1,1-Bis(chloromethyl)ethylene

1,1-Bis(chloromethyl)ethylene is the organic compound with the formula CH2=C(CH2Cl)2. It is a colorless liquid. Featuring two allylic chloride substituents, it is dialkylating agent.

1,1-Bis(chloromethyl)ethylene
Names
Other names
3-Chloro-2-(chloromethyl)propene, 1,1-Bis(chloromethyl)ethene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.900
EC Number
  • 217-489-3
UNII
Properties
C4H6Cl2
Molar mass 124.99 g·mol−1
Appearance Colorless liquid
Density 1.1782 g/cm3
Melting point −14 °C (7 °F; 259 K)[1]
Boiling point 138 °C (280 °F; 411 K)[1]
Hazards
Main hazards alkylating agent
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H301, H315, H319, H335, H400
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+310, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P370+378, P391
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

It is prepared from pentaerythritol via a multistep procedure, beginning with the partial chlorination.[2][3] The compound reacts with diiron nonacarbonyl to give the complex of trimethylenemethane Fe(η4-C(CH2)3)(CO)3. It is also a precursor to [1.1.1]-propellane.

References
  1. Mooradian, Aram; Cloke, J. B. (June 1945). "The Synthesis of 3-Chloro-2-chloromethyl-1-propene from Pentaerythritol". Journal of the American Chemical Society. 67 (6): 942–944. doi:10.1021/ja01222a019.
  2. Mondanaro Lynch, Kathleen; Dailey, William P. (1995). "Improved Preparations of 3-Chloro-2-(chloromethyl)-1-propene and 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane: Intermediates in the Synthesis of [1.1.1]Propellane". Journal of Organic Chemistry. 60: 4666-8. doi:10.1021/jo00119a057.
  3. Mondanaro, Kathleen R.; Dailey, William P (1998). "3-CHLORO-2-(CHLOROMETHYL)-1-PROPENE". Organic Syntheses. 75: 89. doi:10.15227/orgsyn.075.0089.
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