Dapsone

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  • Identifiers

    CAS number
    80-08-0

    Molecular formula
    C12H12N2O2S

    SMILES
    C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 50.92%
    Meaty 31.23%
    Burnt 29.09%
    Cooked 28.58%
    Roasted 26.94%
    Sulfurous 26.6%
    Bitter 26.15%
    Grape 25.29%
    Savory 23.38%
    Cheesy 18.48%

     

    Flavor
    Bitter 64.62%
    Odorless 24.83%
    Nitrile 22.21%
    Mild 21.73%
    Bread crust 20.31%
    Very strong 20.29%
    Taco 20.21%
    Indole 19.93%
    Urine 19.71%
    Moth ball 19.62%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    6.02 (neutral)

    Molecular weight
    248.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    571°C

    Melting point expt.

    • 347 to 349 °F (NTP, 1992)
    • 175.5 °C
    • 175-176 °C (also a higher melting form, MP 180.5 °C)
    • There are extraordinarily complicated polymorphism conditions in the drugs dapsone and ethambutol chloride. In both cases, four modifications were detected, and in the case of dapsone there exists a hydrate in addition. The dapsone anhydrate is present as enantiotropic Mod. III, which transforms into Mod. II at 80 °C. This form is mostly stable up to its melting point. Mod. I, which crystallizes from the melt, is likewise enantiotropic with Mod. II. In addition, there is enantiotropy between Mod. I and Mod. III. The transformation of Mod. III /between/ Mod. II takes place continuously and independently from nuclei, so that the melting point of Mod. III cannot be determined. In Mod. IV, no enantiotropy with another crystal form could be detected. ...

    Flash point

    • 271.5 ˚C est.
    • greater than 320 °F (NTP, 1992)
    • Flash point > 320 °F

    Solubility expt.

    • >37.2 [ug/mL] (The mean of the results at pH 7.4)
    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • 380 mg/L (at 37 °C)
    • In water, 380 mg/L at 37 °C
    • Soluble in alcohol, methanol, acetone, dilute hydrochloric acid. Practically insoluble in water.
    • Insoluble in fixed and vegetable oils.
    • Slightly soluble in deuterated dimethyl sulfoxide.
    • 2.84e-01 g/L

  • Synonyms

    • dapsone
    • 80-08-0
    • 4,4'-Sulfonyldianiline
    • 4,4'-Diaminodiphenyl sulfone
    • Diaphenylsulfone
    • 4,4'-Diaminodiphenylsulfone
    • Dapson
    • 4-Aminophenyl sulfone
    • Novophone
    • DADPS
    • Diaphenylsulfon
    • Dapsonum
    • Diphenasone
    • Aczone
    • Sulfona
    • Bis(4-aminophenyl) sulfone
    • p-Aminophenyl sulfone
    • Avlosulfon
    • Avlosulfone
    • Croysulfone
    • Sulfadione
    • Sulphadione
    • Disulone
    • Dumitone
    • Eporal
    • Udolac
    • Sulfona-MAE
    • Bis(p-aminophenyl) sulfone
    • Dapsona
    • Diphone
    • Diaphenylsulphon
    • p,p-Sulphonylbisbenzamine
    • 4,4'-Dapsone
    • Diaphenylsulphone
    • Metabolite C
    • Sulfonyldianiline
    • p,p-Sulphonylbisbenzenamine
    • Sumicure S
    • Sulphonyldianiline
    • 4,4'-Sulfonylbisaniline
    • Avlosulphone
    • Croysulphone
    • Dubronax
    • p,p'-Diaminodiphenyl sulfone
    • Diaminodiphenyl sulfone
    • Tarimyl
    • 4-(4-aminophenyl)sulfonylaniline
    • Sulfone ucb
    • Diaminodiphenylsulfone
    • NSC-6091
    • Bis(4-aminophenyl)sulfone
    • 4,4'-Sulfonylbisbenzamine
    • 4,4'-Sulfonylbisbenzenamine
    • Benzenamine, 4,4'-sulfonylbis-
    • Di(p-aminophenyl) sulfone
    • p,p-Sulphonyldianiline
    • Di(4-aminophenyl) sulfone
    • p,p'-sulfonyldianiline
    • p,p-Sulfonylbisbenzamine
    • Diaminodifenilsulfona
    • Servidapson
    • DDS, pharmaceutical
    • Di(p-aminophenyl)sulphone
    • p,p-Sulfonylbisbenzenamine
    • Sulphon-mere
    • 1,1'-Sulfonylbis(4-aminobenzene)
    • Araldite HT 976
    • Bis(p-aminophenyl)sulphone
    • Di(4-aminophenyl)sulphone
    • Bis(4-aminophenyl)sulphone
    • p,p-Diaminodiphenyl sulphone
    • N,N'-Diphenyl sulfondiamide
    • 4,4'-Sulphonyldianiline
    • 4,4'-Diaminodiphenyl sulphone
    • DDS
    • 4,4'-Sulphonylbisbenzamine
    • 4,4'-Sulphonylbisbenzenamine
    • WR 448
    • 4,4-Diaminodifenylsulfon
    • Diamino-4,4'-diphenyl sulfone
    • Diamino-4,4'-diphenyl sulphone
    • NSC 6091D
    • NCI-C01718
    • 1,1'-Sulfonylbis[4-aminobenzene]
    • 1,1'-Sulphonylbis(4-aminobenzene)
    • 4,4'-Sulfonylbisbenzeneamine
    • Aniline, 4,4'-sulfonyldi-
    • HT 976
    • 1358F
    • 4,4'-Sulfonyldianilin
    • DTXSID4020371
    • F 1358
    • 4,4'-Sulfonyldianiline (Dapsone)
    • 4-[(4-aminophenyl)sulfonyl]aniline
    • 4-[(4-aminobenzene)sulfonyl]aniline
    • MFCD00007887
    • CHEBI:4325
    • NSC-6091D
    • J04BA02
    • NSC6091
    • 4-(4-aminobenzenesulfonyl)aniline
    • Diaphenylsulfone (JAN)
    • CHEMBL1043
    • 4-(4-amino-benzenesulfonyl)-phenylamine
    • DTXCID00371
    • MLS000069409
    • 8W5C518302
    • 4-(4-aminophenylsulfonyl)aniline
    • Sulfanona-mae
    • Sulfon-mere
    • 4,4'-DDS
    • 4-(4-aminophenylsulfonyl)benzenamine
    • 4,4'-Diaminodiphenyl-13C12-sulfone
    • Di(4-aminophenyl)sulfone
    • HT 9664
    • NCGC00016322-08
    • SMR000059064
    • Hardener HT 976
    • DAPSONE (IARC)
    • DAPSONE [IARC]
    • DDS (pharmaceutical)
    • DAPSONE (MART.)
    • DAPSONE [MART.]
    • DAPSONE (USP-RS)
    • DAPSONE [USP-RS]
    • 4,4'-DIAMINO-15N2-DIPHENYL SULFONE
    • Dapsonum [INN-Latin]
    • Dapsona [INN-Spanish]

  • Applications

    Dapsone (CAS 80-08-0) is a sulfone used primarily as an active pharmaceutical ingredient (API) in sulfonamide medicines and also serves as a precursor or building block for the synthesis of related sulfonamide compounds; it is used in cosmetics/personal care in dermatology-type formulations such as topical gels or creams as an active ingredient, and as a chemical intermediate in the synthesis of sulfone derivatives and related functionalities in the chemical industry; additionally, dapsone is used as a research reagent in organic synthesis and the development of specialty chemicals.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.33
    methanol 53.74
    isopropanol 16.56
    water 0.17
    ethyl acetate 36.81
    n-propanol 18.17
    acetone 329.59
    n-butanol 5.89
    acetonitrile 110.92
    DMF 734.3
    toluene 0.46
    isobutanol 2.9
    1,4-dioxane 46.06
    methyl acetate 89.98
    THF 196.37
    2-butanone 163.74
    n-pentanol 3.4
    sec-butanol 4.85
    n-hexane 0.01
    ethylene glycol 14.6
    NMP 240.26
    cyclohexane 0.07
    DMSO 339.72
    n-butyl acetate 11.09
    n-octanol 1.33
    chloroform 1.82
    n-propyl acetate 13.7
    acetic acid 73.04
    dichloromethane 2.18
    cyclohexanone 108.9
    propylene glycol 30.31
    isopropyl acetate 13.71
    DMAc 434.65
    2-ethoxyethanol 41.31
    isopentanol 3.33
    n-heptane 0.07
    ethyl formate 47.76
    1,2-dichloroethane 3.82
    n-hexanol 3.44
    2-methoxyethanol 127.4
    isobutyl acetate 4.11
    tetrachloromethane 0.25
    n-pentyl acetate 5.86
    transcutol 57.27
    n-heptanol 2.57
    ethylbenzene 0.32
    MIBK 9.84
    2-propoxyethanol 30.58
    tert-butanol 10.64
    MTBE 4.66
    2-butoxyethanol 15.5
    propionic acid 34.93
    o-xylene 0.51
    formic acid 64.17
    diethyl ether 5.2
    m-xylene 0.33
    p-xylene 0.72
    chlorobenzene 2.18
    dimethyl carbonate 32.55
    n-octane 0.04
    formamide 410.66
    cyclopentanone 327.4
    2-pentanone 45.65
    anisole 7.35
    cyclopentyl methyl ether 8.75
    gamma-butyrolactone 270.46
    1-methoxy-2-propanol 66.62
    pyridine 41.54
    3-pentanone 29.44
    furfural 154.2
    n-dodecane 0.04
    diethylene glycol 36.86
    diisopropyl ether 0.64
    tert-amyl alcohol 5.41
    acetylacetone 89.45
    n-hexadecane 0.05
    acetophenone 16.05
    methyl propionate 43.32
    isopentyl acetate 7.9
    trichloroethylene 11.08
    n-nonanol 1.57
    cyclohexanol 3.85
    benzyl alcohol 7.83
    2-ethylhexanol 1.87
    isooctanol 1.81
    dipropyl ether 3.05
    1,2-dichlorobenzene 2.59
    ethyl lactate 16.51
    propylene carbonate 69.3
    n-methylformamide 322.76
    2-pentanol 2.4
    n-pentane 0.02
    1-propoxy-2-propanol 18.03
    1-methoxy-2-propyl acetate 24.93
    2-(2-methoxypropoxy) propanol 16.79
    mesitylene 0.31
    ε-caprolactone 56.64
    p-cymene 0.81
    epichlorohydrin 88.34
    1,1,1-trichloroethane 2.03
    2-aminoethanol 29.49
    morpholine-4-carbaldehyde 183.07
    sulfolane 214.81
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 28.63
    n-hexyl acetate 5.44
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 21.21
    sec-butyl acetate 6.23
    tert-butyl acetate 12.67
    decalin 0.04
    glycerin 66.08
    diglyme 54.1
    acrylic acid 48.73
    isopropyl myristate 2.52
    n-butyric acid 27.09
    acetyl acetate 24.45
    di(2-ethylhexyl) phthalate 4.94
    ethyl propionate 11.69
    nitromethane 549.25
    1,2-diethoxyethane 10.86
    benzonitrile 12.79
    trioctyl phosphate 3.1
    1-bromopropane 0.68
    gamma-valerolactone 327.37
    n-decanol 1.28
    triethyl phosphate 6.76
    4-methyl-2-pentanol 1.5
    propionitrile 26.11
    vinylene carbonate 60.18
    1,1,2-trichlorotrifluoroethane 67.38
    DMS 14.21
    cumene 0.29
    2-octanol 1.16
    2-hexanone 15.3
    octyl acetate 3.78
    limonene 1.22
    1,2-dimethoxyethane 74.76
    ethyl orthosilicate 5.26
    tributyl phosphate 4.0
    diacetone alcohol 28.92
    N,N-dimethylaniline 3.93
    acrylonitrile 65.71
    aniline 4.96
    1,3-propanediol 32.63
    bromobenzene 1.07
    dibromomethane 0.82
    1,1,2,2-tetrachloroethane 7.59
    2-methyl-cyclohexyl acetate 7.82
    tetrabutyl urea 7.01
    diisobutyl methanol 1.41
    2-phenylethanol 8.44
    styrene 0.55
    dioctyl adipate 6.72
    dimethyl sulfate 65.18
    ethyl butyrate 10.7
    methyl lactate 50.14
    butyl lactate 10.27
    diethyl carbonate 8.91
    propanediol butyl ether 14.06
    triethyl orthoformate 8.47
    p-tert-butyltoluene 0.81
    methyl 4-tert-butylbenzoate 13.58
    morpholine 77.19
    tert-butylamine 2.11
    n-dodecanol 0.99
    dimethoxymethane 106.21
    ethylene carbonate 40.1
    cyrene 34.54
    2-ethoxyethyl acetate 16.99
    2-ethylhexyl acetate 5.5
    1,2,4-trichlorobenzene 4.83
    4-methylpyridine 18.34
    dibutyl ether 1.61
    2,6-dimethyl-4-heptanol 1.41
    DEF 52.77
    dimethyl isosorbide 38.5
    tetrachloroethylene 3.9
    eugenol 14.53
    triacetin 18.27
    span 80 11.69
    1,4-butanediol 9.25
    1,1-dichloroethane 2.0
    2-methyl-1-pentanol 2.26
    methyl formate 194.97
    2-methyl-1-butanol 2.58
    n-decane 0.07
    butyronitrile 14.65
    3,7-dimethyl-1-octanol 1.52
    1-chlorooctane 0.36
    1-chlorotetradecane 0.2
    n-nonane 0.05
    undecane 0.05
    tert-butylcyclohexane 0.04
    cyclooctane 0.02
    cyclopentanol 11.87
    tetrahydropyran 18.93
    tert-amyl methyl ether 3.1
    2,5,8-trioxanonane 35.82
    1-hexene 0.13
    2-isopropoxyethanol 15.17
    2,2,2-trifluoroethanol 35.52
    methyl butyrate 19.74

    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