Hexamethyleneimine

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  • Identifiers

    CAS number
    111-49-9

    Molecular formula
    C6H13N

    SMILES
    C1CCCNCC1

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Animal 69.63%
    Fishy 66.05%
    Floral 58.09%
    Sweet 56.57%
    Cheesy 41.08%
    Musk 28.72%
    Musty 27.68%
    Ripe 23.85%
    Powdery 23.0%
    Oily 21.56%

     

    Flavor
    Animal 61.97%
    Floral 57.08%
    Sweet 56.17%
    Bitter 55.38%
    Ammoniacal 43.99%
    Amine 38.67%
    Alkaline 31.61%
    Egg 31.01%
    Shrimp 25.8%
    Heavy 25.35%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    8.46 (weak base)

    Molecular weight
    99.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -37 °C

    Boiling point

    • 270 °F at 760 mmHg (USCG, 1999)
    • 138 °C

    Flash point

    • 32.65 ˚C est.
    • 99 °F (USCG, 1999)
    • 99 °F OC

    Solubility expt.

    • Very soluble in ethanol and ethyl ether
    • In water, 3.19X10+4 mg/l @ 25 °C

  • Synonyms

    • Hexamethyleneimine
    • Azepane
    • 111-49-9
    • Hexahydroazepine
    • Perhydroazepine
    • HEXAMETHYLENIMINE
    • Hexahydro-1H-azepine
    • Homopiperidine
    • 1H-Azepine, hexahydro-
    • Azacycloheptane
    • azepan
    • Azepine, hexahydro-
    • 1-Azacycloheptane
    • Cyclohexamethylenimine
    • Hexamethylene imine
    • Cycloheptane, 1-aza-
    • NSC 16236
    • HSDB 562
    • EINECS 203-875-9
    • UNII-CZD076G73R
    • MFCD00006934
    • UN2493
    • BRN 0001084
    • CCRIS 8886
    • CP 18407
    • DTXSID1026879
    • CHEBI:32616
    • AI3-26610
    • NSC-16236
    • CZD076G73R
    • DTXCID906879
    • G 0
    • HEXAMETHYLENEIMINE [HSDB]
    • EC 203-875-9
    • 5-20-04-00003 (Beilstein Handbook Reference)
    • UN 2493
    • CAS-111-49-9
    • G 0 (amine)
    • 1Azacycloheptane
    • Azepane #
    • Hexahydro1Hazepine
    • Azepine, hexahydro
    • Cycloheptane, 1aza
    • 1HAzepine, hexahydro
    • Hexamethyleneimine, 99%
    • WLN: T7MTJ
    • CHEMBL1375444
    • 1-Azacycloheptane; Azacycloheptane
    • 2,3,4,5,6,7-hexahydroazepine
    • CS-B0958
    • NSC16236
    • STR01425
    • Tox21_201482
    • Tox21_303304
    • STL124104
    • AKOS000119078
    • 2,3,4,5,6,7-Hexahydro-1H-azepine
    • NCGC00091040-01
    • NCGC00091040-02
    • NCGC00257117-01
    • NCGC00259033-01
    • BP-30036
    • H0092
    • NS00005885
    • EN300-18063
    • D77224
    • Hexamethyleneimine [UN2493] [Flammable liquid]
    • Q421530
    • Z57127566
    • F2190-0324

  • Applications

    Hexamethyleneimine (CAS 111-49-9) is primarily used as a chemical intermediate in polymer synthesis, serving as a building block for diamine derivatives that feed into polyurethanes and polyamides as well as other high‑performance resins. It can function as a solvent or reaction medium in various industrial processes. It is also used as a precursor in coatings and adhesive formulations, where it enables crosslinking and resin hardening. It is employed in the production of specialty polymers and resins for electronics or advanced materials where cyclic amine chemistry is desired. In addition, it is sometimes evaluated for use in other specialty syntheses and as a reactive intermediate in process chemistry, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1100.24
    methanol 1443.96
    isopropanol 603.5
    water 2.77
    ethyl acetate 1090.97
    n-propanol 965.51
    acetone 888.18
    n-butanol 920.88
    acetonitrile 872.84
    DMF 1172.98
    toluene 443.21
    isobutanol 495.76
    1,4-dioxane 1137.26
    methyl acetate 722.99
    THF 2225.14
    2-butanone 824.96
    n-pentanol 485.12
    sec-butanol 563.82
    n-hexane 169.75
    ethylene glycol 235.32
    NMP 1137.26
    cyclohexane 327.01
    DMSO 1394.67
    n-butyl acetate 832.17
    n-octanol 183.21
    chloroform 3788.09
    n-propyl acetate 453.18
    acetic acid 1270.84
    dichloromethane 2662.44
    cyclohexanone 1164.51
    propylene glycol 287.93
    isopropyl acetate 458.35
    DMAc 660.99
    2-ethoxyethanol 540.0
    isopentanol 466.55
    n-heptane 233.4
    ethyl formate 801.29
    1,2-dichloroethane 1338.97
    n-hexanol 628.81
    2-methoxyethanol 1077.03
    isobutyl acetate 222.87
    tetrachloromethane 767.2
    n-pentyl acetate 372.66
    transcutol 1115.4
    n-heptanol 254.37
    ethylbenzene 136.26
    MIBK 293.6
    2-propoxyethanol 791.73
    tert-butanol 471.62
    MTBE 385.67
    2-butoxyethanol 421.47
    propionic acid 990.57
    o-xylene 195.2
    formic acid 437.77
    diethyl ether 979.82
    m-xylene 199.81
    p-xylene 176.34
    chlorobenzene 815.44
    dimethyl carbonate 185.52
    n-octane 66.6
    formamide 512.87
    cyclopentanone 1631.44
    2-pentanone 795.32
    anisole 284.14
    cyclopentyl methyl ether 816.65
    gamma-butyrolactone 1846.28
    1-methoxy-2-propanol 662.65
    pyridine 1899.06
    3-pentanone 616.47
    furfural 1573.95
    n-dodecane 31.9
    diethylene glycol 492.96
    diisopropyl ether 169.31
    tert-amyl alcohol 389.84
    acetylacetone 615.27
    n-hexadecane 34.34
    acetophenone 266.87
    methyl propionate 699.76
    isopentyl acetate 422.13
    trichloroethylene 2473.56
    n-nonanol 165.41
    cyclohexanol 577.02
    benzyl alcohol 312.55
    2-ethylhexanol 340.2
    isooctanol 165.33
    dipropyl ether 642.46
    1,2-dichlorobenzene 569.05
    ethyl lactate 180.37
    propylene carbonate 906.71
    n-methylformamide 904.61
    2-pentanol 463.33
    n-pentane 218.5
    1-propoxy-2-propanol 604.65
    1-methoxy-2-propyl acetate 441.26
    2-(2-methoxypropoxy) propanol 190.27
    mesitylene 109.64
    ε-caprolactone 1034.66
    p-cymene 135.62
    epichlorohydrin 1481.55
    1,1,1-trichloroethane 1275.65
    2-aminoethanol 512.68
    morpholine-4-carbaldehyde 918.37
    sulfolane 1441.07
    2,2,4-trimethylpentane 53.75
    2-methyltetrahydrofuran 1258.77
    n-hexyl acetate 327.17
    isooctane 36.48
    2-(2-butoxyethoxy)ethanol 349.43
    sec-butyl acetate 224.97
    tert-butyl acetate 314.27
    decalin 65.86
    glycerin 385.14
    diglyme 729.38
    acrylic acid 834.29
    isopropyl myristate 111.34
    n-butyric acid 1539.3
    acetyl acetate 580.29
    di(2-ethylhexyl) phthalate 108.08
    ethyl propionate 391.72
    nitromethane 1445.0
    1,2-diethoxyethane 629.0
    benzonitrile 599.02
    trioctyl phosphate 88.09
    1-bromopropane 1094.03
    gamma-valerolactone 1406.38
    n-decanol 118.24
    triethyl phosphate 157.02
    4-methyl-2-pentanol 167.97
    propionitrile 1011.7
    vinylene carbonate 822.41
    1,1,2-trichlorotrifluoroethane 1095.58
    DMS 192.36
    cumene 84.04
    2-octanol 143.7
    2-hexanone 394.86
    octyl acetate 156.38
    limonene 237.61
    1,2-dimethoxyethane 742.28
    ethyl orthosilicate 163.41
    tributyl phosphate 121.67
    diacetone alcohol 333.46
    N,N-dimethylaniline 163.92
    acrylonitrile 1199.39
    aniline 697.96
    1,3-propanediol 648.87
    bromobenzene 814.3
    dibromomethane 1986.1
    1,1,2,2-tetrachloroethane 1842.05
    2-methyl-cyclohexyl acetate 213.78
    tetrabutyl urea 148.33
    diisobutyl methanol 162.56
    2-phenylethanol 351.18
    styrene 245.84
    dioctyl adipate 154.45
    dimethyl sulfate 279.6
    ethyl butyrate 542.56
    methyl lactate 284.48
    butyl lactate 254.43
    diethyl carbonate 275.98
    propanediol butyl ether 256.32
    triethyl orthoformate 333.14
    p-tert-butyltoluene 120.95
    methyl 4-tert-butylbenzoate 192.92
    morpholine 1445.75
    tert-butylamine 357.89
    n-dodecanol 90.76
    dimethoxymethane 646.75
    ethylene carbonate 704.99
    cyrene 198.94
    2-ethoxyethyl acetate 407.71
    2-ethylhexyl acetate 367.27
    1,2,4-trichlorobenzene 583.02
    4-methylpyridine 1121.63
    dibutyl ether 374.84
    2,6-dimethyl-4-heptanol 162.56
    DEF 902.1
    dimethyl isosorbide 329.79
    tetrachloroethylene 1546.58
    eugenol 195.33
    triacetin 262.83
    span 80 261.37
    1,4-butanediol 205.04
    1,1-dichloroethane 1402.26
    2-methyl-1-pentanol 283.78
    methyl formate 557.67
    2-methyl-1-butanol 466.46
    n-decane 61.78
    butyronitrile 1023.51
    3,7-dimethyl-1-octanol 167.15
    1-chlorooctane 170.58
    1-chlorotetradecane 60.81
    n-nonane 69.79
    undecane 41.52
    tert-butylcyclohexane 50.01
    cyclooctane 100.57
    cyclopentanol 711.69
    tetrahydropyran 1453.69
    tert-amyl methyl ether 284.73
    2,5,8-trioxanonane 405.31
    1-hexene 442.34
    2-isopropoxyethanol 291.58
    2,2,2-trifluoroethanol 364.27
    methyl butyrate 543.53

    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