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Chemistry

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Also known as: 528-29-0, O-dinitrobenzene, 1,2-dinitrobenzol, Benzene, o-dinitro-, Ortho-dinitrobenzene, Benzene, 1,2-dinitro-
Molecular Formula
C6H4N2O4
Molecular Weight
168.11  g/mol
InChI Key
IZUKQUVSCNEFMJ-UHFFFAOYSA-N
FDA UNII
35XUO924Y0

1,2-Dinitrobenzene
1 2D Structure

1,2-Dinitrobenzene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,2-dinitrobenzene
2.1.2 InChI
InChI=1S/C6H4N2O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H
2.1.3 InChI Key
IZUKQUVSCNEFMJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
35XUO924Y0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. O-dinitrobenzene

2. Ortho-dinitrobenzene

2.3.2 Depositor-Supplied Synonyms

1. 528-29-0

2. O-dinitrobenzene

3. 1,2-dinitrobenzol

4. Benzene, O-dinitro-

5. Ortho-dinitrobenzene

6. Benzene, 1,2-dinitro-

7. 1,2-dinitro-benzene

8. 25154-54-5

9. Chebi:34053

10. 35xuo924y0

11. Nsc-60682

12. Dsstox_cid_4066

13. Dsstox_rid_77278

14. Dsstox_gsid_24066

15. Dinitrobenzene, O-

16. O-dintrobenzene

17. Cas-528-29-0

18. Ccris 3091

19. Hsdb 4486

20. Einecs 208-431-8

21. Nsc 60682

22. Unii-35xuo924y0

23. Ai3-15338

24. Wln: Wnr Bnw

25. Schembl22566

26. 1,2-dinitrobenzene, 97%

27. Ghl.pd_mitscher_leg0.923

28. Bidd:er0518

29. O-dinitrobenzene [mi]

30. Chembl168075

31. 1,2-dinitrobenzene, >=99%

32. Dtxsid4024066

33. Act12765

34. Nsc60682

35. Zinc4261808

36. Tox21_201580

37. Tox21_300418

38. Mfcd00007093

39. Stl453602

40. Td1044

41. Akos000120631

42. Gs-3201

43. 1,2-dinitrobenzene, Analytical Standard

44. Ncgc00164050-01

45. Ncgc00164050-02

46. Ncgc00164050-03

47. Ncgc00254393-01

48. Ncgc00259129-01

49. O-dinitrobenzene [un1597] [poison]

50. Ac-26090

51. D0818

52. Ft-0632304

53. En300-17305

54. A20874

55. J-200033

56. Q2238767

57. Z56914842

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 168.11 g/mol
Molecular Formula C6H4N2O4
XLogP31.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass168.01710661 g/mol
Monoisotopic Mass168.01710661 g/mol
Topological Polar Surface Area91.6 Ų
Heavy Atom Count12
Formal Charge0
Complexity173
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 Absorption, Distribution and Excretion

Readily absorbed through the skin, either as solid, liquid, or vapor. /Dinitrobenzene/

Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1


4.2 Metabolism/Metabolites

Nitroreductase activity was previously known to occur under nitrogen atmosphere in the cytosolic and microsomal fractions of liver homogenates. This study describes a subcellular nitroreductase activity which occurs in liver mitochondria under aerobic conditions. Mitochondria were isolated from rat liver and assayed for their capacity to reduce certain nitro compounds by measuring spectrophotometrically both the appearance of amino compounds and the consumption of nicotinamide adenine dinucleotide. Intact mitochondria were found to possess a p-dinitrobenzene reductase activity. The activity was destroyed by heat, and was present at only 20% in the microsomal fraction. It was strictly nicotinamide adenine dinucleotide-dependent, while only little or no activity occurred with reduced nicotinamide adenine dinucleotide or other oxidative substrates. Nitro reduction was inhibited by thiol reagents. Rat liver mitochondria showed about 15% activity with o-dinitrobenzene and m-dinitrobenzene, while there was less than 5% activity with a series of p-nitro compounds including chloramphenicol.

Abou-Khalil S et al; Pharmacology (Basal) 31 (6): 301-8 (1985)


The metabolism of radiolabeled dinitrobenzene isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male Fischer-344 rats. Under aerobic conditions, reduction was the major metabolic pathway for m- and p-dinitrobenzene in hepatocytes with m- and p-nitroaniline accounting for 74.0 + or - 1.2 and 81.0 + or - 0.6% (mean + or - SE, n= 4), respectively, of the radioactivity present after a 30 min incubation. The major metabolite of o-dinitrobenzene in similar incubations was S-(2-nitrophenyl)glutathione which represented 48.1 + or - 5.5% of the total radioactivity; o-nitroaniline accounted for 29.5 + or - 2.1% of the radioactivity. Incubation of dinitrobenzene with microsomes produced nitroanilines as well as nitrosonitrobenzenes and nitrophenylhydroxylamines. Reduction of o- and m-dinitrobenzene by microsomes was reduced nicotinamide adenine dinucleotide-dependent. Reduction of p-dinitrobenzene could be supported by nicotinamide adenine dinucleotide as well as reduced nicotinamide adenine dinucleotide, although the rate of reduction was slower with NADH. Conjugation of o- and p-dinitrobenzene, but not m-dinitrobenzene, with glutathione occurred in cytosol incubations although only o-dinitrobenzene formed the glutathione conjugate in intact hepatocytes.

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


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