2,6-Pyridinedicarboxylic acid

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  • Identifiers

    CAS number
    499-83-2

    Molecular formula
    C7H5NO4

    SMILES
    C1=CC(=NC(=C1)C(=O)O)C(=O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 71.02%
    Sour 32.21%
    Burnt 30.64%
    Nutty 28.93%
    Roasted 27.17%
    Cooked 22.37%
    Caramellic 21.21%
    Savory 19.42%
    Bitter 19.24%
    Musty 18.75%

     

    Flavor
    Odorless 63.25%
    Nutty 49.63%
    Sour 36.67%
    Mild 36.16%
    Very mild 32.4%
    Faint 30.09%
    Phenolic 26.06%
    Musty 25.94%
    Bread 23.84%
    Caramellic 23.32%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    5.39 (weak acid)

    Molecular weight
    167.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    429°C

    Melting point expt.

    • 252 °C

    Flash point

    • 216.44 ˚C est.

    Solubility expt.

    • 5 mg/mL at 25 °C

  • Synonyms

    • 2,6-Pyridinedicarboxylic acid
    • 499-83-2
    • PYRIDINE-2,6-DICARBOXYLIC ACID
    • Dipicolinic acid
    • 2,6-Dipicolinic acid
    • 2,6-Dicarboxypyridine
    • UE81S5CQ0G
    • DTXSID7022043
    • NSC-176
    • DTXCID602043
    • CHEBI:46837
    • RefChem:134748
    • 207-894-3
    • Dipicolinate
    • MFCD00006299
    • DPAC
    • CHEMBL284104
    • 2,6-pyridine dicarboxylic acid
    • 2,6-Pyridinedicarboxylic acid, 99%
    • NSC 176
    • EINECS 207-894-3
    • UNII-UE81S5CQ0G
    • pyridine-2
    • pydcH2
    • 4ih3
    • pyridine carboxylate, 6d
    • pyridine, 2,6-dicarboxy-
    • Oprea1_533632
    • SCHEMBL34595
    • 2,6-DIPICLINIC ACID
    • MLS000080748
    • 6-CARBOXYPICOLINIC ACID
    • IFLab1_001781
    • NSC176
    • SCHEMBL3663998
    • SCHEMBL6511339
    • Dipicolinic acid, Beauveria sp.
    • BDBM26116
    • Pyridinedicarboxylic acid-(2,6)
    • HMS1417A21
    • HMS2231H20
    • BB_NC-02784
    • HY-Y1024
    • Tox21_301129
    • AC-704
    • BBL012080
    • CCG-44216
    • CL0252
    • EBC-03340
    • SBB028480
    • STK092939
    • PYRIDINE-2,6-DICARBOXYLICACID
    • AKOS000112829
    • DB04267
    • FP34525
    • PS-8736
    • NCGC00071864-02
    • NCGC00255028-01
    • CAS-499-83-2
    • SMR000034075
    • ST040658
    • SY001460
    • DB-015930
    • CS-0016012
    • EU-0033484
    • NS00013573
    • P0554
    • EN300-18133
    • F066072
    • Q417164
    • 2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid
    • SR-01000600024-2
    • W-105996
    • L-042,134
    • Z57202012
    • B63A70CE-B9AB-4EA2-834A-6C7634226BB0
    • F0451-0137
    • 2,6-Pyridinedicarboxylic acid, for ion chromatography, >=99.5% (T)
    • InChI=1/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12
    • 499-83-2

  • Applications

    Chemical name: 2,6-Pyridinedicarboxylic acid; CAS 499-83-2. It is primarily used as a chelating ligand for transition metals and as a building block in the synthesis of metal-organic frameworks (MOFs) and coordination polymers, where its two carboxylate groups and the pyridine nitrogen enable strong multidentate binding. It is commonly employed as a precursor or intermediate in ligand design and catalyst development, enabling the creation of bespoke catalysts and functional materials. In analytical and materials contexts, it serves as a ligand or probe in luminescent sensing and metal-ion detection, often for research applications. In industrial formulations, it may function as a chelating additive to sequester trace metal contaminants and stabilize metal-containing systems. As a specialized building block for advanced polymers and sensor materials, it supports the development of electronics- or optics-relevant materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 22.3
    methanol 35.87
    isopropanol 14.82
    water 1.03
    ethyl acetate 2.95
    n-propanol 14.8
    acetone 4.87
    n-butanol 8.76
    acetonitrile 1.58
    DMF 65.93
    toluene 2.82
    isobutanol 5.27
    1,4-dioxane 5.38
    methyl acetate 1.96
    THF 9.11
    2-butanone 4.28
    n-pentanol 5.98
    sec-butanol 7.49
    n-hexane 0.29
    ethylene glycol 23.35
    NMP 82.62
    cyclohexane 0.21
    DMSO 129.84
    n-butyl acetate 2.47
    n-octanol 8.84
    chloroform 0.24
    n-propyl acetate 1.03
    acetic acid 3.22
    dichloromethane 1.14
    cyclohexanone 4.02
    propylene glycol 16.75
    isopropyl acetate 1.49
    DMAc 61.27
    2-ethoxyethanol 22.41
    isopentanol 4.45
    n-heptane 1.13
    ethyl formate 3.01
    1,2-dichloroethane 2.25
    n-hexanol 5.16
    2-methoxyethanol 46.12
    isobutyl acetate 0.25
    tetrachloromethane 0.07
    n-pentyl acetate 4.18
    transcutol 40.5
    n-heptanol 9.46
    ethylbenzene 1.28
    MIBK 1.5
    2-propoxyethanol 20.36
    tert-butanol 7.63
    MTBE 2.38
    2-butoxyethanol 21.58
    propionic acid 4.49
    o-xylene 3.29
    formic acid 19.47
    diethyl ether 3.98
    m-xylene 2.71
    p-xylene 0.99
    chlorobenzene 0.65
    dimethyl carbonate 3.94
    n-octane 0.55
    formamide 29.44
    cyclopentanone 5.86
    2-pentanone 3.89
    anisole 2.63
    cyclopentyl methyl ether 4.07
    gamma-butyrolactone 9.42
    1-methoxy-2-propanol 31.1
    pyridine 8.35
    3-pentanone 2.98
    furfural 13.62
    n-dodecane 0.5
    diethylene glycol 25.32
    diisopropyl ether 0.95
    tert-amyl alcohol 5.13
    acetylacetone 3.3
    n-hexadecane 0.57
    acetophenone 3.38
    methyl propionate 5.47
    isopentyl acetate 1.66
    trichloroethylene 1.34
    n-nonanol 8.77
    cyclohexanol 3.53
    benzyl alcohol 5.11
    2-ethylhexanol 2.67
    isooctanol 5.67
    dipropyl ether 4.33
    1,2-dichlorobenzene 0.87
    ethyl lactate 3.16
    propylene carbonate 2.91
    n-methylformamide 27.69
    2-pentanol 4.9
    n-pentane 0.52
    1-propoxy-2-propanol 14.36
    1-methoxy-2-propyl acetate 6.05
    2-(2-methoxypropoxy) propanol 18.74
    mesitylene 1.64
    ε-caprolactone 5.12
    p-cymene 2.17
    epichlorohydrin 8.81
    1,1,1-trichloroethane 0.19
    2-aminoethanol 27.71
    morpholine-4-carbaldehyde 35.57
    sulfolane 29.2
    2,2,4-trimethylpentane 0.21
    2-methyltetrahydrofuran 4.52
    n-hexyl acetate 5.14
    isooctane 0.13
    2-(2-butoxyethoxy)ethanol 27.63
    sec-butyl acetate 0.54
    tert-butyl acetate 1.39
    decalin 0.2
    glycerin 29.03
    diglyme 27.4
    acrylic acid 5.81
    isopropyl myristate 2.5
    n-butyric acid 3.68
    acetyl acetate 0.84
    di(2-ethylhexyl) phthalate 4.42
    ethyl propionate 1.7
    nitromethane 6.15
    1,2-diethoxyethane 6.31
    benzonitrile 2.3
    trioctyl phosphate 3.67
    1-bromopropane 1.52
    gamma-valerolactone 14.58
    n-decanol 6.94
    triethyl phosphate 1.61
    4-methyl-2-pentanol 1.96
    propionitrile 2.43
    vinylene carbonate 2.91
    1,1,2-trichlorotrifluoroethane 10.25
    DMS 2.92
    cumene 0.92
    2-octanol 5.3
    2-hexanone 1.43
    octyl acetate 4.22
    limonene 2.45
    1,2-dimethoxyethane 12.19
    ethyl orthosilicate 1.55
    tributyl phosphate 2.27
    diacetone alcohol 5.57
    N,N-dimethylaniline 4.45
    acrylonitrile 4.36
    aniline 4.7
    1,3-propanediol 20.66
    bromobenzene 0.51
    dibromomethane 0.68
    1,1,2,2-tetrachloroethane 1.62
    2-methyl-cyclohexyl acetate 1.61
    tetrabutyl urea 7.44
    diisobutyl methanol 2.16
    2-phenylethanol 4.83
    styrene 1.08
    dioctyl adipate 4.22
    dimethyl sulfate 9.93
    ethyl butyrate 2.11
    methyl lactate 12.01
    butyl lactate 6.27
    diethyl carbonate 1.26
    propanediol butyl ether 19.03
    triethyl orthoformate 2.12
    p-tert-butyltoluene 2.02
    methyl 4-tert-butylbenzoate 11.66
    morpholine 11.81
    tert-butylamine 3.61
    n-dodecanol 4.79
    dimethoxymethane 27.86
    ethylene carbonate 1.99
    cyrene 15.76
    2-ethoxyethyl acetate 6.78
    2-ethylhexyl acetate 1.32
    1,2,4-trichlorobenzene 1.3
    4-methylpyridine 6.26
    dibutyl ether 2.98
    2,6-dimethyl-4-heptanol 2.16
    DEF 13.38
    dimethyl isosorbide 17.47
    tetrachloroethylene 1.16
    eugenol 12.91
    triacetin 5.43
    span 80 15.15
    1,4-butanediol 9.39
    1,1-dichloroethane 0.5
    2-methyl-1-pentanol 2.94
    methyl formate 11.17
    2-methyl-1-butanol 4.57
    n-decane 0.8
    butyronitrile 2.23
    3,7-dimethyl-1-octanol 4.45
    1-chlorooctane 2.15
    1-chlorotetradecane 1.02
    n-nonane 0.71
    undecane 0.65
    tert-butylcyclohexane 0.15
    cyclooctane 0.24
    cyclopentanol 4.44
    tetrahydropyran 3.01
    tert-amyl methyl ether 2.73
    2,5,8-trioxanonane 28.3
    1-hexene 0.86
    2-isopropoxyethanol 8.1
    2,2,2-trifluoroethanol 2.11
    methyl butyrate 1.74

    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