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
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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