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CAS 88-74-4

CAS 88-74-4

Chemistry

Chemistry

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1 Intermediates

1 Intermediates

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

CAS 88-74-4

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 Formula	C₆H₆N₂O₂
Molecular Weight	138.12 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	138.042927438 g/mol
Monoisotopic Mass	138.042927438 g/mol
Topological Polar Surface Area	71.8 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	132
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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)