4-Chloro-2-methylaniline

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  • Identifiers

    CAS number
    95-69-2

    Molecular formula
    C7H8ClN

    SMILES
    CC1=C(C=CC(=C1)Cl)N

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Animal 42.35%
    Phenolic 42.32%
    Sweet 37.76%
    Floral 33.22%
    Burnt 30.05%
    Smoky 29.49%
    Musty 28.65%
    Leathery 28.61%
    Woody 26.46%
    Meaty 25.4%

     

    Flavor
    Phenolic 32.22%
    Meaty 32.13%
    Mild 28.68%
    Medicinal 24.64%
    Roasted 23.98%
    Sulfurous 22.8%
    Penetrating 21.42%
    Very strong 21.42%
    Flat 21.25%
    Indole 21.11%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    4.47 (weak acid)

    Molecular weight
    141.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 72 °F (NTP, 1992)
    • 30 °C
    • 29-30 °C
    • 72 °F

    Boiling point

    • 466 °F at 760 mmHg (NTP, 1992)
    • 241 °C @ 760 MM HG
    • 241 °C
    • 466 °F

    Flash point

    • 114.96 ˚C est.
    • 320 °F (NTP, 1992)
    • 99 °C c.c.
    • 320 °F

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • SOL IN HOT ALCOHOL
    • SPARINGLY SOL IN WATER, SOL IN ETHANOL & DILUTE ACIDS
    • Solubility in water, g/100ml at 25 °C: 0.095 (very poor)

  • Synonyms

    • 4-Chloro-2-methylaniline
    • 95-69-2
    • 4-CHLORO-O-TOLUIDINE
    • 2-Amino-5-chlorotoluene
    • p-Chloro-o-toluidine
    • Fast Red TR Base
    • Benzenamine, 4-chloro-2-methyl-
    • Kambamine Red TR
    • Red TR base
    • 4-Chloro-2-toluidine
    • Kako Red TR Base
    • Daito Red Base TR
    • o-Toluidine, 4-chloro-
    • Mitsui Red TR Base
    • 2-Methyl-4-chloroaniline
    • Deval Red K
    • Deval Red TR
    • Fast Red TR
    • Red Base NTR
    • Fast Red Base TR
    • Red Base Ciba IX
    • Red Base Irga IX
    • 5-Chloro-2-aminotoluene
    • Sanyo Fast Red TR Base
    • Fast Red Tr11
    • 4-Chloro-6-methylaniline
    • Fast Red TRO Base
    • Diazo Fast Red TRA
    • Fast Red 5CT Base
    • Tulabase Fast Red TR
    • 3-Chloro-6-aminotoluene
    • Azoene Fast Red TR Base
    • Amarthol Fast Red TR Base
    • Brentamine Fast Red TR Base
    • 4-Chloro-2-methylbenzeneamine
    • Azoic Diazo Component 11, base
    • 4-Chloro-ortho-toluidine
    • NSC 4979
    • 4-Chloro-2-methylbenzenamine
    • DTXSID1041508
    • CHEBI:82276
    • NSC-4979
    • 87999-30-2
    • 95NB978426
    • Benzenamine, 4-chloro-2-methyl-, labeled with carbon-14, hydrochloride
    • 4-Chloro-2-methylaniline 100 microg/mL in Methanol
    • Caswell No. 216H
    • 4-chloro-2-methylphenylamine
    • 4-CHLORO-2-METHYL-PHENYLAMINE
    • CCRIS 7518
    • HSDB 2061
    • 4-chloro-o-methylaniline
    • EINECS 202-441-6
    • Asymmetric meta-chloro-ortho-toluidine
    • 4-chloro-2-methyl aniline
    • BRN 0878505
    • UNII-95NB978426
    • MFCD00007842
    • Fast Red TR-T Base
    • Devol Red K (Salt/Mix)
    • WLN: ZR DG B1
    • Kromon Green B (Salt/Mix)
    • SCHEMBL92153
    • 4-12-00-01796 (Beilstein Handbook Reference)
    • NSC 7629 (Salt/Mix)
    • aniline, 4-chloro-2-methyl-
    • CHEMBL3181910
    • DTXCID9021508
    • NCI-C02368 (Salt/Mix)
    • Neutrosel Red TRVA (Salt/Mix)
    • NSC4979
    • 4-Chloro-2-methylaniline, 98%
    • Azogene Fast Red TR (Salt/Mix)
    • STR01685
    • Tox21_300857
    • STL163571
    • AKOS000118867
    • CS-W007906
    • FC64323
    • CAS-95-69-2
    • 4-CHLORO-ORTHO-TOLUIDINE [IARC]
    • NCGC00248193-01
    • NCGC00248193-02
    • NCGC00254760-01
    • BP-11292
    • DB-024295
    • A0704
    • NS00004103
    • 4-Chloro-2-methylaniline, analytical standard
    • EN300-19546
    • C19169
    • D78538
    • 4-Chloro-2-methylaniline, purum, >=98.0% (GC)
    • Q10859489
    • F1995-0194
    • Z104474180
    • InChI=1/C7H8ClN/c1-5-4-6(8)2-3-7(5)9/h2-4H,9H2,1H
    • 4-Chloro-o-toluidine; 2-Amino-5-chlorotoluene; 2-Methyl-4-chloroaniline; 4-Chloro-2-methylbenzenamine; 4-Chloro-6-methylaniline; 5-Chloro-2-aminotoluene

  • Applications

    4-Chloro-2-methylaniline (CAS 95-69-2) is primarily used as an aromatic amine building block in organic synthesis. In industry, it serves as an intermediate for the production of dyes and pigments, including azo dye chemistries, and as a precursor to other specialty amines for coatings and inks. It is also employed as a starting material in pharmaceutical and agrochemical synthesis, enabling selective substitutions on the aniline ring to construct more complex active ingredients. In polymer and plastics applications, it can function as a building block for specialty chemicals and crosslinking routes, contributing to material design. Use and handling are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 119.38
    methanol 128.34
    isopropanol 79.24
    water 3.46
    ethyl acetate 168.39
    n-propanol 102.43
    acetone 193.38
    n-butanol 92.59
    acetonitrile 138.59
    DMF 248.32
    toluene 42.28
    isobutanol 54.83
    1,4-dioxane 256.76
    methyl acetate 178.22
    THF 359.68
    2-butanone 200.5
    n-pentanol 69.85
    sec-butanol 68.73
    n-hexane 2.39
    ethylene glycol 22.47
    NMP 113.62
    cyclohexane 2.09
    DMSO 133.55
    n-butyl acetate 119.74
    n-octanol 40.63
    chloroform 174.88
    n-propyl acetate 84.88
    acetic acid 117.04
    dichloromethane 120.2
    cyclohexanone 126.98
    propylene glycol 29.71
    isopropyl acetate 79.04
    DMAc 241.3
    2-ethoxyethanol 137.05
    isopentanol 68.75
    n-heptane 6.78
    ethyl formate 116.58
    1,2-dichloroethane 79.28
    n-hexanol 95.1
    2-methoxyethanol 178.02
    isobutyl acetate 57.8
    tetrachloromethane 35.57
    n-pentyl acetate 63.65
    transcutol 270.84
    n-heptanol 55.72
    ethylbenzene 20.31
    MIBK 64.62
    2-propoxyethanol 171.17
    tert-butanol 98.19
    MTBE 101.48
    2-butoxyethanol 113.83
    propionic acid 81.22
    o-xylene 26.38
    formic acid 67.58
    diethyl ether 100.85
    m-xylene 30.81
    p-xylene 29.66
    chlorobenzene 55.81
    dimethyl carbonate 74.23
    n-octane 3.59
    formamide 134.41
    cyclopentanone 203.37
    2-pentanone 126.21
    anisole 81.49
    cyclopentyl methyl ether 97.69
    gamma-butyrolactone 206.38
    1-methoxy-2-propanol 119.17
    pyridine 145.34
    3-pentanone 89.54
    furfural 184.65
    n-dodecane 2.98
    diethylene glycol 109.84
    diisopropyl ether 23.23
    tert-amyl alcohol 79.37
    acetylacetone 131.71
    n-hexadecane 3.28
    acetophenone 66.77
    methyl propionate 123.02
    isopentyl acetate 88.33
    trichloroethylene 193.03
    n-nonanol 36.53
    cyclohexanol 38.38
    benzyl alcohol 59.17
    2-ethylhexanol 53.03
    isooctanol 43.32
    dipropyl ether 66.02
    1,2-dichlorobenzene 50.37
    ethyl lactate 40.1
    propylene carbonate 104.03
    n-methylformamide 151.72
    2-pentanol 50.92
    n-pentane 2.55
    1-propoxy-2-propanol 114.13
    1-methoxy-2-propyl acetate 108.66
    2-(2-methoxypropoxy) propanol 77.88
    mesitylene 18.01
    ε-caprolactone 116.39
    p-cymene 21.99
    epichlorohydrin 216.63
    1,1,1-trichloroethane 108.98
    2-aminoethanol 55.33
    morpholine-4-carbaldehyde 180.79
    sulfolane 135.31
    2,2,4-trimethylpentane 3.88
    2-methyltetrahydrofuran 175.06
    n-hexyl acetate 70.42
    isooctane 3.63
    2-(2-butoxyethoxy)ethanol 109.26
    sec-butyl acetate 55.0
    tert-butyl acetate 80.39
    decalin 3.48
    glycerin 51.66
    diglyme 204.54
    acrylic acid 68.54
    isopropyl myristate 27.97
    n-butyric acid 126.0
    acetyl acetate 92.06
    di(2-ethylhexyl) phthalate 31.36
    ethyl propionate 65.23
    nitromethane 254.57
    1,2-diethoxyethane 120.32
    benzonitrile 61.57
    trioctyl phosphate 23.51
    1-bromopropane 38.91
    gamma-valerolactone 243.49
    n-decanol 27.79
    triethyl phosphate 35.9
    4-methyl-2-pentanol 35.99
    propionitrile 100.45
    vinylene carbonate 111.32
    1,1,2-trichlorotrifluoroethane 133.23
    DMS 55.14
    cumene 16.99
    2-octanol 34.51
    2-hexanone 91.06
    octyl acetate 37.89
    limonene 29.23
    1,2-dimethoxyethane 217.08
    ethyl orthosilicate 38.79
    tributyl phosphate 28.43
    diacetone alcohol 90.35
    N,N-dimethylaniline 50.27
    acrylonitrile 108.55
    aniline 66.78
    1,3-propanediol 86.8
    bromobenzene 48.61
    dibromomethane 67.43
    1,1,2,2-tetrachloroethane 137.87
    2-methyl-cyclohexyl acetate 54.26
    tetrabutyl urea 35.76
    diisobutyl methanol 31.73
    2-phenylethanol 74.76
    styrene 24.54
    dioctyl adipate 37.12
    dimethyl sulfate 83.95
    ethyl butyrate 78.11
    methyl lactate 55.12
    butyl lactate 50.75
    diethyl carbonate 51.74
    propanediol butyl ether 70.0
    triethyl orthoformate 58.01
    p-tert-butyltoluene 23.85
    methyl 4-tert-butylbenzoate 64.12
    morpholine 228.33
    tert-butylamine 48.76
    n-dodecanol 21.2
    dimethoxymethane 174.44
    ethylene carbonate 90.38
    cyrene 76.79
    2-ethoxyethyl acetate 97.33
    2-ethylhexyl acetate 72.01
    1,2,4-trichlorobenzene 60.95
    4-methylpyridine 131.96
    dibutyl ether 43.54
    2,6-dimethyl-4-heptanol 31.73
    DEF 111.7
    dimethyl isosorbide 128.82
    tetrachloroethylene 99.0
    eugenol 71.33
    triacetin 61.9
    span 80 63.23
    1,4-butanediol 37.64
    1,1-dichloroethane 99.9
    2-methyl-1-pentanol 58.3
    methyl formate 119.21
    2-methyl-1-butanol 62.4
    n-decane 4.93
    butyronitrile 102.91
    3,7-dimethyl-1-octanol 37.52
    1-chlorooctane 21.32
    1-chlorotetradecane 8.75
    n-nonane 4.48
    undecane 3.7
    tert-butylcyclohexane 5.35
    cyclooctane 1.33
    cyclopentanol 53.32
    tetrahydropyran 153.33
    tert-amyl methyl ether 68.8
    2,5,8-trioxanonane 134.92
    1-hexene 15.76
    2-isopropoxyethanol 90.91
    2,2,2-trifluoroethanol 66.28
    methyl butyrate 84.73

    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