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
Preferred IUPAC name
3-Chloro-2-(chloromethyl)prop-1-ene
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
  • InChI=1S/C4H6Cl2/c1-4(2-5)3-6/h1-3H2
    Key: XJFZOSUFGSANIF-UHFFFAOYSA-N
  • C=C(CCl)CCl
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
Occupational safety and health (OHS/OSH):
Main hazards
 alkylating agent
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H226, H301, H315, H319, H335, H400
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
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 (14): 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.open access
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