.99
    diisopropyl ether 73.12
    tert-amyl alcohol 208.82
    acetylacetone 814.36
    n-hexadecane 1.87
    acetophenone 454.82
    methyl propionate 547.59
    isopentyl acetate 208.63
    trichloroethylene 1829.52
    n-nonanol 38.76
    cyclohexanol 111.05
    benzyl alcohol 278.44
    2-ethylhexanol 62.23
    isooctanol 38.09
    dipropyl ether 97.43
    1,2-dichlorobenzene 305.24
    ethyl lactate 133.63
    propylene carbonate 540.57
    n-methylformamide 813.81
    2-pentanol 103.82
    n-pentane 6.04
    1-propoxy-2-propanol 184.75
    1-methoxy-2-propyl acetate 366.78
    2-(2-methoxypropoxy) propanol 250.26
    mesitylene 65.69
    ε-caprolactone 507.88
    p-cymene 56.1
    epichlorohydrin 1692.45
    1,1,1-trichloroethane 431.82
    2-aminoethanol 140.56
    morpholine-4-carbaldehyde 1161.9
    sulfolane 1390.49
    2,2,4-trimethylpentane 7.34
    2-methyltetrahydrofuran 725.73
    n-hexyl acetate 179.12
    isooctane 4.51
    2-(2-butoxyethoxy)ethanol 344.39
    sec-butyl acetate 209.46
    tert-butyl acetate 349.6
    decalin 10.61
    glycerin 149.85
    diglyme 847.73
    acrylic acid 306.05
    isopropyl myristate 54.58
    n-butyric acid 243.39
    acetyl acetate 383.67
    di(2-ethylhexyl) phthalate 69.8
    ethyl propionate 277.75
    nitromethane 1442.86
    1,2-diethoxyethane 344.56
    benzonitrile 294.47
    trioctyl phosphate 38.61
    1-bromopropane 196.53
    gamma-valerolactone 1109.21
    n-decanol 27.4
    triethyl phosphate 87.17
    4-methyl-2-pentanol 59.71
    propionitrile 207.51
    vinylene carbonate 424.68
    1,1,2-trichlorotrifluoroethane 877.37
    DMS 339.02
    cumene 66.28
    2-octanol 29.46
    2-hexanone 311.72
    octyl acetate 75.99
    limonene 79.91
    1,2-dimethoxyethane 627.76
    ethyl orthosilicate 75.51
    tributyl phosphate 59.51
    diacetone alcohol 404.47
    N,N-dimethylaniline 282.49
    acrylonitrile 407.48
    aniline 350.42
    1,3-propanediol 175.9
    bromobenzene 323.73
    dibromomethane 367.25
    1,1,2,2-tetrachloroethane 1042.68
    2-methyl-cyclohexyl acetate 141.48
    tetrabutyl urea 89.4
    diisobutyl methanol 39.57
    2-phenylethanol 199.74
    styrene 178.99
    dioctyl adipate 119.88
    dimethyl sulfate 745.99
    ethyl butyrate 188.02
    methyl lactate 266.4
    butyl lactate 107.86
    diethyl carbonate 130.82
    propanediol butyl ether 192.74
    triethyl orthoformate 112.22
    p-tert-butyltoluene 53.78
    methyl 4-tert-butylbenzoate 217.41
    morpholine 765.35
    tert-butylamine 86.09
    n-dodecanol 19.46
    dimethoxymethane 812.36
    ethylene carbonate 289.84
    cyrene 284.55
    2-ethoxyethyl acetate 327.22
    2-ethylhexyl acetate 163.17
    1,2,4-trichlorobenzene 433.19
    4-methylpyridine 859.04
    dibutyl ether 72.49
    2,6-dimethyl-4-heptanol 39.57
    DEF 783.32
    dimethyl isosorbide 470.71
    tetrachloroethylene 614.11
    eugenol 208.84
    triacetin 283.23
    span 80 155.46
    1,4-butanediol 78.11
    1,1-dichloroethane 438.26
    2-methyl-1-pentanol 124.65
    methyl formate 613.6
    2-methyl-1-butanol 137.08
    n-decane 2.61
    butyronitrile 177.38
    3,7-dimethyl-1-octanol 58.41
    1-chlorooctane 26.6
    1-chlorotetradecane 9.33
    n-nonane 2.41
    undecane 1.95
    tert-butylcyclohexane 9.58
    cyclooctane 3.6
    cyclopentanol 164.0
    tetrahydropyran 373.51
    tert-amyl methyl ether 270.39
    2,5,8-trioxanonane 501.28
    1-hexene 44.61
    2-isopropoxyethanol 248.25
    2,2,2-trifluoroethanol 187.32
    methyl butyrate 368.75

    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