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Also known as: 554-00-7, Benzenamine, 2,4-dichloro-, 2,4-dichlorobenzenamine, 2,4-dichloranilin, O,p-dichloroaniline, Aniline, 2,4-dichloro-
Molecular Formula
C6H5Cl2N
Molecular Weight
162.01  g/mol
InChI Key
KQCMTOWTPBNWDB-UHFFFAOYSA-N
FDA UNII
19AE42M6WS

CAS 554-00-7
RN given refers to parent cpd
1 2D Structure

CAS 554-00-7

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,4-dichloroaniline
2.1.2 InChI
InChI=1S/C6H5Cl2N/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2
2.1.3 InChI Key
KQCMTOWTPBNWDB-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
19AE42M6WS
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 554-00-7

2. Benzenamine, 2,4-dichloro-

3. 2,4-dichlorobenzenamine

4. 2,4-dichloranilin

5. O,p-dichloroaniline

6. Aniline, 2,4-dichloro-

7. 2,4-dca

8. 1-amino-2,4-dichlorobenzene

9. 2,4-dichlorophenylamine

10. 19ae42m6ws

11. Dtxsid1024966

12. Nsc-8756

13. Dtxcid404966

14. Chebi:46635

15. Refchem:443431

16. 209-057-8

17. Mfcd00007661

18. 2,4-dichloro Aniline

19. 2,4-dichloro-phenylamine

20. Cas-554-00-7

21. 2,4-dichloranilin [german]

22. Ccris 6012

23. Hsdb 5428

24. Nsc 8756

25. Einecs 209-057-8

26. 2,4-dichlorobenzene Aniline

27. Brn 0386422

28. Unii-19ae42m6ws

29. 2,4-dichloraniline

30. 2,4-dichloroanilin

31. Clonidine Impurity 4

32. 2,4-di-chloroaniline

33. 2,4-dichloro-aniline

34. Wln: Zr Bg Dg

35. Ec 209-057-8

36. 2,4dichloro Aniline

37. 2,4-dichloroaniline, 99%

38. 4-12-00-01241 (beilstein Handbook Reference)

39. Bidd:er0533

40. Schembl158279

41. Schembl660048

42. Schembl1358936

43. Schembl3118468

44. Schembl6381071

45. Schembl6790265

46. Dichloroaniline, 2,4-

47. Chembl1528820

48. Schembl29732941

49. Nsc8756

50. 2,4-dichloroaniline [hsdb]

51. Tox21_201522

52. Tox21_303206

53. Msk1259-100t

54. Sbb007569

55. Stl168887

56. Akos000118881

57. Msk1259-1000t

58. Ccg-302558

59. Fd36980

60. Ps-6249

61. Rp10174

62. Ncgc00091375-01

63. Ncgc00091375-02

64. Ncgc00091375-03

65. Ncgc00257110-01

66. Ncgc00259072-01

67. 2,4-dichloroaniline, >=97.0% (gc)

68. Ac-10180

69. Db-030787

70. D0321

71. Ns00009494

72. St45255273

73. En300-18059

74. 2,4-dichloroaniline 100 Microg/ml In Methanol

75. F022088

76. 2,4-dichloroaniline Solution In Toluene, 100ug/ml

77. Q3102438

78. 2,4-dichloroaniline Solution In Toluene, 1000ug/ml

79. Z57127562

80. 2,4-dichloroaniline, Pestanal(r), Analytical Standard

81. F2190-0455

82. Inchi=1/c6h5cl2n/c7-4-1-2-6(9)5(8)3-4/h1-3h,9h

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 162.01 g/mol
Molecular Formula C6H5Cl2N
XLogP32.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area26
Heavy Atom Count9
Formal Charge0
Complexity97.1
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 four (14)C-labeled thiobis(formamidine) insecticides was studied in Sprague Dawley rats & ICR mice. The insecticides were derived from a series of 2,4-disubstituted anilines. The compounds studied included 2,4-dichloroaniline. Each compound was orally admin in corn oil solution to 2 female rats & 4 female mice in doses of 10-13 mg/kg. In every case, the corresponding anilines were detected as free aniline, in minor amounts except for the dichloro series. There were no significant differences observed between the compounds studied. The general metabolism schemes for all 4 compounds were similar. Metabolism of these compounds involves rapid hydrolysis of the parent compound in the stomach to simple formamidine, which is then converted to an N-formylaniline that has various metabolic fates, particularly through oxidation of methyl groups.

Hornish RE; J Agri Food Chem 32 (1): 114-9 (1984)


In order to reveal the urinary metabolites of p-chloronitrobenzene (CNB), an investigation was conducted to separate and identify urinary metabolites by gas chromatography/mass spectrometry following the administration of the compound to rats. Six male Sprague-Dawley-rats were given a single dose of 100 mg/kg CNB diluted in olive-oil and injected intraperitoneally. Urine was collected from the six rats at from 8 to 24 hours after exposure. Trace amounts of unchanged CNB were detected in the urine of the rats, but most of the CNB appeared to have been metabolized prior to excretion. Nine substances were identified: p-chloroaniline, 2,4-dichloroaniline, p-nitrothiophenol, 2-chloro-5-nitrophenol, 2-amino-5-chlorophenol, p-chloroformanilide, 4-chloro-2-hydroxyacetanilide, a small amount of p-chloroacetanilide and traces of unchanged CNB.

Yoshida T et al; Archives of Toxicol 65 (1): 52-8 (1991)


The urinary metabolites of p-chloronitrobenzene (p-CNB) in humans were determined using urine samples from acutely poisoned subjects. The six subjects were longshoremen hospitalized after being exposed to p-CNB while loading torn bags of the substance. Moment analysis and compartment model analysis of the urinary excretion rate of metabolites of p-CNB versus time curves were used for the pharmacokinetic evaluation. The findings suggest that the average values of the ratio of excreted amount of each metabolite to the total amount of the five metabolites and mean residence time in the six subjects were, respectively, 12.2% and 6.7 days for 2-chloro-5-nitrophenol (619103), 48.0% and 7.0 days for N-acetyl-S-(4-nitrophenyl)-L-cysteine, 1.2% and 3.7 days for 2,4-dichloroaniline, 29.9% and 10.0 days for p-chloroaniline, and 8.7% and 6.0 days for 2-amino-5-chlorophenol. The rates of transformation of p-CNB to 2-chloro-5-nitrophenol and p-chloroaniline appeared to be slow, but the resulting p-chloroaniline was metabolized relatively rapidly in the human body. The authors note that the ratio of the excretion amounts of the five metabolites was nearly constant among the subjects, whereas the rate of metabolism of the parent compound and the mean residence time varied widely among the individuals.

PMID:7905396 Yoshida T et al; Drug Metabolism and Disposition 21 (6): 1142-6 (1993)


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