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Also known as: 106-48-9, P-chlorophenol, Parachlorophenol, Phenol, 4-chloro-, 4-hydroxychlorobenzene, Phenol, p-chloro-

Molecular Formula

C₆H₅ClO

Molecular Weight

128.55 g/mol

InChI Key

WXNZTHHGJRFXKQ-UHFFFAOYSA-N

FDA UNII

3DLC36A01X

P-chlorophenol is a white crystals with a strong phenol odor. Slightly soluble to soluble in water, depending on the isomer, and denser than water. Noncombustible.

1 2D Structure

4-Chlorophenol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-chlorophenol

2.1.2 InChI

InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H

2.1.3 InChI Key

WXNZTHHGJRFXKQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1O)Cl

2.2 Other Identifiers

2.2.1 UNII

3DLC36A01X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-chlorophenol Ion (1+)

2. 4-chlorophenol, Copper (+1) Salt

3. 4-chlorophenol, Nickel (+2) Salt

4. 4-chlorophenol, Potassium Salt

5. 4-chlorophenol, Sodium Salt

6. 4-chlorophenol, Titanium (+4) Salt

7. 4-chlorophenoxide

8. 4-monochlorophenol

9. P-chlorophenol

10. Para-monochlorophenol

11. Parachlorophenol

2.3.2 Depositor-Supplied Synonyms

1. 106-48-9

2. P-chlorophenol

3. Parachlorophenol

4. Phenol, 4-chloro-

5. 4-hydroxychlorobenzene

6. Phenol, P-chloro-

7. Applied 3-78

8. 4-monochlorophenol

9. P-chlorophenic Acid

10. P-chlorfenol

11. 4-chlorphenol

12. 4-chloro-1-hydroxybenzene

13. P-chlorfenol [czech]

14. 4-chloro-phenol

15. Nsc 2877

16. Mfcd00002318

17. Parachlorophenol (jan/usp)

18. 3dlc36a01x

19. Chebi:28078

20. Nsc-2877

21. Ncgc00090814-01

22. Dsstox_cid_1871

23. Dsstox_rid_76376

24. Dsstox_gsid_21871

25. P-chlorophenol, Liquid [un2021] [keep Away From Food]

26. P-chlorophenol, Solid [un2020] [keep Away From Food]

27. Parachlorophenol [usp]

28. Cas-106-48-9

29. Ccris 642

30. Hsdb 1414

31. Einecs 203-402-6

32. Unii-3dlc36a01x

33. 4chlorophenol

34. P-chloro Phenol

35. Ai3-19422

36. Para-chlorophenol

37. Parachloro Phenol

38. 4-chloro Phenol

39. 4ch

40. Parachlorophenol,(s)

41. P-chlorophenol, Solid

42. P-chlorophenol, Liquid

43. Spectrum_000939

44. Spectrum2_000968

45. Spectrum3_000539

46. Spectrum4_000468

47. Spectrum5_001228

48. Wln: Qr Dg

49. 4-clc6h4oh

50. Bmse000461

51. Ec 203-402-6

52. 4-chlorophenol, >=99%

53. P-chlorophenol [mi]

54. Schembl28864

55. Bspbio_002157

56. Kbiogr_000916

57. Kbioss_001419

58. Mls002454432

59. Bidd:er0011

60. Chembl57053

61. Divk1c_000310

62. P-chlorophenol [inci]

63. Parachlorophenol [jan]

64. Spectrum1500460

65. Spbio_000975

66. Parachlorophenol [hsdb]

67. Zinc1885

68. Parachlorophenol [vandf]

69. 4-chlorphenol [who-dd]

70. Dtxsid1021871

71. Parachlorophenol [mart.]

72. Bdbm36299

73. Hms500p12

74. Kbio1_000310

75. Kbio2_001419

76. Kbio2_003987

77. Kbio2_006555

78. Kbio3_001657

79. Nsc2877

80. Parachlorophenol [usp-rs]

81. Ninds_000310

82. Hms1920f08

83. Hms2091n08

84. Hms2230b13

85. Hms3373o02

86. Pharmakon1600-01500460

87. Tox21_111028

88. Tox21_201704

89. Tox21_302860

90. Ccg-40184

91. Nsc757263

92. Stl194293

93. 4-chlorophenol, For Synthesis, 98%

94. Akos000118967

95. Tox21_111028_1

96. Db13154

97. Nsc-757263

98. Idi1_000310

99. Parachlorophenol [usp Monograph]

100. Ncgc00090814-02

101. Ncgc00090814-03

102. Ncgc00090814-04

103. Ncgc00090814-05

104. Ncgc00090814-07

105. Ncgc00256497-01

106. Ncgc00259253-01

107. 4-chlorophenol 10 Microg/ml In Methanol

108. Smr001252242

109. 4-chlorophenol 100 Microg/ml In Methanol

110. Sbi-0051474.p003

111. Db-028832

112. 4-chlorophenol, Puriss., >=99.0% (gc)

113. Cs-0005709

114. Ft-0618238

115. 4-chlorophenol 100 Microg/ml In Isopropanol

116. 4-chlorophenol 1000 Microg/ml In Isopropanol

117. C02124

118. D00149

119. Ab00052066_06

120. 4-chlorophenol, Pestanal(r), Analytical Standard

121. Sr-05000001691

122. J-001599

123. Q2179668

124. Sr-05000001691-1

125. Brd-k40992116-001-05-5

126. F0001-0124

127. Z1262246118

128. Parachlorophenol, United States Pharmacopeia (usp) Reference Standard

129. 4-chlorophenol Solution, 725 Mg/l In H2o, For Aox Determination (according To Din 38409-h14)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₅ClO
Molecular Weight	128.55 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	128.0028925 g/mol
Monoisotopic Mass	128.0028925 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	66.9
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Local antibacterial agent in root canal therapy

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1111

Topical antiseptic /cat/

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 359

Medication (Vet): /Formerly/ as topical antiseptic in ointments

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 106

4.2 Drug Indication

Used as an intermediate in organic synthesis of dyes and drugs. Local antibacterial agent in root canal therapy, as topical antiseptic in ointments

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

5.2 Absorption, Distribution and Excretion

Absorption

absorbed from gastrointestinal tract.

Route of Elimination

87% of 4-chlorophenol was excreted in urine of dogs as sulfate and glucuronide.

A number of rabbit studies have shown that metabolism of the monochlorophenols is principally via conjugation. In one study, groups of 6 rabbits were treated by gavage with 171.3 mg/kg of 2-CP or 4-CP emulsified in water as a single dose. For both isomers, the 24-hour urine analysis indicated that between 78.1 and 88.3% of the administered dose was excreted as the glucuronide, and between 12.8 and 20.6% of the administered dose was excreted as the ethereal sulfate. A total of 101.7 and 101.1% of the administered 2-CP or 4-CP doses, respectively, was accounted for as urinary glucuronide and sulfate conjugates.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Chlorophenols PB/99/166639 p.80 (July 1999). Available from, as of October 28, 2008: https://www.atsdr.cdc.gov/toxpro2.html#

Metabolism was ... investigated in 4 rabbits, each treated by gavage with an average dose of 395 mg/kg/day of 4-CP. After 36 hours, 54.1% of the administered dose appeared in the urine as the glucuronide conjugate, and 10.4% of the administered dose appeared in the ethereal sulfate fraction. Only 0.1% of the administered dose was excreted as 4-chlorocatechol. The low total recovery (64.5%) in the latter experiment limits conclusions.

In a limited study in dogs about half of an oral dose of 2- or 4-CP was excreted in the urine as the ethereal sulfate. No evidence for metabolism to mercapturic acid was found.

... Absorbed from ... gastrointestinal tract & ... parenteral sites of injection. ... Excreted as conjugates of sulfuric & glucuronic acid. ... Urine darkens after standing /Chlorophenols/

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 1615-16

5.3 Metabolism/Metabolites

P-Chlorophenol yields p-chloroanisole in guinea pigs. P-Chlorophenol yields 4-chlorocatechol p-chloro phenyl-beta-D-glucuronide & p-chlorphenyl sulfate in rabbits. P-Chlorophenol yields p-chlorophenyl sulfate in rats.

P-Chlorophenol yields p-chloroanisole in guinea pigs.

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-36

P-Chlorophenol yields 4-chlorocatechol p-chloro phenyl-beta-D-glucuronide & p-chlorphenyl sulfate in rabbits.

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-36

P-Chlorophenol yields p-chlorophenyl-beta-D-glucuronide * p-chlorophenyl sulfate in hens.

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-36

P-Chlorophenol yields p-chlorophenyl sulfate in rats.

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-36

For more Metabolism/Metabolites (Complete) data for 4-CHLOROPHENOL (10 total), please visit the HSDB record page.

4-Chlorophenol has known human metabolites that include (2S,3S,4S,5R)-6-(4-Chlorophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.4 Mechanism of Action

The major mode of action of chlorophenols appears to be the uncoupling of oxidative phosphorylation. The strength of the uncoupling effect is related to the degree of chlorination: PCP is the strongest inhibitor of oxidative phosphorylation, MCP the weakest. To a lesser extent, inhibition of oxidative phosphorylation is affected by the positions of the chlorine atoms on the molecule.

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