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    CAS-88-74-4

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    2D Structure
    Also known as: O-nitroaniline, 88-74-4, 2-nitrobenzenamine, Benzenamine, 2-nitro-, O-nitraniline, 1-amino-2-nitrobenzene
    Molecular Formula
    C6H6N2O2
    Molecular Weight
    138.12  g/mol
    InChI Key
    DPJCXCZTLWNFOH-UHFFFAOYSA-N
    FDA UNII
    2519U0541L
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-nitroaniline
    2.1.2 InChI
    InChI=1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2
    2.1.3 InChI Key
    DPJCXCZTLWNFOH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C(=C1)N)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    2519U0541L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. O-nitroaniline

    2. Ortho-nitroaniline

    2.3.2 Depositor-Supplied Synonyms

    1. O-nitroaniline

    2. 88-74-4

    3. 2-nitrobenzenamine

    4. Benzenamine, 2-nitro-

    5. O-nitraniline

    6. 1-amino-2-nitrobenzene

    7. Devol Orange B

    8. Orange Grs Salt

    9. O-aminonitrobenzene

    10. 2-aminonitrobenzene

    11. Aniline, O-nitro-

    12. Azoic Diazo Component 6

    13. Fast Orange O Base

    14. Fast Orange O Salt

    15. Devol Orange Salt B

    16. Orthonitroaniline

    17. Fast Orange Base Gr

    18. Fast Orange Base Jr

    19. Fast Orange Gr Base

    20. Fast Orange Gr Salt

    21. Fast Orange Salt Gr

    22. Fast Orange Salt Jr

    23. Orange Base Ciba Ii

    24. Orange Base Irga Ii

    25. Orange Salt Ciba Ii

    26. Orange Salt Irga Ii

    27. Diazo Fast Orange Gr

    28. Ortho-nitroaniline

    29. Azoene Fast Orange Gr Salt

    30. Azofix Orange Gr Salt

    31. Azogene Fast Orange Gr

    32. Hindasol Orange Gr Salt

    33. 2-nitro-phenylamine

    34. Azoene Fast Orange Gr Base

    35. O-nitro Aniline

    36. Natasol Fast Orange Gr Salt

    37. Hiltonil Fast Orange Gr Base

    38. Hiltosal Fast Orange Gr Salt

    39. Brentamine Fast Orange Gr Base

    40. Brentamine Fast Orange Gr Salt

    41. C.i. Azoic Diazo Component 6

    42. Nsc 9796

    43. C.i. 37025

    44. 2-nitro-aniline

    45. Ona

    46. Dtxsid1025726

    47. Nsc-9796

    48. 2519u0541l

    49. Dsstox_cid_5726

    50. Dsstox_rid_77895

    51. Dsstox_gsid_25726

    52. Devol Orange B Diazo Fast Orange Gr

    53. Cas-88-74-4

    54. Ci Azoic Diazo Component 6

    55. Ccris 2317

    56. Hsdb 1132

    57. Einecs 201-855-4

    58. Ci 37025

    59. 2nitroaniline

    60. O-nitranilin

    61. O-nitro-aniline

    62. Ai3-02916

    63. 2-nitro Aniline

    64. 2-nitro-anilin

    65. Unii-2519u0541l

    66. 2-nitro-benzeneamine

    67. (2-nitrophenyl)-amine

    68. 1-nitro-2-aminobenzene

    69. 2-nitroaniline, 98%

    70. 2-nitroaniline, 99%

    71. 2-nitroaniline-al-14c

    72. (2-nitro-phenyl)-amine

    73. Nitroaniline, O-

    74. Wln: Zr Bnw

    75. Ortho Nitro Aniline

    76. Ec 201-855-4

    77. Schembl6000

    78. O-nitroaniline [mi]

    79. 2-nitroaniline [hsdb]

    80. Chembl274009

    81. Schembl11911292

    82. Nsc9796

    83. 2-nitroaniline, Analytical Standard

    84. Bcp05324

    85. Str00840

    86. Zinc3860642

    87. Tox21_202371

    88. Tox21_303292

    89. Bdbm50554334

    90. Mfcd00007687

    91. Stl140693

    92. Akos000119116

    93. Am87359

    94. O-nitroaniline [un1661] [poison]

    95. Ncgc00091373-01

    96. Ncgc00091373-02

    97. Ncgc00257171-01

    98. Ncgc00259920-01

    99. Bp-21264

    100. Db-057102

    101. 2-iminocyclohexa-3,5-diene-1-nitronic Acid

    102. 2-nitroaniline 1000 Microg/ml In Methanol

    103. Ft-0613173

    104. N0118

    105. 2-nitroaniline 100 Microg/ml In Acetonitrile

    106. D97708

    107. Q-201516

    108. Q2590230

    109. F2190-0432

    110. 38500-40-2

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 138.12 g/mol
    Molecular Formula C6H6N2O2
    XLogP31.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass138.042927438 g/mol
    Monoisotopic Mass138.042927438 g/mol
    Topological Polar Surface Area71.8 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity132
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Metabolism/Metabolites

    The metabolism of radiolabeled dinitrobenzene isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male rats. Under aerobic conditions, reduction was the major metabolic pathway for m-dinitrobenzene and p-dinitrobenzene in hepatocytes with m-nitroaniline and p-nitroaniline accounting for 74.0 and 81.0% respectively, of the radioactivity present after a 30 min incubation. The major metabolite of o-nitrobenzene in similar incubations was S-(2-nitrophenyl)glutathione which represented 48.1% of the total radioactivity. o-Nitroaniline accounted for 29.5% of the radioactivity.

    PMID:2867868 Cossum PA, Rickert DE; Drug Metab Dispos 13 (6): 664-8 (1985)

    4.2 Mechanism of Action

    THE RELATIVE MUTAGENIC ACTIVITIES OF AMINOANILINES HAVE BEEN ATTEMPTED TO BE RELATED TO PARAMETERS REFLECTING POTENTIAL FOR N-HYDROXYLATION AND STABILITY OF THE ARYLNITRENIUM IONS. THE NITRO GROUPS DEACTIVATE THE AMINE GROUP N-HYDROXYLATION AND THE EPOXIDATION, & NO ACTIVE PRODUCTS FROM CYTOCHROME P450 WOULD BE PREDICTED. THE ACTIVITY OF THE NITRO DERIVATIVES IS PRESUMED TO BE DUE TO TRANSFORMATION OF THE NITRO GROUP ITSELF TO AN ACTIVE MUTAGENIC SPECIES BY OTHER ENZYME SYSTEMS. /AMINOANILINES/

    PMID:448254 LOEW GH ET AL; J ENVIRON PATHOL TOXICOL 2 (4): 1069-78 (1979)