Please Wait
Applying Filters...
Menu
$ API Ref.Price (USD/KG) : 1Xls
2D Structure
Also known as: Benzol, 71-43-2, Cyclohexatriene, Benzole, Pyrobenzole, Benzine
Molecular Formula
C6H6
Molecular Weight
78.11  g/mol
InChI Key
UHOVQNZJYSORNB-UHFFFAOYSA-N
FDA UNII
J64922108F

Toxic, volatile, flammable liquid hydrocarbon byproduct of coal distillation. It is used as an industrial solvent in paints, varnishes, lacquer thinners, gasoline, etc. Benzene causes central nervous system damage acutely and bone marrow damage chronically and is carcinogenic. It was formerly used as parasiticide.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
benzene
2.1.2 InChI
InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
2.1.3 InChI Key
UHOVQNZJYSORNB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=CC=C1
2.2 Other Identifiers
2.2.1 UNII
J64922108F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Benzol

2. Benzole

3. Cyclohexatriene

2.3.2 Depositor-Supplied Synonyms

1. Benzol

2. 71-43-2

3. Cyclohexatriene

4. Benzole

5. Pyrobenzole

6. Benzine

7. Benzen

8. Phenyl Hydride

9. Coal Naphtha

10. Pyrobenzol

11. Phene

12. Mineral Naphtha

13. Bicarburet Of Hydrogen

14. Benzolene

15. Benzin

16. [6]annulene

17. Motor Benzol

18. Carbon Oil

19. Benzeen

20. Benzolo

21. Fenzen

22. Nitration Benzene

23. (6)annulene

24. Benzol 90

25. Nci-c55276

26. Rcra Waste Number U019

27. Benzinum

28. 1,3,5-cyclohexatriene

29. Nsc 67315

30. Un 1114

31. Chebi:16716

32. Chembl277500

33. Mfcd00003009

34. Nsc-67315

35. J64922108f

36. Benzeen [dutch]

37. Benzen [polish]

38. Fenzen [czech]

39. Benzolo [italian]

40. Bnz

41. Benzine (obs.)

42. Benzin (obs.)

43. Caswell No. 077

44. Benzol Diluent

45. Benzene 100 Microg/ml In Methanol

46. Benzene, Acs Reagent, >=99.0%

47. Benzene, Pure

48. Ccris 70

49. 54682-86-9

50. Hsdb 35

51. Einecs 200-753-7

52. Un1114

53. Epa Pesticide Chemical Code 008801

54. Benzolum

55. Aromatic Alkane

56. Benzene (including Benzene From Gasoline)

57. P-benzene

58. Benzene Solution

59. Benzene-

60. Ai3-00808

61. C6h6

62. 26181-88-4

63. 1hyz

64. 1swi

65. Unii-j64922108f

66. [6]-annulene

67. Benzene Acs Grade

68. Benzene, For Hplc

69. {[6]annulene}

70. Ph-h

71. Phenyl; Phenyl Radical

72. 2z9g

73. 4i7j

74. Benzene [vandf]

75. Benzinum [hpus]

76. Benzene + Aniline Combo

77. Benzene [hsdb]

78. Benzene [iarc]

79. Benzene (benzol)

80. Benzene [mi]

81. Benzene [mart.]

82. Dsstox_cid_135

83. Benzene, Labeled With Carbon-14 And Tritium

84. Wln: Rh

85. Benzene [usp-rs]

86. Benzene [who-dd]

87. Epitope Id:116867

88. Benzene, Purification Grade

89. Ec 200-753-7

90. Benzene, Analytical Standard

91. Dsstox_rid_79433

92. Benzene, Lr, >=99%

93. Dsstox_gsid_39242

94. Ghl.pd_mitscher_leg0.503

95. Benzene, Anhydrous, 99.8%

96. Benzene, Ar, >=99.5%

97. Dtxsid3039242

98. 3,4-dnh

99. 1l83

100. 220l

101. 223l

102. Benzene 10 Microg/ml In Methanol

103. Zinc967532

104. Trans-n-methylphenylcyclopropylamine

105. Act02832

106. Bcp26158

107. Benzene 20 Microg/ml In Triacetin

108. Benzene, For Hplc, >=99.8%

109. Benzene, For Hplc, >=99.9%

110. Nsc67315

111. Tox21_202487

112. 1,3-cyclohexadiene-5,6-diylradical

113. Bdbm50167939

114. Bm 613

115. Stl264205

116. Benzene 1000 Microg/ml In Methanol

117. Benzene 5000 Microg/ml In Methanol

118. Benzene, Purum, >=99.0% (gc)

119. Akos008967253

120. Benzene, Saj First Grade, >=99.0%

121. Cas-71-43-2

122. Acetone Impurity C [ep Impurity]

123. Benzene [un1114] [flammable Liquid]

124. Benzene, Jis Special Grade, >=99.5%

125. Erythro-phenyl-2-piperidyl-carbinol,(-)

126. Ncgc00090744-01

127. Ncgc00090744-02

128. Ncgc00163890-01

129. Ncgc00163890-02

130. Ncgc00260036-01

131. Trans-n, N-dimethylphenylcyclopropylamine

132. Cc-34,(+/-)

133. Rng

134. Ds-002542

135. B0020

136. Ft-0622636

137. Ft-0622637

138. Ft-0622667

139. Ft-0627856

140. Ft-0657604

141. Q0038

142. Q2270

143. Benzene 30 Microg/ml In N,n-dimethylacetamide

144. Benzene, Acs Spectrophotometric Grade, >=99%

145. C01407

146. Benzene, Reagentplus(r), Thiophene Free, >=99%

147. Benzene, Puriss. P.a., Reag. Ph. Eur., >=99.7%

148. Q26841227

149. Z57120059

150. Biperiden Hydrochloride Impurity F [ep Impurity]

151. Benzene, For Residue Analysis, Suitable For 5000 Per Jis

152. Benzene, Suitable For 300 Per Jis, >=99.5%, For Residue Analysis

153. Benzene, Pharmaceutical Secondary Standard; Certified Reference Material

154. Benzene, Suitable For 1000 Per Jis, >=99.5%, For Residue Analysis

155. Benzene, Puriss., Absolute, Over Molecular Sieve (h2o <=0.005%), >=99.5% (gc)

156. 25053-22-9

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 78.11 g/mol
Molecular Formula C6H6
XLogP32.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass78.0469501914 g/mol
Monoisotopic Mass78.0469501914 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count6
Formal Charge0
Complexity15.5
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

MEDICATION (VET): Has been used as a disinfectant. /Former Use/

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 188


4.2 Drug Warning

Protected intercourse may be prudent following high exposure to benzene. As well, nursing mothers may be advised to discontinue nursing for 5 days following high exposure.

Zenz, C., O.B. Dickerson, E.P. Horvath. Occupational Medicine. 3rd ed. St. Louis, MO., 1994, p. 712


4.3 Minimum/Potential Fatal Human Dose

Immediately dangerous to life and health = 500 ppm

Sullivan, J.B., Krieger G.R. (eds). Clinical Environmental Health and Toxic Exposures. Second edition. Lippincott Williams and Wilkins, Philadelphia, Pennsylvania 1999., p. 754


... It has been estimated that 5-10 minutes of exposure to 20,000 ppm benzene in air is usually fatal.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Benzene p.30 PB2008-100004 (2007). Available from, as of August 12, 2014: https://www.atsdr.cdc.gov/toxprofiles/index.asp


Estimated oral doses from 9-30 g have proved fatal.

WHO; Environmental Health Criteria 150: Benzene p.46 (1993)


Single exposures to concentrations of 66,000 mg/cu m (20,000 ppm) commercial benzene have been reported to be fatal in man within 5-10 minutes. At lower levels, loss of consciousness, irregular heart-beat, dizziness, headache and nausea are observed.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V29 116 (1982)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Benzene is readily absorbed via lung, & about 40-50% is retained. ... It is taken up preferentially by fatty & nervous tissues, & about 30-50% ... is excreted unchanged via lung; a 3-phase excretion pattern is seen at ... /approx/ 0.7-1.7 hr, 3-4 hr, & 20-30 hr.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V7 211 (1974)


When benzene was placed on skin under closed cup it was absorbed at rate of 0.4 mg/sq cm/hr (Hanke et al 1961) ...

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V29 117 (1982)


Mice treated SC with 2 mL (3)H-labeled benzene/kg contained irreversibly bound radioactivity with decreasing binding magnitude in the following organs: liver, brain, kidney, spleen, fat. Mice treated with 2 daily SC doses of 0.5 mL (3)H-benzene/kg for 1-10 days showed a radioactivity binding with liver & bone marrow residues which increased with treatment duration, except in the case of binding to bone marrow which decreased after day 6.

PMID:663402 Snyder R et al; Res Commun Chem Pathol Pharmacol 20 (1): 191-4 (1978)


When administered to mice subcutaneously, 72% of dose is recovered in expired air.

PMID:849319 Andrews LS et al; Biochem Pharmacol 26: 293 (1977)


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


5.2 Metabolism/Metabolites

The major metabolitesof benzene metabolism are phenol, hydroquinone, and catechol. These metabolites are interactive and can affect the rate of each other's metabolism because they are substrates for the P-450 enzyme system. The route of exposure has little effect on the subsequent metabolism of benzene to hemotoxic metabolites.

Sullivan, J.B., Krieger G.R. (eds). Clinical Environmental Health and Toxic Exposures. Second edition. Lippincott Williams and Wilkins, Philadelphia, Pennsylvania 1999., p. 754


Metabolic products in rat ... are phenol, hydroquinone, catechol, hydroxyhydroquinone, & phenylmercapturic acid. Conjugated phenols have been reported ... except for a small amt of free phenol, all the phenolic metabolites were excreted in conjugated form. When (3)H-benzene was admin to mice, (3)H2O was also recovered from urine.

National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 688


Yields N-acetyl-S-phenyl-cysteine in rat. Yields benzyl alcohol in guinea pigs. ... Yields cis-1,2-dihydro-1,2-dihydroxybenzene in pseudomonas. Phenol in pseudomonas & achromobacter. Yields cis,cis-muconic acid in rabbit. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. B-4


In the rabbit, the major hydroxylation product of benzene was phenol, which along with some catechol and hydroquinone, was found in the urine conjugated with ethereal sulfate or glucuronic acid.

USEPA; Ambient Water Quality Criteria: Benzene p.C-11 (1980) EPA 440/5-80-018


For more Metabolism/Metabolites (Complete) data for BENZENE (26 total), please visit the HSDB record page.


Benzene has known human metabolites that include phenol.

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


5.3 Biological Half-Life

Whole body: 9-24 hours; however, up to 90 hours due to distribution in fat; [TDR, p. 154]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 154


The excretion of unchanged benzene from the lung of rats was reported to be biphasic, suggesting a two-compartment model for distribution and a half-life of 0.7 hr. This agreed with experimental half-life values for various tissues that ranged from 0.4 to 1.6 hr.

Rickert DE et al; Toxicol Appl Pharmacol 49: 417 (1979) as cited in USEPA; Ambient Water Quality Criteria: Benzene p.C-11 (1980) EPA 440/5-80-018


... The half-time of benzene in /high lipid content/ tissues is approximately 24 hours.

Zenz, C., O.B. Dickerson, E.P. Horvath. Occupational Medicine. 3rd ed. St. Louis, MO., 1994, p. 146


5.4 Mechanism of Action

Covalent interaction of a benzene metabolite with dna was shown in vivo, but no information was given about the chem nature of this metabolite. A likely intermediate in benzene metabolism is benzene oxide. In neutral aq media it rearranges only slowly to the phenol so that its lifetime could be long enough for diffusion from the site of activation to the dna. Alternatively, the metabolic appearance of polyhydroxy derivatives suggests the formation of a phenol epoxide, so that the reactive molecule could be a secondary metabolite.

PMID:890848 Lutz WK, Schlatter C; Chem Biol Interact 18 (2): 241-6 (1977)


The available evidence supports the concept that benzene toxicity is caused by one or more metabolites of benzene. ... Benzene metabolites containing 2 or 3 hydroxyl groups inhibited mitosis. Toluene, which inhibits benzene metabolism, protected animals against benzene-induced myelotoxicity. Benzene toxicity could be correlated with the appearance of benzene metabolites in bone marrow. Although it is clear that benzene can be metabolized in bone marrow, the observation that partial hepatectomy protects against benzene toxicity suggests that a metabolite formed in liver is essential for benzene toxicity.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V29 113 (1982)


... Importance of polyhydroxylated derivatives of benzene & their semiquinones. ... /It has been/ shown that hydroquinone inhibits rat brain microtubule polymerization; that hydroquinone & para-benzoquinone are the most potent inhibitors of T- & B-lymphocyte function, as measured in mouse spleen cells in culture; that hydroquinone inhibits lectin-stimulated lymphocyte agglutination in rat spleen prepn in vitro; & that para-benzoquinone is the metabolite most likely to be responsible for suppression of lymphocyte transformation & microtubule assembly in rat spleen cells in culture. However, admin of these cmpd to animals does not produce the typical picture of benzene toxicity ... admin /of/ major metabolites of benzene to mice ... failed to ... decr ... red blood cell production, using the (59)Fe uptake technique ... /it's been/ suggested that ring-opening products may play a role in benzene toxicity. ... In mice benzene treatment suppressed subsequent colony forming unit-C formation from bone-marrow cells in vitro. Treating the animals with phenol, hydroquinone or benzene dihydrodiol failed to suppress colony forming unit-C. Thus, the toxic metabolites of benzene have yet to be identified.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V29 113 (1982)


... Radioactivity /has been demonstrated/ in a nucleic acid fraction from rat liver following admin of either (3)h- or (14)C-labelled benzene. It has been shown that benzene binds covalently to protein in liver, bone marrow, kidney, lung, spleen, blood, & muscle. Less covalent binding was observed to the protein of bone marrow, blood, & spleen of C57Bl/6 mice, which are more resistant to the benzene-induced effects on red cell production, than to that of sensitive DBA/2 mice. ... Covalent binding of benzene to protein in perfused bone-marrow prepn /has been demonstrated/. ... A metabolite of phenol binds to liver protein more efficiently than does benzene oxide, & they have electrophoretically separated hepatic proteins to which benzene preferentially binds. ... Covalent binding to mitochondria is a prominent feature of benzene metabolism. ... There is relatively more radioactivity in a nucleic acid-rich fraction of a benzene metabolite isolated from mouse bone-marrow cells than in a similar fraction from liver.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V29 113 (1982)


For more Mechanism of Action (Complete) data for BENZENE (12 total), please visit the HSDB record page.