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Alyl chloride oxide
Also known as: 2-(chloromethyl)oxirane, 106-89-8, Epichlorhydrin, 1-chloro-2,3-epoxypropane, Oxirane, (chloromethyl)-, Glycidyl chloride
Molecular Formula
C3H5ClO
Molecular Weight
92.52  g/mol
InChI Key
BRLQWZUYTZBJKN-UHFFFAOYSA-N
FDA UNII
08OOR508C0

A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.
1 2D Structure

Alyl chloride oxide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(chloromethyl)oxirane
2.1.2 InChI
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
2.1.3 InChI Key
BRLQWZUYTZBJKN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1C(O1)CCl
2.2 Other Identifiers
2.2.1 UNII
08OOR508C0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Epichlorhydrin

2. Epichlorohydrin, (+-)-isomer

3. Epichlorohydrin, (s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 2-(chloromethyl)oxirane

2. 106-89-8

3. Epichlorhydrin

4. 1-chloro-2,3-epoxypropane

5. Oxirane, (chloromethyl)-

6. Glycidyl Chloride

7. Epichlorhydrine

8. Chloromethyloxirane

9. 1,2-epoxy-3-chloropropane

10. 2,3-epoxypropyl Chloride

11. Chloropropylene Oxide

12. 3-chloro-1,2-epoxypropane

13. Glycerol Epichlorhydrin

14. Epichloorhydrine

15. Glycerol Epichlorohydrin

16. 3-chloropropylene Oxide

17. (chloromethyl)ethylene Oxide

18. (chloromethyl)oxirane

19. Epicloridrina

20. 3-chloro-1,2-propylene Oxide

21. Epichlorohydryna

22. Epichlorophydrin

23. Alpha-epichlorohydrin

24. Epi-chlorohydrin

25. 3-chloropropene-1,2-oxide

26. Skekhg

27. (+/-)-epichlorohydrin

28. Oxirane, 2-(chloromethyl)

29. 2-chloromethyl-oxirane

30. Epoxypropyl Chloride

31. Gamma-chloropropylene Oxide

32. Propane, 1-chloro-2,3-epoxy-

33. 1-chlor-2,3-epoxy-propan

34. 1-cloro-2,3-epossipropano

35. 1-chloor-2,3-epoxy-propaan

36. Rcra Waste Number U041

37. (+/-)-2-(chloromethyl)oxirane

38. Allyl Chloride Oxide

39. (rs)-3-chloro-1,2-epoxypropane

40. Dl-a-epichlorohydrin

41. Epoxy-3-chloropropane

42. (chloromethyl)-oxirane

43. Chloropropylene

44. .alpha.-epichlorohydrin

45. Epichlorohydrine

46. Nsc 6747

47. Alyl Chloride Oxide

48. Chloropropyl Epoxide

49. .gamma.-chloropropylene Oxide

50. (dl)-.alpha.-epichlorohydrin

51. Oxirane,(chloromethyl)-

52. Chloro-1,2-epoxypropane

53. Chloro-2,3-epoxypropane

54. Chloropropene-1,2-oxide

55. 3-chloro-propylene Oxide

56. 2-(chloromethyl)-oxirane

57. Chloro-1,2-propylene Oxide

58. 1-chloro-2,3-epoxy-propane

59. 1-chloro-2,3-epoxy Propone

60. Chebi:37144

61. 08oor508c0

62. Nsc-6747

63. Mfcd00005132

64. Oxirane, (chloromethyl)-, Homopolymer

65. Ncgc00091792-01

66. Dsstox_cid_566

67. Epichlorohydrin, >=99%

68. Dsstox_rid_75662

69. Dsstox_gsid_20566

70. 13403-37-7

71. 9009-12-5

72. Ech

73. Caswell No. 424

74. Epicloridrina [italian]

75. Epichloorhydrine [dutch]

76. Epichlorhydrine [french]

77. Epichlorohydryna [polish]

78. Cas-106-89-8

79. Hsdb 39

80. Ccris 277

81. 3-chloropropyl Epoxide

82. Nci-c07001

83. 5-17-01-00020 (beilstein Handbook Reference)

84. Einecs 203-439-8

85. Un2023

86. 1-chlor-2,3-epoxy-propan [german]

87. Rcra Waste No. U041

88. 1-chloor-2,3-epoxy-propaan [dutch]

89. 1-cloro-2,3-epossipropano [italian]

90. Epa Pesticide Chemical Code 097201

91. Brn 0079785

92. Epichiorohydrin

93. (chloromethyl) Ethylene Oxide

94. Unii-08oor508c0

95. Ai3-03545

96. Epi-chlorohydrine

97. A-epichlorohydrin

98. Epichloro Hydrine

99. (rs)-epichlorohydrin

100. (+) Epichlorohydrin

101. (-) Epichlorohydrin

102. 2-chloromethyloxirane

103. (?)-epichlorohydrin

104. Chloromethyl) Oxirane

105. Poly(epichlorohydrin)

106. (rac)-epichlorohydrin

107. Racemic Epichlorohydrin

108. Beta-epoxypropylchloride

109. Racemic Epichlorohydrine

110. Epichlorohydrin, 99%

111. Poly(chloromethyloxirane)

112. 2-(chloromethyl) Oxirane

113. Epichlorohydrin Homopolymer

114. Bmse000722

115. Ec 203-439-8

116. Wln: T3otj B1g

117. (dl)-alpha-epichlorohydrin

118. (rs)-(chloromethyl)oxirane

119. Epichlorohydrin [mi]

120. Epichlorohydrin Reagent Grade

121. Oxirane, 2-(chloromethyl)-

122. Epichlorohydrin [hsdb]

123. Epichlorohydrin [iarc]

124. Epichlorohydrin [inci]

125. E181 [russian Epoxy Resin]

126. E 181 [russian Epoxy Resin]

127. Epichlorohydrin [mart.]

128. Chembl1421613

129. Dtxsid1020566

130. Nsc6747

131. (chloromethyl)oxirane, Homopolymer

132. Amy40813

133. Tox21_111167

134. Tox21_200276

135. Stl163564

136. (+/-)-1-chloro-2,3-epoxypropane

137. Akos000118974

138. Akos016039400

139. Epichlorohydrin [un2023] [poison]

140. Sb11597

141. Sb11598

142. Un 2023

143. Ncgc00091792-02

144. Ncgc00091792-03

145. Ncgc00257830-01

146. Bp-31004

147. Bp-31046

148. (+/-)-epichlorohydrin, Analytical Standard

149. Db-018066

150. Epichlorhydrin 1000 Microg/ml In Methanol

151. Epichlorhydrin 100 Microg/ml In Cyclohexane

152. Ft-0605064

153. Ft-0605270

154. Ft-0625672

155. Ft-0667883

156. Epichlorhydrin 100 Microg/ml In Acetonitrile

157. (+/-)-epichlorohydrin, Purum, >=99% (gc)

158. Q423083

159. (+/-)-epichlorohydrin, Puriss., >=99.5% (gc)

160. Q-201062

161. F0001-0128

162. Z955123632

163. (+/-)-2-(chloromethyl)oxirane, 1-chloro-2,3-epoxypropane

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 92.52 g/mol
Molecular Formula C3H5ClO
XLogP30.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass92.0028925 g/mol
Monoisotopic Mass92.0028925 g/mol
Topological Polar Surface Area12.5 Ų
Heavy Atom Count5
Formal Charge0
Complexity37.9
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

WITH EXCEPTION OF PANCREAS, A CORRELATION OBSERVED BETWEEN TISSUE DISTRIBUTION & TARGET ORGAN TOXICITY. EXCRETION MAINLY IN URINE. 21 & 18% OF DOSE EXCRETED AS CO2 IN MALE & FEMALE RATS. PEAK TISSUE LEVELS IN FEMALES LOWER.

WEIGEL WW ET AL, RES COMMUN CHEM PATHOL PHARMACOL 20 (2): 275 (1978)


/EPICHLOROHYDRIN MAY BE/ ABSORBED THROUGH THE SKIN.

Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981.


The upper respiratory tracts of male Fischer F344 rats were surgically isolated and connected to a specially designed flow system. The tracheal connection of the upper respiratory tract and the lower respiratory tract was interrupted. The upper respiratory tract was exposed to propylene-glycol- monomethyl ether, propylene glycol monomethyl ether acetate, epichlorohydrin, cmpd which include vapors while the rat spontaneously breathed from a stream of air. Intact rats were exposed nose only to the same compound and the percentages of vapor absorbed were determined for comparison purposes. Attempts were made to correlate the results with the water solubility of the compounds. The data were compared to predictions of two compartment mathematical models. More than 50 to 70% of the epichlorohydrin, vapors passing through the isolated upper respiratory tacts were absorbed. With the exception of styrene and methylene chloride, the percentage of vapors absorbed by the upper respiratory tract approximated that observed in the lower respiratory tract and nose only exposed animals. There was no correlation between absorption in the URT and water solubility. The mathematical models generally predicted the absorption of vapors by the lower respiratory tract and intact animals accurately. The models seriously underestimated absorption of epichlorohydrin, by the upper respiratory tract. /Results indicate/ that blood air partitioning can account for absorption of chemicals by the upper respiratory tract, but only if other metabolic and physiological parameters are considered.

Stott Wt et al, eds; Conf. on Toxicology of Nasal Passages: Chemical Industry Institute Toxicology Series p.191-210 (1986)


The highest tissue concentrations in rodents were found in the nose after inhalation, and in the stomach after ingestion. In rats, regardless of the route of exposure, most absorbed epichlorohydrin is metabolized rapidly, part being excreted as carbon dioxide via the lungs and part as water-soluble compounds via the urine.

IPCS; Health and safety guide No. 8 on Epichlorohydrin (1987). Available from, as of March 9, 2009: https://www.inchem.org/documents/hsg/hsg/hsg008.htm


For more Absorption, Distribution and Excretion (Complete) data for EPICHLOROHYDRIN (7 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

... WISTAR RATS DOSED ORALLY OR IP WITH ... EPICHLOROHYDRIN YIELD ... URINARY METABOLITES ... 2,3-DIHYDROXYPROPYL-S-CYSTEINE & ITS N-ACETATE. SINCE EPICHLOROHYDRIN IS A STRONG ELECTROPHILE THAT IS CAPABLE OF REACTING WITH CELLULAR NUCLEOPHILES, IT IS PROBABLE THAT SOME EPICHLOROHYDRIN METABOLITES ARE ALSO COVALENTLY BOUND TO VARIOUS TISSUE MACROMOLECULES.

National Research Council. Drinking Water and Health. Volume 3. Washington, DC: National Academy Press, 1980., p. 113


Rats given oral (14)C labeled epichlorhydrin and sacrificed after 3 days: 38% exhaled as carbon dioxide; 50% excreted as metabolites in urine; 3% excreted in the feces; and the remainder was found in the tissues - liver, kidney, and forestomach.

Gingell R et al; Drug Metb Dispos 13 (3): 333-41 (1985)


The major urinary metabolite of (14)C-epichlorohydrin, after oral administration to rats, was identified previously to be N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine at 36% of the administered dose. In a similar study reported here, 1,2-dibromo-3- chloropropane was metabolized to at least 20 radioactive urinary metabolites. N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine was only a minor metabolite (4%) of 1,2-dibromo-3-chloropropane. Epichlorohydrin was metabolized in vitro by rat liver microsomes to alpha-chlorohydrin, but 1,2-dibromo-3-chloroproane was not metabolized to epichlorohydrin or alpha-chlorohydrin under similar conditions. Covalent binding of radioactivity to liver microsomal proteins occurred for both substrates, but was less for (14)C-epichlorohydrin than for (14)C-1,2-dibromo-3-chloropropane. Addition of 3,3,3-trichloropropylene oxide, an inhibitor of epoxide hydrolase, increased the extent of protein binding of epichlorohydrin, but decreased the amojnt of (14)C-1,2-dibromo-3-chloropropane which was bound. The data indicate the epichlorohydrin is not a significant in vivo nor in vitro metabolite of 1,2-dibromo-3-chloropropane in the rat, and is unlikely to be responsible for the toxicity of 1,2-dibromo-3-chloropropane.

PMID:3564537 Gingell R et al; Xenobiotica 17 (2): 229-40 (1987)


In in vitro studies, it was shown that epichlorohydrin was hydrolyzed into 3-chloro-1,2-propanediol by the microsomal epoxide hydrolase(s) (EC 3.3.2.3) of mouse liver in the absence of NADPH, the roles of protein or glutathione in this detoxification being insignificant.

WHO; Environmental Health Criteria Document No. 33: Epichlorohydrin (106-89-8). Available from, as of March 9, 2009: https://www.inchem.org/documents/ehc/ehc/ehc33.htm


For more Metabolism/Metabolites (Complete) data for EPICHLOROHYDRIN (7 total), please visit the HSDB record page.


4.3 Biological Half-Life

No reports found; [TDR, p. 619]

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. 619


... Male mice were given a single ip injection of epichlorohydrin dissolved in corn oil. Groups of ten mice were killed by decapitation at 1, 3, 5, 7, 10, 15, 20 and 30 minutes after injection and blood samples were collected. The in vivo half-life of epichlorohydrin is extremely short, being only just detectable after 15 minutes.

USEPA; Health Assessment Document: Epichlorohydrin p.4-2 (1983) EPA 600/8-83-032A


Half-life values of ECH and its metabolite, alpha-chloro-hydrin, in the blood of Swiss-Albino mice, which has been administered 200 mg/kg bw doses of the substances (oral or ip) were found to be 3.6-5.3 and 65 minutes.

European Commission, ESIS; IUCLID Dataset, 1-chloro-2,3-epoxypropane (106-89-8) p 75 (2000 CD-ROM edition). Available from, as of March, 4 2009: https://esis.jrc.ec.europa.eu/


4.4 Mechanism of Action

The two reactive electrophilic sites, the C-1 carbon in the epoxide ring and C-3, the chlorine-bearing carbon, behave as alkylating agents and can react nonenzymatically with glutathione or protein sulfhydryl groups.

USEPA; Health Assessment Document: Epichlorohydrin p.4-6 (1983) EPA 600/8-83-032A


3-Chloroglycerophosphate inhibited rat sperm enzyme activities (glyceraldehyde-3-phosphate dehydrogenase and triosephosphate isomerase) and hence glycolysis. Only the S(-) isomer and not the R(+) isomer of 3-chloro-1,2-propanediol produced antifertility or antiglycolytic effects. Since epichlorohydrin has not been shown to have enzyme inhibitory effects, it may be that it is metabolized in vivo to S(-) alpha-chlorohydrin phosphate, to exert its antifertility effect.

USEPA; Health Assessment Document: Epichlorohydrin p.4-8 (1983) EPA 600/8-83-032A


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