Diphenylamine

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  • Identifiers

    CAS number
    122-39-4

    Molecular formula
    C12H11N

    SMILES
    C1=CC=C(C=C1)NC2=CC=CC=C2

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Floral 79.98%
    Sweet 68.5%
    Rose 46.84%
    Honey 41.37%
    Animal 38.58%
    Fruity 30.35%
    Balsamic 27.4%
    Grape 27.2%
    Orange 25.81%
    Waxy 25.78%

    Scent© AI

    Odor threshold>

    • Odor Threshold Low: 0.02 [mmHg]. Odor threshold from AIHA
    • Odor perception threshold is 0.05 mg/L.

  • Properties

    XLogP3-AA
    3.5

    Molecular weight
    169.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 129 to 131 °F (NTP, 1992)
    • 53-54 °C
    • 52 - 54 °C
    • 53 °C
    • 127 °F

    Boiling point

    • 576 °F at 760 mmHg (NTP, 1992)
    • 302 °C
    • 302.00 °C. @ 760.00 mm Hg
    • 576 °F

    Flash point est.
    140.99 ˚C

    Flash point expt.

    • 307 °F (NTP, 1992)
    • 307 °F
    • 153 °C OC
    • 153 °C c.c.

    Solubility expt.

    • less than 1 mg/mL at 61 °F (NTP, 1992)
    • 1 g dissolves in 2.2 ml of alcohol, 4 ml propyl alcohol; Freely sol in benzene, ether, glacial acetic acid, carbon disulfide.
    • Very sol in ethanol, acetone, benzene, carbon tetrachloride, pyridine, ethyl acetate; sol in ether, acetic acid; slightly sol in chloroform
    • Soluble in oxygenated and aromatic solvents
    • In water, 53 mg/liter @ 20 °C
    • 0.053 mg/mL at 20 °C
    • Solubility in water: very poor
    • 0.03%

  • Synonyms

    • Diphenylamine
    • N-Phenylaniline
    • 122-39-4
    • N,N-DIPHENYLAMINE
    • N-Phenylbenzenamine
    • Anilinobenzene
    • N-Phenylbenzeneamine
    • Phenylaniline
    • Scaldip
    • Big Dipper
    • Benzenamine, N-phenyl-
    • Styrenated diphenylamine
    • Aniline, N-phenyl-
    • No-Scald
    • Benzene, anilino-
    • Difenylamin
    • Deccoscald 282
    • Naugalube 428L
    • N-Fenylanilin
    • Shield DPA
    • No-Scald DPA 283
    • Benzene, (phenylamino)-
    • (phenylamino)benzene
    • Caswell No. 398
    • DIPHENYL-AMINE
    • No scald
    • C.I. 10355
    • C6H5-NH-C6H5
    • CCRIS 4699
    • CHEBI:4640
    • N-Phenylbenzenamine, styrenated
    • NSC 215210
    • HSDB 1108
    • UNII-9N3CBB0BIQ
    • 9N3CBB0BIQ
    • DFA
    • EINECS 204-539-4
    • MFCD00003014
    • EPA Pesticide Chemical Code 038501
    • CI 10355
    • DTXSID4021975
    • AI3-00781
    • NSC-215210
    • DTXCID001975
    • EC 204-539-4
    • Difenylamin [Czech]
    • DIPHENYL AMINE
    • N-Fenylanilin [Czech]
    • 25656-57-9
    • CAS-122-39-4
    • Diphenylamine indicator
    • DIPHENYLAMINE, ACS
    • phenyl aniline
    • Anilino-Benzene
    • n-phenyl-aniline
    • N-phenylbenzamine
    • N-(phenyl)aniline
    • n,n-diphenyl amine
    • EINECS 270-485-3
    • N,N-di-phenylamine
    • n-phenyl-benzenamine
    • Diphenylamine, p.a.
    • (phenylamino)-Benzene
    • No scald dpa 283
    • Ph2NH
    • Diphenylamine, >=98%
    • WLN: RMR
    • Diphenylamine, ACS grade
    • N-Phenylbenzenamine, 9CI
    • SCHEMBL229
    • DIPHENYLAMINE [MI]
    • Epitope ID:115002
    • Oprea1_815288
    • MLS002152913
    • BIDD:ER0338
    • CHEMBL38688
    • QSPL 033
    • SCHEMBL3685153
    • SCHEMBL6255037
    • SCHEMBL7527678
    • SCHEMBL10932134
    • 2-Biphenylyl-N-pyridyl-Acetamide
    • N,N-DIPHENYLAMINE [HSDB]
    • HMS1788N11
    • HMS3034E05
    • Tox21_201611
    • Tox21_301026
    • NSC215210
    • STK301666
    • Diphenylamine, ACS reagent, >=99%
    • Diphenylamine, ReagentPlus(R), 99%
    • AKOS000119099
    • NC-0220
    • USEPA/OPP Pesticide Code: 038501
    • NCGC00090889-01
    • NCGC00090889-02
    • NCGC00090889-03
    • NCGC00090889-04
    • NCGC00090889-05
    • NCGC00254928-01
    • NCGC00259160-01
    • AC-16417
    • SMR000777939
    • Diphenylamine 10 microg/mL in Cyclohexane
    • D0872
    • D1229
    • Diphenylamine 100 microg/mL in Acetonitrile
    • NS00010366
    • Diphenylamine, Vetec(TM) reagent grade, 98%
    • EN300-18732
    • Diphenylamine 1000 microg/mL in Dichloromethane
    • Diphenylamine, PESTANAL(R), analytical standard
    • A804887
    • AE-641/01947044
    • Q412265
    • Z90121252
    • F2190-0411
    • Diphenylamine, puriss. p.a., redox indicator, ACS reagent, reag. Ph. Eur., >=98% (GC)
    • InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13
    • 204-539-4

  • Applications

    Diphenylamine (DPA, CAS 122-39-4) is an aromatic amine widely used as an antioxidant and stabilizer: it protects lubricating oils, greases, and fuels from oxidation/deposit formation; extends the service life of rubber and plastics; stabilizes gasoline and jet fuel; inhibits unwanted polymerization in monomers (e.g., styrene) and helps protect polymers from heat/UV via precursor alkylated diphenylamine antioxidants; serves as a stabilizer in propellants and nitrocellulose materials; functions as an intermediate for dyes, agrochemicals, and pharmaceuticals; is applied postharvest to reduce superficial scald in apples/pears; acts as a corrosion inhibitor in metalworking fluids; is a component in photographic processes; serves as an analytical reagent (redox indicator, nitrate/nitrite detection); and is used in inks, coatings, and adhesives; its uses are subject to safety, residue, and environmental regulations, requiring appropriate exposure controls and waste management.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 38.87
    methanol 28.88
    isopropanol 24.11
    water 0.05
    ethyl acetate 182.88
    n-propanol 37.67
    acetone 321.57
    n-butanol 35.43
    acetonitrile 101.65
    DMF 443.1
    toluene 73.84
    isobutanol 24.63
    1,4-dioxane 335.42
    methyl acetate 147.65
    THF 883.47
    2-butanone 219.65
    n-pentanol 33.44
    sec-butanol 27.24
    n-hexane 33.3
    ethylene glycol 9.0
    NMP 360.02
    cyclohexane 36.63
    DMSO 412.26
    n-butyl acetate 139.73
    n-octanol 30.14
    chloroform 497.59
    n-propyl acetate 115.93
    acetic acid 90.53
    dichloromethane 456.87
    cyclohexanone 305.03
    propylene glycol 18.3
    isopropyl acetate 97.82
    DMAc 412.82
    2-ethoxyethanol 56.16
    isopentanol 30.44
    n-heptane 35.48
    ethyl formate 106.05
    1,2-dichloroethane 328.19
    n-hexanol 50.05
    2-methoxyethanol 88.04
    isobutyl acetate 82.27
    tetrachloromethane 36.75
    n-pentyl acetate 62.87
    transcutol 292.57
    n-heptanol 27.57
    ethylbenzene 52.8
    MIBK 90.28
    2-propoxyethanol 83.44
    tert-butanol 39.48
    MTBE 70.72
    2-butoxyethanol 51.29
    propionic acid 69.4
    o-xylene 42.29
    formic acid 13.53
    diethyl ether 127.22
    m-xylene 43.34
    p-xylene 63.15
    chlorobenzene 132.48
    dimethyl carbonate 121.06
    n-octane 12.84
    formamide 34.46
    cyclopentanone 605.01
    2-pentanone 176.65
    anisole 124.17
    cyclopentyl methyl ether 209.88
    gamma-butyrolactone 590.01
    1-methoxy-2-propanol 80.95
    pyridine 314.02
    3-pentanone 167.74
    furfural 325.5
    n-dodecane 9.86
    diethylene glycol 46.6
    diisopropyl ether 40.51
    tert-amyl alcohol 35.69
    acetylacetone 237.26
    n-hexadecane 11.21
    acetophenone 116.53
    methyl propionate 169.87
    isopentyl acetate 103.58
    trichloroethylene 588.44
    n-nonanol 31.02
    cyclohexanol 43.54
    benzyl alcohol 59.27
    2-ethylhexanol 48.16
    isooctanol 25.08
    dipropyl ether 165.21
    1,2-dichlorobenzene 115.46
    ethyl lactate 53.25
    propylene carbonate 276.34
    n-methylformamide 95.7
    2-pentanol 26.33
    n-pentane 13.51
    1-propoxy-2-propanol 84.75
    1-methoxy-2-propyl acetate 121.51
    2-(2-methoxypropoxy) propanol 75.03
    mesitylene 31.94
    ε-caprolactone 215.04
    p-cymene 36.95
    epichlorohydrin 473.78
    1,1,1-trichloroethane 215.94
    2-aminoethanol 18.8
    morpholine-4-carbaldehyde 277.05
    sulfolane 595.95
    2,2,4-trimethylpentane 9.05
    2-methyltetrahydrofuran 305.44
    n-hexyl acetate 86.41
    isooctane 7.49
    2-(2-butoxyethoxy)ethanol 95.63
    sec-butyl acetate 72.74
    tert-butyl acetate 98.17
    decalin 23.66
    glycerin 29.33
    diglyme 240.18
    acrylic acid 74.29
    isopropyl myristate 50.02
    n-butyric acid 105.57
    acetyl acetate 136.91
    di(2-ethylhexyl) phthalate 40.33
    ethyl propionate 122.05
    nitromethane 252.54
    1,2-diethoxyethane 146.48
    benzonitrile 89.64
    trioctyl phosphate 28.46
    1-bromopropane 145.59
    gamma-valerolactone 396.77
    n-decanol 25.09
    triethyl phosphate 62.59
    4-methyl-2-pentanol 22.18
    propionitrile 84.23
    vinylene carbonate 207.98
    1,1,2-trichlorotrifluoroethane 218.92
    DMS 102.77
    cumene 37.44
    2-octanol 19.82
    2-hexanone 126.1
    octyl acetate 56.98
    limonene 58.23
    1,2-dimethoxyethane 224.0
    ethyl orthosilicate 58.07
    tributyl phosphate 39.29
    diacetone alcohol 88.22
    N,N-dimethylaniline 85.46
    acrylonitrile 120.13
    aniline 76.73
    1,3-propanediol 27.03
    bromobenzene 149.56
    dibromomethane 293.15
    1,1,2,2-tetrachloroethane 465.17
    2-methyl-cyclohexyl acetate 85.61
    tetrabutyl urea 57.0
    diisobutyl methanol 37.85
    2-phenylethanol 56.64
    styrene 75.79
    dioctyl adipate 75.5
    dimethyl sulfate 184.68
    ethyl butyrate 131.48
    methyl lactate 71.12
    butyl lactate 47.85
    diethyl carbonate 91.87
    propanediol butyl ether 42.21
    triethyl orthoformate 93.28
    p-tert-butyltoluene 37.06
    methyl 4-tert-butylbenzoate 86.79
    morpholine 274.61
    tert-butylamine 28.24
    n-dodecanol 22.11
    dimethoxymethane 253.9
    ethylene carbonate 175.86
    cyrene 93.4
    2-ethoxyethyl acetate 88.12
    2-ethylhexyl acetate 91.86
    1,2,4-trichlorobenzene 136.55
    4-methylpyridine 196.49
    dibutyl ether 103.62
    2,6-dimethyl-4-heptanol 37.85
    DEF 197.76
    dimethyl isosorbide 166.04
    tetrachloroethylene 229.69
    eugenol 69.35
    triacetin 98.04
    span 80 72.06
    1,4-butanediol 13.01
    1,1-dichloroethane 226.31
    2-methyl-1-pentanol 32.7
    methyl formate 104.31
    2-methyl-1-butanol 28.63
    n-decane 15.48
    butyronitrile 83.82
    3,7-dimethyl-1-octanol 34.23
    1-chlorooctane 45.72
    1-chlorotetradecane 22.15
    n-nonane 15.06
    undecane 11.76
    tert-butylcyclohexane 20.06
    cyclooctane 15.33
    cyclopentanol 73.97
    tetrahydropyran 295.24
    tert-amyl methyl ether 64.05
    2,5,8-trioxanonane 158.91
    1-hexene 81.85
    2-isopropoxyethanol 45.15
    2,2,2-trifluoroethanol 34.42
    methyl butyrate 161.0

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0 %
Category 2
Products applied to the axillae
 0 % Category 7B
Leave-on products applied to the hair with some hand contact
 0 %
Category 3
Products applied to the face/body using fingertips
 0 % Category 8
Products with significant anogenital exposure
 0 %
Category 4
Products related to fine fragrance
 0 % Category 9
Products with body and hand exposure, primarily rinse off
 0 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0 % Category 10A
Household care products with mostly hand contact
 0 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0 %
Category 5D
Baby Creams, baby Oils and baby talc
 0 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0 %
Category 6
Products with oral and lip exposure
 0 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 0 %

Prohibition
Diphenylamine should not be used as a fragrance ingredient.

Botanical

Name CAS Botanical Proportion
Artemisia monosperma Artemisia monosperma Del., fam. Asteraceae (Compositae) 2.0%
Daphne tangutica flower concrete (China) Daphne tangutica Maxim., fam. Thymelaeaceae 1.48%
Fenugreek 1b steamdistillate 84625-40-1 Trigonella foenum-graecum L., fam. Leguminosae 2.5%