Crotyl chloride

Last updated
Crotyl chloride
Crotyl chloride.svg
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
Identifiers
3D model (JSmol)
605304
ChemSpider
ECHA InfoCard 100.008.855 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • EM4264000
UNII
  • InChI=1S/C4H7Cl/c1-2-3-4-5/h2-3H,4H2,1H3/b3-2+
    Key: YTKRILODNOEEPX-NSCUHMNNSA-N
  • InChI=1/C4H7Cl/c1-2-3-4-5/h2-3H,4H2,1H3/b3-2+
    Key: YTKRILODNOEEPX-NSCUHMNNBH
  • C/C=C/CCl
Properties
C4H7Cl
Molar mass 90.55 g·mol−1
AppearanceLiquid
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)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
3
2
Flash point −15 °C (5 °F; 258 K)
510 °C (950 °F; 783 K)
Related compounds
Related chloroalkenes
 Allyl chloride
Methallyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Contents

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

  1. ↑ NIST Web Book
  2. 1 2 d'Angelo, Lihong L. (2001). "Crotyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc254. ISBN   0-471-93623-5.
  3. ↑ Florio, Saverio; Capriati, Vito (2001). "Crotylmagnesium Bromide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc258. ISBN   0-471-93623-5.
  4. ↑ 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.
  5. ↑ E. B. Hershberg and John R. Ruhoff (1937). "1,3-butadiene". Organic Syntheses . 17: 25.
  6. ↑ 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.