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

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 Depositor-Supplied Synonyms

1. Hydrazobenzene

2. 122-66-7

3. 1,2-diphenyldiazane

4. Hydrazine, 1,2-diphenyl-

5. N,n'-bianiline

6. N,n'-diphenylhydrazine

7. Hydrazobenzen

8. Benzene, Hydrazodi-

9. (sym)-diphenylhydrazine

10. Rcra Waste Number U109

11. Nci-c01854

12. Hydrazine, Diphenyl-

13. Benzene, 1,1'-hydrazobis-

14. Hydrazobenzen [czech]

15. Diphenylhydrazine

16. 1,1'-hydrazodibenzene

17. Unii-1g3cs09tuk

18. Nsc 3510

19. Ccris 337

20. Symmetrical Diphenyl Hydrazine

21. Hsdb 2882

22. Einecs 204-563-5

23. Brn 0639793

24. 1g3cs09tuk

25. Ai3-15365

26. Ybqzxxmejhzymb-uhfffaoysa-n

27. Dsstox_cid_710

28. Dsstox_rid_75751

29. Dsstox_gsid_20710

30. 38622-18-3

31. Cas-122-66-7

32. Diphenylhydrazine, 1,2-

33. Hydrazobenzol

34. Hydrazodibenzene

35. 1,2-diphenyldrazine

36. Hydrazine,2-diphenyl-

37. Pubchem16518

38. Acmc-209alo

39. 1,2-diphenyl-hydrazine

40. Benzene,1'-hydrazobis-

41. Wln: Rmmr

42. Sym-diphenylhydrazine

43. Mr-ii-10

44. Schembl51179

45. 4-15-00-00056 (beilstein Handbook Reference)

46. 1,2-diphenylhydrazine (9ci)

47. Ac1l1l67

48. Chembl558459

49. Dtxsid7020710

50. Ctk3j2883

51. Ybqzxxmejhzymb-uhfffaoysa-

52. Nsc3510

53. Molport-001-783-357

54. Bdbm233141

55. Nsc-3510

56. Zinc1666823

57. Tox21_202323

58. Tox21_300492

59. Anw-18010

60. Ls-670

61. Sbb058764

62. Stl283944

63. Akos015889796

64. Mcule-4832667531

65. Rp24472

66. Ncgc00091240-01

67. Ncgc00091240-02

68. Ncgc00091240-03

69. Ncgc00091240-04

70. Ncgc00254433-01

71. Ncgc00259872-01

72. Aj-29044

73. An-43444

74. Cj-26992

75. H567

76. Db-005623

77. Kb-149247

78. Rt-001104

79. Ft-0082394

80. Ft-0600571

81. Ft-0629583

82. St24036730

83. St50826965

84. 1,2-diphenyldiazane (1,2-diphenylhydrazine)

85. Ks-00001467

86. 1,2-diphenylhydrazine, Remainder Mainly Azobenzene

87. A804943

88. I01-3081

89. W-108426

90. F0001-0358

91. 1,2-diphenylhydrazine, Analytical Standard, Ampule Of 100 Mg

92. Inchi=1/c12h12n2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14h

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 184.242 g/mol
Molecular Formula C12H12N2
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass184.1 g/mol
Monoisotopic Mass184.1 g/mol
Topological Polar Surface Area24.1 A^2
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 Pharmacology

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)


4.2 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/

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


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