Close
4

Athena Athena

X

CAS 371-40-4 manufacturers and suppliers on PharmaCompass

PharmaCompass
371-40-4
Also known as: 371-40-4, P-fluoroaniline, 4-fluorobenzenamine, 1-amino-4-fluorobenzene, Benzenamine, 4-fluoro-, P-fluorophenylamine
Molecular Formula
C6H6FN
Molecular Weight
111.12  g/mol
InChI Key
KRZCOLNOCZKSDF-UHFFFAOYSA-N
FDA UNII
60HI1G076Z

1 2D Structure

371-40-4

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-fluoroaniline
2.1.2 InChI
InChI=1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
2.1.3 InChI Key
KRZCOLNOCZKSDF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1N)F
2.2 Other Identifiers
2.2.1 UNII
60HI1G076Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-fluoroaniline Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 371-40-4

2. P-fluoroaniline

3. 4-fluorobenzenamine

4. 1-amino-4-fluorobenzene

5. Benzenamine, 4-fluoro-

6. P-fluorophenylamine

7. 4-fluoronaniline

8. Para-fluoroaniline

9. Aniline, P-fluoro-

10. 4-fluoro-phenylamine

11. Aniline, 4-fluoro-

12. 4-fluoranilin

13. 4-fluorophenylamine

14. Nsc 579

15. Mfcd00007829

16. P-aminofluorobenzene

17. 4-fluorobenzenaminium

18. Chebi:28546

19. (4-fluorophenyl)-amine

20. Chembl32014

21. Dtxsid9022027

22. Nsc-579

23. 60hi1g076z

24. 4-fluoranilin [czech]

25. Fluoroaniline, P-

26. Ccris 5059

27. Hsdb 2691

28. Einecs 206-735-5

29. Brn 0742030

30. 4flouroaniline

31. P-fluoraniline

32. Unii-60hi1g076z

33. 4-flouroaniline

34. 4-floroaniline

35. 4-fluoroanilin

36. 4-fluroaniline

37. Ai3-52386

38. P-fluoro-aniline

39. 4 -fluoroaniline

40. 4- Fluoroaniline

41. 4-fluoro Aniline

42. 4-fluoro-aniline

43. 4-fluoranylaniline

44. 4-fluorobenzeneamine

45. (4-fluorophenyl)amine

46. 1,4-fluorobenzenamine

47. 4-fluoro-1-aminobenzene

48. 4-fluoroaniline, 99%

49. Dsstox_cid_2027

50. Wln: Zr Df

51. Ec 206-735-5

52. Schembl3199

53. Dsstox_rid_76464

54. Dsstox_gsid_22027

55. 4-12-00-01104 (beilstein Handbook Reference)

56. 4-fluoroaniline [mi]

57. Nsc579

58. 4-fluoroaniline [hsdb]

59. Zinc13613

60. Act00169

61. Bcp21217

62. Tox21_202828

63. Bdbm50282614

64. Stl168895

65. Akos000119114

66. Am61493

67. Ps-9263

68. Un 2944

69. Ncgc00260374-01

70. Cas-371-40-4

71. Db-023950

72. F0033

73. Ft-0618502

74. 4-fluoroaniline, Technical, >=97.0% (gc)

75. D78529

76. A823539

77. J-515394

78. P-fluoroaniline [un2941] [keep Away From Food]

79. Q27103764

80. Z57127563

81. F2190-0427

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 111.12 g/mol
Molecular Formula C6H6FN
XLogP31.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass111.048427358 g/mol
Monoisotopic Mass111.048427358 g/mol
Topological Polar Surface Area26 Ų
Heavy Atom Count8
Formal Charge0
Complexity66.9
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 in vitro hydroxylation-defluorination of p-fluoroaniline was carried out by liver microsomes from the rabbit, rat, sheep, cow, pig, man and pigeon, but not by microsomes prepared from trout.

PMID:5646022 Renson J, Bourdon V; Arch Int Pharmacodyn Ther 171 (1): 240 (1968)


p-Fluoroaniline is defluorinated notably in vivo in rats, clearly evidenced by the increase in urinary fluoride.

Truhaut R et al; J Eur Toxicol 5 (3): 155 (1972)


Possible methods for monitoring exposure to 2,4-difluoroaniline and 4-fluoroaniline were studied in rats. Wistar rats were given 1.0, 0.25, and 0.13 millimoles per 0.1 kilogram 2,4-difluoroaniline or 4-fluoroaniline. Blood samples were taken at 1 hr before and 1, 2, 4, 6, 8, and 24 hr after dosing. Methemoglobin was calculated from absorbance at 630 nm before and after adding potassium cyanide to lysed blood. Urinary metabolites were isolated as cetylpyridinium salts from rats similarily dosed with 4-fluoroaniline and 2,4,-difluoroaniline. Analysis of urinary metabolites confirmed that these were the o-sulfates of 2-amino-5-aminophenol and 2-amino-3,5-difluorophenol. The excretion of the urinary conjugated aminophenols after oral dosing with these cmpd was rapid and only low concentrations were detected the second day after dosing. About 39% of 4-fluoroanilne and 13% of 2,4-difluoroaniline were accounted by these metabolites.

PMID:6490181 Eadsforth CV et al; Int Arch Occup Environ Health 54 (3): 223-32 (1984)


The regioselectivity and metabolism of monofluoroanilines were studied in-vivo and in-vitro. Male Wistar-rats were administered 0 or 50 mg/kg 2-fluoroaniline, 3-fluoroaniline, or 4-fluoroaniline orally. Urine samples were collected 24 hours later and analyzed for metabolites by fluorine-19 nuclear magnetic resonance spectroscopy. Liver microsomes prepared from male Wistar-rats that had been pretreated with the cytochrome-P-450 (P450) inducers were fortified with P450 and incubated with 0 or 10 millimolar 2-fluoroaniline, 3-fluoroaniline, or 4-fluoroaniline for 10 minutes. The incubates were analyzed for metabolites. Frontier electron densities of occupied and unoccupied orbitals of 2-fluoroaniline, 3-fluoroaniline, and 4-fluoroaniline were calculated by a computerized semiempirical molecular orbital technique. 3-Fluoro-4-acetamidophenylsulfate, 3-fluoro-4-aminophenylsulfate, and 3-fluoro-4-acetamidophenylglucuronide were the major 2-fluoroaniline urinary metabolites. 2-Fluoro-4-acetamidophenylsulfate, 4-fluoro-2-aminophenylsulfate, 2-fluoro-4-aminophenylsulfate, and the fluoride-ion (F-) were the major metabolites of 3-fluoroaniline. 5-Fluoro-2-aminophenylsulfate and fluoride-ion were the major metabolites of 4-fluoroaniline. In-vitro, 3-fluoro-4-aminophenol was the major 2-fluoroaniline metabolite. 3-Fluoroaniline was converted primarily to 4-aminophenol and 4-fluoro-2-aminophenol. 4-Fluoroaniline was converted primarily to 5-fluoro-2-aminophenol and F-. In microsomes from rats pretreated with the P450 inducers, 3-fluoroaniline underwent hydroxylation primarily in the para position, the extent of hydroxylation being similar for all pretreatment conditions. Ortho hydroxylation at the C6 position occurred under all pretreatment conditions but to a much smaller extent. Ortho hydroxylation at the C2 position occurred only in microsomes from rats pretreated with 3MC and isosafrole. Frontier electron densities in the highest occupied molecular orbital (HOMO) and the orbital just below it (HOMO-1) were highest in the C4 position followed by the C6 and C2 positions. /The investigators/ conclude that the regioselectivity in the hydroxylation of 3-fluoroaniline can be explained by higher electron densities in the HOMO and HOMO-1 orbitals of the C4 and C6 carbons and the low density at the C2 position. P450 catalyzed hydroxylation of monofluoroanilines apparently involves electrophilic attack of a charged iron/oxygen species derived from P450 on a specific carbon atom of the aromatic ring.

Cnubben NHP et al; Chemico-Biological Interactions 85 (2/3): 151-172 (1992)


For more Metabolism/Metabolites (Complete) data for 4-FLUOROANILINE (6 total), please visit the HSDB record page.


Ask Us for Pharmaceutical Supplier and Partner
Ask Us, Find A Supplier / Partner
No Commissions, No Strings Attached, Get Connected for FREE

What are you looking for?

How can we help you?

The request can't be empty

Please read our Privacy Policy carefully

You must agree to the privacy policy

The name can't be empty
The company can't be empty.
The email can't be empty Please enter a valid email.
The mobile can't be empty
Post Enquiry
POST ENQUIRY