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Also known as: Hydrazobenzene, 122-66-7, 1,2-diphenyldiazane, N,n'-bianiline, N,n'-diphenylhydrazine, Hydrazobenzen
Molecular Formula
C12H12N2
Molecular Weight
184.24  g/mol
InChI Key
YBQZXXMEJHZYMB-UHFFFAOYSA-N
FDA UNII
1G3CS09TUK

CAS 122-66-7
Hydrazobenzene is a colorless, crystalline compound that emits toxic fumes of nitrogen oxides when heated to decomposition. Hydrazobenzene has been used primarily in the dye manufacturing industry as the precursor of the dye intermediate benzidine and is also used as an intermediate in the manufacture of pharmaceuticals. Exposure to this substance irritates the skin, nose, throat and lungs and can eventually lead to liver, kidney and brain damage. Hydrazobenzene is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. (NCI05)
1 2D Structure

CAS 122-66-7

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,2-diphenylhydrazine
2.1.2 InChI
InChI=1S/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H
2.1.3 InChI Key
YBQZXXMEJHZYMB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)NNC2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
1G3CS09TUK
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hydrazobenzene

2.3.2 Depositor-Supplied Synonyms

1. Hydrazobenzene

2. 122-66-7

3. 1,2-diphenyldiazane

4. N,n'-bianiline

5. N,n'-diphenylhydrazine

6. Hydrazobenzen

7. Benzene, Hydrazodi-

8. Hydrazine, 1,2-diphenyl-

9. (sym)-diphenylhydrazine

10. Rcra Waste Number U109

11. Nci-c01854

12. Benzene, 1,1'-hydrazobis-

13. Diphenylhydrazine

14. Nsc 3510

15. 1g3cs09tuk

16. 1,2-diphenylhydrazine (9ci)

17. Nsc-3510

18. 38622-18-3

19. Dsstox_cid_710

20. Dsstox_rid_75751

21. Dsstox_gsid_20710

22. Hydrazobenzen [czech]

23. 1,1'-hydrazodibenzene

24. Diphenylhydrazine, 1,2-

25. Cas-122-66-7

26. Symmetrical Diphenyl Hydrazine

27. Ccris 337

28. Hydrazine, Diphenyl-

29. 1,2-diphenyldiazane (1,2-diphenylhydrazine)

30. Hsdb 2882

31. Einecs 204-563-5

32. Unii-1g3cs09tuk

33. Brn 0639793

34. Hydrazobenzol

35. Ai3-15365

36. Hydrazine,2-diphenyl-

37. N,n'-biphenylhydrazine

38. 1,2-diphenyl-hydrazine

39. Benzene,1'-hydrazobis-

40. Wln: Rmmr

41. Mr-ii-10

42. Schembl51179

43. Hydrazobenzene [hsdb]

44. 4-15-00-00056 (beilstein Handbook Reference)

45. Chembl558459

46. Dtxsid7020710

47. Ybqzxxmejhzymb-uhfffaoysa-

48. Nsc3510

49. Bdbm233141

50. Zinc1666823

51. Tox21_202323

52. Tox21_300492

53. Mfcd00003012

54. Stl283944

55. Akos015889796

56. Ncgc00091240-01

57. Ncgc00091240-02

58. Ncgc00091240-03

59. Ncgc00091240-04

60. Ncgc00254433-01

61. Ncgc00259872-01

62. Db-005623

63. Ft-0600571

64. Ft-0629583

65. H0180

66. F15405

67. Phenylbutazone Impurity C [ep Impurity]

68. A804943

69. Q424993

70. W-108426

71. 1,2-diphenylhydrazine, Analytical Standard, Ampule Of 100 Mg

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 184.24 g/mol
Molecular Formula C12H12N2
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass184.100048391 g/mol
Monoisotopic Mass184.100048391 g/mol
Topological Polar Surface Area24.1 Ų
Heavy Atom Count14
Formal Charge0
Complexity128
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

Thin layer chromatographic analysis of the urine of rats given an oral dose of 200 or 400 mg/kg revealed the presence of hydrazobenzene, benzidine, and two other unidentified metabolites. At an ip dose of 100 or 200 mg/kg, hydrazobenzene, aniline, benzidine, p-aminophenol, and o-aminophenol were identified in the urine. After iv or intratracheal administration of hydrazobenzene, only one urinary metabolite, which appeared to be phenolic, was found.

USEPA; Chemical Hazard Information Profile: Hydrazobenzene (Draft) p.6 (1981)


In the stomach, 1,2-diphenylhydrazine can be converted into benzidine, a known human carcinogen.

USEPA; Ambient Water Quality Criteria Doc: Diphenylhydrazine p.A-1 (1980) EPA 440/5-80-062


The enzyme systems in rat liver and lung responsible for the oxidative metabolism of hydrazine derivatives were studied to determine whether these enzymes, cytochrome P450 and monoamine oxidase, were responsible for metabolically activating hydrazines to carcinogenic/toxic metabolites. Cytochrome P450 preferentially oxidized the nitrogen to nitrogen bond of 1,2-disubstituted hydrazines and hydrazides, while monoamine oxidase oxidized the nitrogen to nitrogen bond of all the classes of hydrazine derivatives that were tested. Oxidation of the nitrogen to nitrogen bond led to the formation of stable azo intemediates in the case of 1,2-disubstituted hydrazines and to unstable monoazo (diazene) metabolites in the case of monosubstituted hydrazines and hydrazides. /Substituted hydrazines/

PMID:3271870 Erikson JM, Prough RA; J Biochem Toxicol 1 (1): 41-52 (1986)


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