Talk:Epichlorohydrin

Chirality

Epichlorohydrine is a chiral compound and exists in pure enantiomeric forms - R(-) CAS Nr. [67843-74-7] and S(+) CAS Nr. [51594-55-9], as well as a racemate, CAS Nr. [106-89-8]. One should elaborate this. —Preceding unsigned comment added by 87.110.241.125 (talk) 00:33, 11 March 2008 (UTC)[reply]

Origin of compound and its name

Part of the edit-summary for this edit, which added a comment that the called "epichlorohydrin" is not a "chlorohydrin", notes "Does anyone understand why it is called epichlorohydrin?" Something like that might be mentioned in the early literature that mentions this compound. The early history of it is completely absent from our article (when was it first discovered/synthesized and why, etc.). DMacks (talk) 08:22, 5 June 2014 (UTC)[reply]

Looking at the oldest refs in SciFinder for this chemical, it appears that the name parses approximately as "epi...hydrin". That is, it's like a ...hydrin, but the epoxide derivative/analog thereof. Best very-old-ref I see is doi:10.1021/ja02071a003 (1898, by which time this various epi...hydrin chemicals were already known). It has 1-chloro-2,3-dihydroxypropane as "monochlorohydrin" and 1-thiocyano-2,3-dihydroxypropane as "α-thiocyanhydrin" (and various other thiocyanohydrins similarly), and then 1-thiocyano-2,3-epoxypropane as an "epithiocyanhydrin". DMacks (talk) 18:10, 16 June 2014 (UTC)[reply]