Crotyl chloride
| Names | |
|---|---|
| Preferred IUPAC name
(2E)-1-Chlorobut-2-ene | |
| Other names
1-Chloro-2-butene, 1-chlorobut-2-ene, 2-butenyl chloride, gamma-methylallyl chloride
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| Identifiers | |
3D model (JSmol)
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| 605304 | |
| ChemSpider | |
| ECHA InfoCard | 100.008.855 |
PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C4H7Cl | |
| Molar mass | 90.55 g·mol−1 |
| Appearance | Liquid |
| Density | 0.949 g/cm3 |
| Melting point | −65 °C (−85 °F; 208 K) |
| Boiling point | 84 °C (183 °F; 357 K) |
| Vapor pressure | 37084 mmHG |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | −15 °C (5 °F; 258 K) |
| 510 °C (950 °F; 783 K) | |
| Related compounds | |
Related chloroalkenes
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Allyl chloride Methallyl chloride |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Crotyl chloride is an organochloride with the molecular formula C4H7Cl or H3C(CH)2CH2Cl.[1] It is a derivative of 2-butene with a chlorine atom at a terminal carbon. It exhibits cis-trans isomerism about the double bond; the (E) isomer predominates in commercial preparations.[2]
Preparation
It can be produced by the chlorination of crotyl alcohol by chlorinating agents such as triphenylphosphine dichloride.[2]
Applications
Treatment of crotyl halides with magnesium produces crotyl Grignard reagents. The chloride is more stable than the bromide.[3] These reagents can then be used in the Grignard reaction for crotylation of carbonyl compounds.[4]
Dehydrohalogenation of crotyl chloride was once used as a laboratory route to produce butadiene, though the pyrolysis of cyclohexene is preferred according to Organic Syntheses.[5] Crotyl chloride may be used as a model compound for other allylic hydrochlorocarbons.[6]
References
- ^ NIST Web Book
- ^ a b d'Angelo, Lihong L. (2001). "Crotyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc254. ISBN 0-471-93623-5.
- ^ Florio, Saverio; Capriati, Vito (2001). "Crotylmagnesium Bromide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc258. ISBN 0-471-93623-5.
- ^ Matsukawa, Satoru; Funabashi, Yohei; Imamoto, Tsuneo (2003). "Regioselective allylation reactions using crotyl Grignard reagent–CeCl3 systems". Tetrahedron Letters. 44 (5): 1007–1010. doi:10.1016/S0040-4039(02)02741-7.
- ^ E. B. Hershberg and John R. Ruhoff (1937). "1,3-butadiene". Organic Syntheses. 17: 25.
- ^ Purmova, Jindra; Pauwels, Kim F. D.; Van Zoelen, Wendy; Vorenkamp, Eltjo J.; Schouten, Arend J.; Coote, Michelle L. (2005). "New Insight into the Formation of Structural Defects in Poly(Vinyl Chloride)". Macromolecules. 38 (15): 6352–6366. Bibcode:2005MaMol..38.6352P. doi:10.1021/ma050035p. hdl:11370/e7d9787c-d322-4ffe-8ba9-15cdf777e0ca.