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Also known as: 106-46-7, P-dichlorobenzene, Paradichlorobenzene, Para-dichlorobenzene, Paracide, Paramoth

Molecular Formula

C₆H₄Cl₂

Molecular Weight

147.00 g/mol

InChI Key

OCJBOOLMMGQPQU-UHFFFAOYSA-N

FDA UNII

D149TYB5MK

Paradichlorobenzene is a synthetic, white crystalline solid that is practically insoluble in water and soluble in ether, chloroform, carbon disulfide, benzene, alcohol and acetone. It is used primarily as a space deodorant in products such as room deodorizers, urinal and toilet bowl blocks, and as an insecticide fumigant for moth control. When 1,4-dichlorobenzene is heated to decomposition, toxic gases and vapors (such as hydrochloric acid and carbon monoxide) are released. The primary route of potential human exposure to this compound is inhalation. Acute inhalation exposure to 1,4-dichlorobenzene can result in coughing and breathing difficulties. Breathing high levels of this chemical can cause headaches, dizziness and liver damage. Contact with 1,4-dichlorobenzene can irritate the eyes, leading to burning and tearing. It is reasonably anticipated to be a human carcinogen. (NCI05)

1 2D Structure

Dichlorobenzene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,4-dichlorobenzene

2.1.2 InChI

InChI=1S/C6H4Cl2/c7-5-1-2-6(8)4-3-5/h1-4H

2.1.3 InChI Key

OCJBOOLMMGQPQU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

D149TYB5MK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-dichlorobenzene

2. P-dichlorobenzene

3. Para-dichlorobenzene

4. Paradichlorobenzene

2.3.2 Depositor-Supplied Synonyms

1. 106-46-7

2. P-dichlorobenzene

3. Paradichlorobenzene

4. Para-dichlorobenzene

5. Paracide

6. Paramoth

7. Benzene, 1,4-dichloro-

8. Dichlorobenzene

9. Paranuggets

10. Santochlor

11. Paradow

12. Evola

13. P-dichlorbenzol

14. Persia-perazol

15. P-dichlorobenzol

16. P-chlorophenyl Chloride

17. Globol

18. Para Crystals

19. Dichlorocide

20. Paradi

21. Di-chloricide

22. Paradichlorbenzol

23. Para

24. Pdcb

25. P-diclorobenzene

26. 1,4-dichloorbenzeen

27. P-dichloorbenzeen

28. Paradichlorobenzol

29. 1,4-dichlor-benzol

30. Dichloricide

31. 1,4-diclorobenzene

32. Benzene, P-dichloro-

33. 1,4-dichloro-benzene

34. Parazene

35. Rcra Waste Number U070

36. Rcra Waste Number U071

37. Rcra Waste Number U072

38. Para-zene

39. Dichlorobenzene, P-

40. Nci-c54955

41. Kaydox

42. P-dichlorbenzene

43. Pdb

44. Nsc 36935

45. Dichlorobenzene, Para

46. D149tyb5mk

47. Chembl190982

48. Chebi:28618

49. Nsc-36935

50. Ncgc00094540-01

51. 1,3-cyclohexadien-5-yne,1,4-dichloro-

52. Dsstox_cid_431

53. 106-46-725321-22-6(mixedisomers)

54. 4-dichlorobenzene

55. Dsstox_rid_75582

56. Dsstox_gsid_20431

57. 1,4 Dichlorobenzene

58. P-dcb

59. Caswell No. 632

60. P-dichlorbenzol [german]

61. P-dichloorbenzeen [dutch]

62. Paradichlorbenzol [german]

63. P-diclorobenzene [italian]

64. 1,4-chlorobenzene

65. Cas-106-46-7

66. Ccris 307

67. 1,4-dichloorbenzeen [dutch]

68. 1,4-dichlor-benzol [german]

69. 1,4-diclorobenzene [italian]

70. Hsdb 523

71. Einecs 203-400-5

72. Rcra Waste No. D027

73. Rcra Waste No. U072

74. Unii-d149tyb5mk

75. Epa Pesticide Chemical Code 061501

76. Diclorobenzene

77. Ai3-0050

78. P-dichlorobenzen

79. Ai3-00050

80. P-dichloro-benzene

81. Mfcd00000604

82. Benzene,4-dichloro-

83. Dichlorobenzene, Solid

84. 1, 4-dichlorobenzene

85. Spectrum_001891

86. Specplus_000512

87. Benzene, 1,4-dichloro-, Radical Ion(1-)

88. Spectrum2_001869

89. Spectrum3_000846

90. Spectrum4_000686

91. Spectrum5_002008

92. P-dichlorbenzol(german)

93. P-dichloorbenzeen(dutch)

94. Para-dichlorobenzene,(s)

95. Wln: Gr Dg

96. Ec 203-400-5

97. P-diclorobenzene(italian)

98. Dichlorobenzene, P-, Solid

99. Schembl5191

100. Bspbio_002431

101. Kbiogr_001151

102. Kbioss_002421

103. Spectrum330055

104. Bidd:er0278

105. Divk1c_006608

106. Spbio_001718

107. P-dichlorobenzene [mi]

108. 1, 4-dichloorbenzeen(dutch)

109. 1,4-dichlor-benzol(german)

110. 1,4-diclorobenzene(italian)

111. Dtxsid1020431

112. 1,4-dichlorobenzene, >=99%

113. Kbio1_001552

114. Kbio2_002415

115. Kbio2_004983

116. Kbio2_007551

117. Kbio3_001931

118. Paradichlorobenzene [vandf]

119. Zinc388507

120. Paradichlorobenzene [mart.]

121. Amy40774

122. Hy-y0496

123. Nsc36935

124. 1,4-dichlorobenzene [hsdb]

125. Paradichlorobenzene [who-dd]

126. Tox21_111293

127. Tox21_200399

128. Tox21_300018

129. 1,4-dichlorobenzene-ul-14c, Neat

130. Bdbm50159263

131. C0593

132. Ccg-39407

133. S6300

134. Stl445582

135. Akos000120016

136. Un 1592

137. 1,4-dichlorobenzene (acd/name 4.0)

138. Ncgc00094540-02

139. Ncgc00094540-03

140. Ncgc00094540-04

141. Ncgc00094540-05

142. Ncgc00253934-01

143. Ncgc00257953-01

144. 55232-43-4

145. Benzene,1-chloro-4-(chloro-38cl)-(9ci)

146. Cs-0015284

147. D0687

148. Ft-0606862

149. S0666

150. 1,4-dichlorobenzene 10 Microg/ml In Isooctane

151. C07092

152. 1,4-dichlorobenzene 100 Microg/ml In Methanol

153. 1,4-dichlorobenzene 1000 Microg/ml In Methanol

154. 1,4-dichlorobenzene, Saj First Grade, >=99.0%

155. Q161529

156. J-503986

157. 1,4-dichlorobenzene, Pestanal(r), Analytical Standard

158. F0001-0123

159. Hexanedioic Acid, Polymer With 1,3-butanediol, Diesters With C14-18 Fatty Acids

160. 68890-93-7

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₆H₄Cl₂
Molecular Weight	147.00 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	0
Exact Mass	145.9690055 g/mol
Monoisotopic Mass	145.9690055 g/mol
Topological Polar Surface Area	0 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	54.9
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Carcinogens

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)

4.2 Absorption, Distribution and Excretion

The material is apparently well absorbed by the gastrointestinal tract and from lung but not appreciably through skin.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 3625

Moth repellent para-dichlorobenzene was detected in human adipose tissue and blood as pollutant together with polychlorinated biphenyls.

Kimura R et al; J Pharmacobio-dyn 2 (4): 237-44 (1980)

Absorption of 1,4-dichlorobenzene through the gastrointestinal tract is rapid. Oral doses of 200 or 800 mg/kg to male Wistar rats appeared in the blood and adipose, kidney, liver, lung, heart, and brain tissue within 30 minutes.

Kimura R et al; J Pharm Dyn 2 (4): 237-44 (1980) as cited in USEPA; Health Assessment Document: Chlorinated Benzenes p.8-2 (1985) EPA-600/8-84-015

The dichlorobenzenes may be absorbed through the lungs, gastrointestinal tract, and the intact skin. Relatively low water solubility and high lipid solubility favor their penetration of most membranes by diffusion, including pulmonary and GI epithelia, the brain, hepatic parenchyma, renal tubules, and the placenta. /Dichlorobenzenes/

Ware S, West WL; Investigation of Selected Potential Environmental Contaminants: Halogenated Benzenes (1977) EPA 560/2-77-004 as cited in USEPA; Ambient Water Quality Criteria Doc: Dichlorobenzenes p.C-11 (1980) EPA 400/5-80-039

For more Absorption, Distribution and Excretion (Complete) data for 1,4-Dichlorobenzene (14 total), please visit the HSDB record page.

4.3 Metabolism/Metabolites

A novel in vitro system was used to evaluate tissue specific toxicity. This system utilizes precision cut organ slices in dynamic organ culture and is viable for up to 24 hrs. The three isomers of dichlorobenzene were added to liver slices prepared from Sprague Dawley rats or human donors. The precursor dichlorobenzenes were radiolabelled and metabolites were separated by classes (i.e. glucuronides, sulfates and glutathione and cysteine conjugates). Covalent Binding of the dichlorobenzenes was also determined after extensive extraction of the tissue. The total amount of metabolism of the dichlorobenzenes varied depending on the isomer and the type of tissue. For example, the Sprague-Dawley rat liver slices metabolized 1,2-DCB and 1,3-DCB at approximately the same rate while 1,4-DCB was metabolized at a slower rate. This metabolism profile was also seen in the majority of the adult human liver slices. However, the fetal human slices showed that 1,4-DCB was metabolized to a greater extent than 1,3-DCB or 1,2-DCB while 1,3-DCB was metabolized at a faster rate than 1,2-DCB. Our results show that liver slices in organ culture are a suitable system for species comparisons and of structure/activity relationships in xenobiotic metabolism with an emphasis on the fate of reactive intermediates. In addition, this system is suitable for evaluation of hepatotoxic potency.

PMID:2069046 Fisher R et al; Adv Exp Med Biol 283: 717-23 (1991)

After ingestion of p-dichlorobenzene, 2,5-dichlorophenol (30%) free and as the glucuronide and sulfate and 2,5-dichloroquinol (6%) were excreted. In humans, 2,5-dichlorophenol was also found in the urine.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 155

After oral administration of para-dichlorobenzene to rats, 2 metabolites detected in blood. Metabolites M-1 and M-2 are 2,5-dichlorophenyl methyl sulfoxide and 2,5-dichlorophenyl methyl sulfone. Concentration of M-1 in blood was higher than M-2 for 12 hr after dosing, but blood level of M-2 was higher thereafter. After oral administration of p-DCB to rats 2,5-dichlorophenol was major metabolite.

Kimura R et al; J Pharmacobio-dyn 2 (4): 237-44 (1980)

Rabbits were fed an oral dose of 0.5 g/kg of p-dichlorobenzene /which was then/ oxidized to 2,5-dichlorophenol (35%); conjugated to form glucuronide (36%) and ethereal sulfate (27%); or excreted as 2,5-dichloroquinol (6%).

Azouz WM et al; Biochem Jour 59: 410-5 (1955)

For more Metabolism/Metabolites (Complete) data for 1,4-Dichlorobenzene (9 total), please visit the HSDB record page.

1,4-dichlorobenzene has known human metabolites that include 2,5-dichlorophenol.

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

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