4,4'-(1,3,6,8-Tetrahydro-1,3,6,8-tetraoxobenzo(lmn)(3,8)phenanthroline-2,7-diyl)bisbenzoic acid, diethyl ester

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  • Identifiers

    CAS number
    132459-54-2

    Molecular formula
    C32H22N2O8

    SMILES
    CCOC(=O)C1=CC=C(C=C1)N2C(=O)C3=C4C(=CC=C5C4=C(C=C3)C(=O)N(C5=O)C6=CC=C(C=C6)C(=O)OCC)C2=O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 44.59%
    Grape 44.41%
    Fruity 41.82%
    Floral 39.81%
    Neroli 32.21%
    Sweet 29.62%
    Powdery 25.7%
    Winey 24.28%
    Orange 24.15%
    Bitter 23.31%

     

    Flavor
    Bitter 95.23%
    Odorless 30.6%
    Bland 22.29%
    Sweet-like 18.88%
    Nitrile 18.39%
    Lovage 18.2%
    Cedarleaf 18.03%
    Very strong 17.52%
    Aniseed 17.49%
    Indole 17.47%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    4.7

    pKa est.
    3.48 (weak acid)

    Molecular weight
    562.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    578°C

    Flash point

    • 335.76 ˚C est.

  • Synonyms

    • UNII-EFV8379BUK
    • EFV8379BUK
    • 132459-54-2
    • Benzo(lmn)(3,8)phenanthroline, benzoic acid deriv.
    • 4,4'-(1,3,6,8-Tetrahydro-1,3,6,8-tetraoxobenzo(lmn)(3,8)phenanthroline-2,7-diyl)bisbenzoic acid, diethyl ester
    • Benzoic acid, 4,4'-(1,3,6,8-tetrahydro-1,3,6,8-tetraoxobenzo(lmn)(3,8)phenanthroline-2,7-diyl)bis-, diethyl ester
    • VJGZSQFTKVTZJM-UHFFFAOYSA-N
    • DTXSID001022029
    • NS00097014
    • AG-205/32561061
    • Q27277149
    • N,N'-Bis[4-(ethoxycarbonyl)phenyl]-1,4,5,8-naphthalenetetracarboxydiimide
    • DIETHYL N,N'-BIS(CARBOXYPHENYL)-1,4,5,8-NAPHTHALENETETRACARBOXYDIIMIDE
    • diethyl ester4,4'-(1,3,6,8-tetrahydro-1,3,6,8-tetraoxobenzo(lmn)(3,8)phenanthroline-2,7-diyl)bisbenzoic acid
    • 132459-54-2

  • Applications

    4,4'-(1,3,6,8-Tetrahydro-1,3,6,8-tetraoxobenzo(lmn)(3,8)phenanthroline-2,7-diyl)bisbenzoic acid, diethyl ester (CAS 132459-54-2) is primarily used as a ligand and precursor in metal coordination chemistry, enabling chelating complexes for catalysis and synthetic transformations; it serves as a building block for metal–organic frameworks (MOFs) and other coordination polymers, supporting applications in separations, sensing, and functional materials; the presence of the phenanthroline motif and ester groups allows hydrolysis to the corresponding diacid and conversion to ligands with different solubilities, expanding its role in ligand design and catalyst systems; due to its extended aromatic core, it is evaluated for optoelectronic and sensor applications where metal complexes of phenanthroline-based ligands are exploited; overall, it is commonly considered a versatile precursor for ligand synthesis in industrial and academic settings, with use cases spanning catalysis, materials science, and chemical sensing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.2
    methanol 0.27
    isopropanol 0.14
    water 0.0
    ethyl acetate 0.57
    n-propanol 0.22
    acetone 1.08
    n-butanol 0.18
    acetonitrile 0.5
    DMF 3.04
    toluene 0.38
    isobutanol 0.15
    1,4-dioxane 1.68
    methyl acetate 1.07
    THF 1.81
    2-butanone 1.66
    n-pentanol 0.2
    sec-butanol 0.17
    n-hexane 0.01
    ethylene glycol 0.12
    NMP 5.67
    cyclohexane 0.01
    DMSO 2.0
    n-butyl acetate 0.68
    n-octanol 0.16
    chloroform 1.55
    n-propyl acetate 0.64
    acetic acid 0.65
    dichloromethane 1.85
    cyclohexanone 2.92
    propylene glycol 0.09
    isopropyl acetate 0.35
    DMAc 6.31
    2-ethoxyethanol 0.89
    isopentanol 0.14
    n-heptane 0.01
    ethyl formate 0.79
    1,2-dichloroethane 1.18
    n-hexanol 0.12
    2-methoxyethanol 1.04
    isobutyl acetate 0.31
    tetrachloromethane 0.17
    n-pentyl acetate 0.81
    transcutol 1.28
    n-heptanol 0.17
    ethylbenzene 0.16
    MIBK 0.38
    2-propoxyethanol 0.95
    tert-butanol 0.11
    MTBE 0.14
    2-butoxyethanol 0.85
    propionic acid 0.59
    o-xylene 0.24
    formic acid 0.62
    diethyl ether 0.23
    m-xylene 0.17
    p-xylene 0.28
    chlorobenzene 0.64
    dimethyl carbonate 0.68
    n-octane 0.01
    formamide 1.13
    cyclopentanone 3.23
    2-pentanone 0.82
    anisole 0.32
    cyclopentyl methyl ether 0.37
    gamma-butyrolactone 3.54
    1-methoxy-2-propanol 0.5
    pyridine 3.04
    3-pentanone 0.89
    furfural 3.95
    n-dodecane 0.01
    diethylene glycol 0.79
    diisopropyl ether 0.04
    tert-amyl alcohol 0.14
    acetylacetone 1.1
    n-hexadecane 0.01
    acetophenone 0.94
    methyl propionate 0.83
    isopentyl acetate 0.52
    trichloroethylene 2.81
    n-nonanol 0.19
    cyclohexanol 0.2
    benzyl alcohol 0.65
    2-ethylhexanol 0.1
    isooctanol 0.14
    dipropyl ether 0.19
    1,2-dichlorobenzene 0.58
    ethyl lactate 0.46
    propylene carbonate 1.17
    n-methylformamide 1.47
    2-pentanol 0.09
    n-pentane 0.01
    1-propoxy-2-propanol 0.52
    1-methoxy-2-propyl acetate 0.84
    2-(2-methoxypropoxy) propanol 0.88
    mesitylene 0.08
    ε-caprolactone 2.24
    p-cymene 0.1
    epichlorohydrin 3.05
    1,1,1-trichloroethane 0.49
    2-aminoethanol 0.18
    morpholine-4-carbaldehyde 4.57
    sulfolane 3.93
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.77
    n-hexyl acetate 0.58
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 1.02
    sec-butyl acetate 0.34
    tert-butyl acetate 0.27
    decalin 0.01
    glycerin 0.28
    diglyme 2.07
    acrylic acid 0.87
    isopropyl myristate 0.26
    n-butyric acid 0.53
    acetyl acetate 0.39
    di(2-ethylhexyl) phthalate 0.54
    ethyl propionate 0.52
    nitromethane 2.08
    1,2-diethoxyethane 0.81
    benzonitrile 1.19
    trioctyl phosphate 0.31
    1-bromopropane 0.37
    gamma-valerolactone 6.04
    n-decanol 0.14
    triethyl phosphate 0.42
    4-methyl-2-pentanol 0.05
    propionitrile 0.61
    vinylene carbonate 1.66
    1,1,2-trichlorotrifluoroethane 3.11
    DMS 0.95
    cumene 0.1
    2-octanol 0.13
    2-hexanone 0.87
    octyl acetate 0.38
    limonene 0.11
    1,2-dimethoxyethane 1.85
    ethyl orthosilicate 0.33
    tributyl phosphate 0.38
    diacetone alcohol 0.51
    N,N-dimethylaniline 0.26
    acrylonitrile 1.26
    aniline 0.51
    1,3-propanediol 0.35
    bromobenzene 0.52
    dibromomethane 0.82
    1,1,2,2-tetrachloroethane 1.88
    2-methyl-cyclohexyl acetate 0.43
    tetrabutyl urea 0.86
    diisobutyl methanol 0.06
    2-phenylethanol 0.53
    styrene 0.2
    dioctyl adipate 0.53
    dimethyl sulfate 1.3
    ethyl butyrate 0.52
    methyl lactate 0.56
    butyl lactate 0.68
    diethyl carbonate 0.41
    propanediol butyl ether 0.45
    triethyl orthoformate 0.47
    p-tert-butyltoluene 0.08
    methyl 4-tert-butylbenzoate 0.82
    morpholine 1.53
    tert-butylamine 0.05
    n-dodecanol 0.11
    dimethoxymethane 1.01
    ethylene carbonate 1.23
    cyrene 1.38
    2-ethoxyethyl acetate 1.43
    2-ethylhexyl acetate 0.49
    1,2,4-trichlorobenzene 0.94
    4-methylpyridine 1.94
    dibutyl ether 0.25
    2,6-dimethyl-4-heptanol 0.06
    DEF 1.52
    dimethyl isosorbide 1.53
    tetrachloroethylene 1.45
    eugenol 1.01
    triacetin 0.9
    span 80 0.64
    1,4-butanediol 0.21
    1,1-dichloroethane 0.58
    2-methyl-1-pentanol 0.19
    methyl formate 1.26
    2-methyl-1-butanol 0.16
    n-decane 0.02
    butyronitrile 0.46
    3,7-dimethyl-1-octanol 0.11
    1-chlorooctane 0.1
    1-chlorotetradecane 0.05
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.3
    tetrahydropyran 0.63
    tert-amyl methyl ether 0.15
    2,5,8-trioxanonane 1.61
    1-hexene 0.07
    2-isopropoxyethanol 0.53
    2,2,2-trifluoroethanol 0.63
    methyl butyrate 0.77

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
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Rinse-off products applied to the hair with some hand contact
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Category 2
Products applied to the axillae
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Leave-on products applied to the hair with some hand contact
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Category 3
Products applied to the face/body using fingertips
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Products with significant anogenital exposure
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Category 4
Products related to fine fragrance
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Products with body and hand exposure, primarily rinse off
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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
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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
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Category 5D
Baby Creams, baby Oils and baby talc
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Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
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Category 6
Products with oral and lip exposure
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Products not intended for direct skin contact, minimal or insignificant transfer to skin
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