Alpha-chlorohydrin

Slott VL, Jeffay SC, Suarez JD, Barbee RR, Perreault SD (1995) Synchronous assessment of sperm motility and fertilizing ability in the hamster following treatment with alpha-chlorohydrin. J Androl, 16 523-535. 

Stein et al. (1977) (Fig. 3), supposed the HCH hydroxylation to hexachlorocyclohexanols (I) to explain the polychlorophenol formation from HCH. This alpha-chlorohydrin (I) that results would be expected to eliminate spontaneously HCl to form a ketone, 2,3,4,5,6-pentachloro-cyclohexanone-(l) (II). An elimination of two pairs of H C1 in alpha beta-position to the keto-function yielding a symmetrical trichlorocyclo-hexadienone (III) now could be imaginable. Intermediate (III) could be stabilized by tautomerization to 2,4,6-TCP. The authors stated a high extent of conjugation (in vivo 90% ) of this TCP. 

Chemical/Physical. Chlorination of 2-chloroethyl vinyl ether to a-chloroethyl ethyl ether or P-chloroethyl ethyl ether may occur in water treatment facilities. The alpha compound is very unstable in water and decomposes almost as fast as it is formed (Summers, 1955). Although stable in NaOH solutions, in dilute acid solutions hydrolysis yields acetaldehyde and chlorohydrin (Windholz et al., 1983). At pH 7 and 25 °C, the hydrolysis half-life is 175 d (Jones and Wood, 1964). 

Cassidy, S.L., Dix, K.M. Jenkins, T. (1983) Evaluation of a testicular sperm head counting technique using rats exposed to dimethoxyethyl phthalate (DMEP), glycerol alpha-mono-chlorohydrin (GMCH), epichlorohydrin (ECH), formaldehyde (FA), or methyl methane-sulfonate (MMS). Arch. Toxicol., 53, 71-78... 

Chlorohydrins are compounds characterized by alpha halo-alpha alkoxy groups bound to a common carbon atom. These compounds undergo rapid hydrolysis at this shared carbon atom. Bis(2-chloroisopropyl)ether, a chlorohydrin, has two such carbon atoms, and both react very rapidly with water. In fact, the reactions are so fast that acid and alkaline contributions have not been determined. It is likely, however, that base accelerates the reaction kinetics. The proposed reaction pathway for this compound is based on the reported pathway for bis(chloroethyl)ether (Figure 13.4). The reported rate constant for bis(chlorome-thyl)ether, of 0.23 sec-1 was based on an observed half-life of a few minutes. Similarly, for bis(2-chloroisopropyl)ether, both of the chloro substituents are reactive, and a half-life of a few minutes can be assigned to this compound, as well. 

As indicated above, the majority of reactive oxygen species are capable of eliciting general lipid peroxidation reactions, where the products described so far do not give any indication of the reactive species involved. In contrast, the hypohalous acids show reactivity with membrane phospholipids, with the generation of specific haloamines and halohydrins. Specifically, hypohalous acids can add across an unsaturated C=C bond within a fatty acid chain to yield alpha beta chlorohydrin and bromohydrin isomers [8] as shown in Scheme 1. 

C3H7CIO2 96-24-2. alpha.-Glycerol chlorohydrin see 3-Chloropropan-l,2-diol... 

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