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Overview of 371-40-4

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

1 2D Structure

4flouroaniline

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. 1-amino-4-fluorobenzene

4. Benzenamine, 4-fluoro-

5. 4-fluorobenzenamine

6. P-fluorophenylamine

7. 4-fluoronaniline

8. Aniline, P-fluoro-

9. Aniline, 4-fluoro-

10. 4-fluoranilin

11. Para-fluoroaniline

12. 4-fluoro-phenylamine

13. 4-fluorophenylamine

14. 4-fluoranilin [czech]

15. Nsc 579

16. Mfcd00007829

17. P-aminofluorobenzene

18. Para-fluoro Aniline

19. Unii-60hi1g076z

20. 4-fluoro-benzenamine

21. Ccris 5059

22. Hsdb 2691

23. (4-fluorophenyl)-amine

24. Einecs 206-735-5

25. Brn 0742030

26. Ai3-52386

27. Chebi:28546

28. Krzcolnoczksdf-uhfffaoysa-n

29. 60hi1g076z

30. 4-fluoranylaniline

31. 4-fluoroaniline, 98%

32. 4-fluoroaniline Hcl

33. 4flouroaniline

34. 4-flouroaniline

35. 4-floroaniline

36. 4-fluoroanilin

37. 4-fluroaniline

38. P-fluoro-aniline

39. 4 -fluoroaniline

40. 4- Fluoroaniline

41. 4-fluoro Aniline

42. 4-fluoro-aniline

43. 4-fluorobenzeneamine

44. 4-fluorobenzenaminium

45. (4-fluorophenyl)amine

46. Pubchem10782

47. 4-fluoro-1-aminobenzene

48. 4-fluoroaniline, 99%

49. Ac1l1toy

50. Acmc-1cqn1

51. Dsstox_cid_2027

52. Wln: Zr Df

53. Ec 206-735-5

54. Schembl3199

55. Dsstox_rid_76464

56. Dsstox_gsid_22027

57. Aniline, P-fluoro- (8ci)

58. 4-12-00-01104 (beilstein Handbook Reference)

59. Ksc223i0p

60. Chembl32014

61. Ac1q521g

62. Nsc579

63. Dtxsid9022027

64. Ctk1c3407

65. Timtec-bb Sbb040453

66. Zinc13613

67. Nsc-579

68. Otava-bb 1506428

69. Akos 91149

70. Labotest-bb Ltbb000713

71. Act00169

72. Bcp21217

73. Ks-000002my

74. Akos Bbs-00003571

75. Tox21_202828

76. Anw-28573

77. Sbb040453

78. Stl168895

79. Akos000119114

80. Am61493

81. An-1239

82. As01509

83. Hf10028

84. Mcule-2548375851

85. Ps-9263

86. Rp19010

87. Rtc-050925

88. Tra0043880

89. Un 2944

90. Ncgc00260374-01

91. Aj-08366

92. Bc226190

93. Cas-371-40-4

94. Cj-00133

95. Ls-19821

96. Sc-18651

97. Zb000715

98. Db-023950

99. St2411430

100. Tc-050925

101. Tl8002733

102. F0033

103. Ft-0618502

104. St45255294

105. 4-fluoroaniline, Technical, >=97.0% (gc)

106. Az0001-0088

107. C11014

108. M-6082

109. 24366-ep2275413a1

110. 24366-ep2280001a1

111. 24366-ep2281563a1

112. 24366-ep2284157a1

113. 24366-ep2287156a1

114. 24366-ep2305660a1

115. 24366-ep2305695a2

116. 24366-ep2305696a2

117. 24366-ep2305697a2

118. 24366-ep2305698a2

119. 24366-ep2314590a1

120. A823539

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

122. I01-0507

123. J-515394

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

125. Z57127563

126. F2190-0427

127. Inchi=1/c6h6fn/c7-5-1-3-6(8)4-2-5/h1-4h,8h

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 Mass111.048427 g/mol
Monoisotopic Mass111.048427 g/mol
Topological Polar Surface Area26 A^2
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.

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


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.

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


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)


The urinary metabolic fate of 4-fluoroaniline (4-FA) and 1-[13C]-4-fluoroacetanilide (4-FAA) has been studied using NMR-based methods after 50 and 100 mg kg(-1) ip doses respectively to the male Sprague-Dawley rat. 2. 4-FA was both ortho- and para-hydroxylated. The major metabolite produced by ortho-hydroxylation was 2-amino-5-fluorophenylsulphate accounting for approximately 30% of the dose. Of the dose, approximately 10% was excreted via para-hydroxylation and the resulting defluorinated metabolites were N-acetylated and excreted as sulphate (major), glucuronide (minor) and N-acetyl-cysteinyl (minor) conjugates of 4-acetamidophenol (paracetamol). 3. The major route of metabolism of 1-(13)C-4-FAA was N-deacetylation and the metabolites excreted in the urine were qualitatively identical to 4-FA. The paracetamol metabolites produced via para-hydroxylation were also a product of N-deacetylation and reacetylation, as the (13)C-label was not retained. 4. These studies demonstrate the value of (13)C-labelling in understanding the contribution of N-acetylation, and futile deacetylation-reacetylation reactions, in aniline metabolism. In addition, this work sheds new light on the metabolic lability of certain aromatic fluorine substituents.

Scarfe GB et al; Xenobiotica 29 (2): 205-16 (1999) PMID:10199596


Possible methods for monitoring exposure to 2,4-difluoroaniline and 4-fluoroaniline were studied in rats. Wistar-rats were given 1.0, 0.5, 0.25, and 0.13 millimoles per 0.1 kilogram 2,4-difluoroaniline or 4-fluoroaniline or 1.0 millimole per kilogram 4-chloroaniline as a positive control. Blood samples were taken at 1 hour before and 1, 2, 4, 6, 8, and 24 hours after dosing. Methemoglobin was calculated from absorbance at 630 nanometers before and after adding potassium-cyanide to lysed blood. Urinary metabolites were isolated as cetylpyridinium salts from rats similarly dosed with 4-fluoroaniline and 2,4-difluoroaniline. Metabolites were identified by nuclear magnetic resonance and elemental analysis. Neither test compound was as potent an inducer of methemoglobin as the positive control. At all doses of either compound methemoglobin increased rapidly and dropped quickly, returning to background values by 24 hours except at the highest doses. The dose response for each compound was approximately linear. The limit of detection was about 5 milligrams per 0.1 kilogram. 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 compounds was rapid and only low concentrations were detected the second day after dosing. About 39 percent of 4-fluoroaniline and 13 percent of 2,4-difluoroaniline were accounted for by these metabolites. The authors conclude that either method could be used for human exposure monitoring. Methemoglobin determination is rapid and simple but not a very sensitive indicator. Urinary metabolite measurement is more sensitive but more complicated to perform.

Eadsforth CV et al; Intl Archives of Occupational and Environmental Health 54 (3): 223-32 (1984)


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