4-Amino-1,8-naphthalimide

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  • Identifiers

    CAS number
    1742-95-6

    Molecular formula
    C12H8N2O2

    SMILES
    C1=CC2=C(C=CC3=C2C(=C1)C(=O)NC3=O)N

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 49.52%
    Bitter 28.38%
    Sweet 27.56%
    Grape 26.92%
    Fruity 25.84%
    Burnt 23.58%
    Phenolic 21.12%
    Musty 20.17%
    Animal 20.07%
    Neroli 19.02%

     

    Flavor
    Bitter 93.1%
    Odorless 30.46%
    Nitrile 19.91%
    Very strong 19.68%
    Indole 19.32%
    Sweet-like 18.52%
    Cedarleaf 18.51%
    Rotten 18.4%
    Lovage 18.23%
    Bread crust 18.07%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    7.16 (neutral)

    Molecular weight
    212.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    850°C

    Flash point

    • 265.7 ˚C est.

  • Synonyms

    • 4-Amino-1,8-naphthalimide
    • 1742-95-6
    • 4-Aminonaphthalimide
    • 6-AMINO-BENZO[DE]ISOQUINOLINE-1,3-DIONE
    • 6-aminobenzo[de]isoquinoline-1,3-dione
    • 4-Aminonaphthalene-1,8-dicarboximide
    • DFP 1
    • 4-amino1,8-naphthalimide
    • 6-Amino-1H-benz(de)isoquinoline-1,3(2H)-dione
    • S529AR2S8B
    • DTXSID6061941
    • CHEBI:40071
    • D-122
    • 6-AMINO-BENZO(DE)ISOQUINOLINE-1,3-DIONE
    • 6-aminobenzo(de)isoquinoline-1,3-dione
    • RefChem:517404
    • DTXCID3035559
    • 217-110-1
    • 6-Amino-1H-benzo[de]isoquinoline-1,3(2H)-dione
    • 1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino-
    • MFCD00006921
    • CHEMBL338790
    • 1H-Benz(de)isoquinoline-1,3(2H)-dione, 6-amino-
    • Naphthalimide, 4-amino-
    • EINECS 217-110-1
    • BRN 0177185
    • 2pax
    • Lopac-A-0966
    • 4-ANI
    • UNII-S529AR2S8B
    • Lopac0_000063
    • SCHEMBL21124
    • BSPBio_001430
    • KBioGR_000150
    • KBioSS_000150
    • 4-22-00-06603 (Beilstein Handbook Reference)
    • orb1306313
    • SCHEMBL29941362
    • BCBcMAP01_000231
    • BDBM27498
    • KBio2_000150
    • KBio2_002718
    • KBio2_005286
    • KBio3_000299
    • KBio3_000300
    • Bio1_000370
    • Bio1_000859
    • Bio1_001348
    • Bio2_000150
    • Bio2_000630
    • HMS1361H12
    • HMS1791H12
    • HMS1989H12
    • HMS3260M07
    • HMS3402H12
    • BB_SC-07136
    • 4-Amino-1,8-naphthalimide, 95%
    • 4-Amino-1,8-naphthalimide, 96%
    • 6-amino-1H-benz[de]isoquinoline-1
    • Tox21_500063
    • BBL027625
    • SBB003425
    • STK934866
    • AKOS005664748
    • CCG-204158
    • DB07096
    • FA67151
    • LP00063
    • SDCCGSBI-0050051.P002
    • IDI1_033900
    • NCGC00015035-01
    • NCGC00015035-02
    • NCGC00015035-03
    • NCGC00015035-04
    • NCGC00015035-05
    • NCGC00015035-06
    • NCGC00015035-07
    • NCGC00015035-08
    • NCGC00093577-01
    • NCGC00093577-02
    • NCGC00093577-03
    • NCGC00093577-04
    • NCGC00093577-05
    • NCGC00260748-01
    • 4AN
    • AS-35824
    • HY-15276
    • PD002801
    • SY257978
    • DB-043973
    • CS-0003831
    • EU-0100063
    • NS00019549
    • ST50825610
    • A 0966
    • 6-amino-1H-benz[de]-isoquinoline-1,3(2H)-dione
    • F040622
    • SR-01000075200
    • SR-01000075200-1
    • 6-Amino-1H-benzo[de]isoquinoline-1,3(2H)-dione #
    • Amino-1,8-naphthalimide [4-Amino-1,8-naphthalimide]
    • BRD-K50214219-001-02-4
    • Q27096011
    • 10-amino-3-azatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione
    • 1742-95-6

  • Applications

    Chemical name: 4-Amino-1,8-naphthalimide; CAS number: 1742-95-6. 4-Amino-1,8-naphthalimide and its derivatives are used as fluorescent dyes and probes in analytical chemistry and sensing applications, notably for metal-ion detection and other analytes. It also serves as a fluorescent emitter in organic electronics and as a dye component in coatings, inks, and specialty plastics. As an intermediate, it is a building block for the synthesis of dye and pigment products. It can be incorporated into polymer matrices to impart fluorescence and used as a chemosensor signal reporter in environmental or chemical sensing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.37
    methanol 0.68
    isopropanol 0.28
    water 0.02
    ethyl acetate 0.72
    n-propanol 0.32
    acetone 1.63
    n-butanol 0.31
    acetonitrile 0.88
    DMF 13.37
    toluene 0.2
    isobutanol 0.23
    1,4-dioxane 2.84
    methyl acetate 0.9
    THF 4.21
    2-butanone 1.06
    n-pentanol 0.39
    sec-butanol 0.16
    n-hexane 0.01
    ethylene glycol 0.82
    NMP 21.95
    cyclohexane 0.01
    DMSO 16.05
    n-butyl acetate 1.31
    n-octanol 0.67
    chloroform 0.27
    n-propyl acetate 0.8
    acetic acid 1.61
    dichloromethane 0.72
    cyclohexanone 2.8
    propylene glycol 0.4
    isopropyl acetate 0.69
    DMAc 12.4
    2-ethoxyethanol 1.94
    isopentanol 0.4
    n-heptane 0.04
    ethyl formate 1.25
    1,2-dichloroethane 0.72
    n-hexanol 0.68
    2-methoxyethanol 3.8
    isobutyl acetate 0.53
    tetrachloromethane 0.09
    n-pentyl acetate 1.62
    transcutol 3.54
    n-heptanol 0.93
    ethylbenzene 0.21
    MIBK 0.92
    2-propoxyethanol 4.06
    tert-butanol 0.46
    MTBE 0.15
    2-butoxyethanol 3.27
    propionic acid 0.77
    o-xylene 0.31
    formic acid 1.84
    diethyl ether 0.18
    m-xylene 0.31
    p-xylene 0.36
    chlorobenzene 0.54
    dimethyl carbonate 1.99
    n-octane 0.03
    formamide 3.61
    cyclopentanone 5.46
    2-pentanone 0.97
    anisole 0.92
    cyclopentyl methyl ether 0.79
    gamma-butyrolactone 7.57
    1-methoxy-2-propanol 2.38
    pyridine 2.75
    3-pentanone 0.7
    furfural 11.46
    n-dodecane 0.04
    diethylene glycol 5.39
    diisopropyl ether 0.1
    tert-amyl alcohol 0.25
    acetylacetone 3.07
    n-hexadecane 0.05
    acetophenone 2.26
    methyl propionate 1.11
    isopentyl acetate 1.41
    trichloroethylene 1.59
    n-nonanol 0.8
    cyclohexanol 0.32
    benzyl alcohol 1.37
    2-ethylhexanol 0.61
    isooctanol 0.87
    dipropyl ether 0.5
    1,2-dichlorobenzene 0.92
    ethyl lactate 1.51
    propylene carbonate 3.67
    n-methylformamide 3.83
    2-pentanol 0.16
    n-pentane 0.01
    1-propoxy-2-propanol 2.26
    1-methoxy-2-propyl acetate 3.09
    2-(2-methoxypropoxy) propanol 3.82
    mesitylene 0.26
    ε-caprolactone 2.94
    p-cymene 0.63
    epichlorohydrin 5.99
    1,1,1-trichloroethane 0.34
    2-aminoethanol 0.77
    morpholine-4-carbaldehyde 16.12
    sulfolane 16.51
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.15
    n-hexyl acetate 1.64
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 4.02
    sec-butyl acetate 0.52
    tert-butyl acetate 0.93
    decalin 0.03
    glycerin 2.08
    diglyme 7.34
    acrylic acid 1.53
    isopropyl myristate 1.02
    n-butyric acid 1.01
    acetyl acetate 1.13
    di(2-ethylhexyl) phthalate 2.38
    ethyl propionate 0.83
    nitromethane 5.62
    1,2-diethoxyethane 1.33
    benzonitrile 2.18
    trioctyl phosphate 1.72
    1-bromopropane 0.13
    gamma-valerolactone 11.68
    n-decanol 0.69
    triethyl phosphate 1.51
    4-methyl-2-pentanol 0.22
    propionitrile 0.72
    vinylene carbonate 3.82
    1,1,2-trichlorotrifluoroethane 6.26
    DMS 2.36
    cumene 0.27
    2-octanol 0.5
    2-hexanone 1.03
    octyl acetate 1.43
    limonene 0.59
    1,2-dimethoxyethane 4.12
    ethyl orthosilicate 1.3
    tributyl phosphate 1.41
    diacetone alcohol 2.23
    N,N-dimethylaniline 1.08
    acrylonitrile 1.78
    aniline 0.63
    1,3-propanediol 1.15
    bromobenzene 0.41
    dibromomethane 0.21
    1,1,2,2-tetrachloroethane 1.17
    2-methyl-cyclohexyl acetate 1.77
    tetrabutyl urea 2.95
    diisobutyl methanol 0.46
    2-phenylethanol 2.17
    styrene 0.22
    dioctyl adipate 2.0
    dimethyl sulfate 6.18
    ethyl butyrate 1.17
    methyl lactate 2.45
    butyl lactate 2.13
    diethyl carbonate 1.17
    propanediol butyl ether 2.33
    triethyl orthoformate 1.32
    p-tert-butyltoluene 0.5
    methyl 4-tert-butylbenzoate 4.57
    morpholine 2.59
    tert-butylamine 0.16
    n-dodecanol 0.57
    dimethoxymethane 4.77
    ethylene carbonate 2.65
    cyrene 7.4
    2-ethoxyethyl acetate 2.87
    2-ethylhexyl acetate 1.12
    1,2,4-trichlorobenzene 1.55
    4-methylpyridine 1.96
    dibutyl ether 0.47
    2,6-dimethyl-4-heptanol 0.46
    DEF 2.36
    dimethyl isosorbide 9.47
    tetrachloroethylene 0.83
    eugenol 4.95
    triacetin 3.03
    span 80 3.22
    1,4-butanediol 0.72
    1,1-dichloroethane 0.21
    2-methyl-1-pentanol 0.42
    methyl formate 3.42
    2-methyl-1-butanol 0.26
    n-decane 0.05
    butyronitrile 0.71
    3,7-dimethyl-1-octanol 0.68
    1-chlorooctane 0.28
    1-chlorotetradecane 0.19
    n-nonane 0.04
    undecane 0.05
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 0.61
    tetrahydropyran 0.59
    tert-amyl methyl ether 0.19
    2,5,8-trioxanonane 7.01
    1-hexene 0.04
    2-isopropoxyethanol 1.37
    2,2,2-trifluoroethanol 1.59
    methyl butyrate 1.15

    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