1,1-Bis(chloromethyl)ethylene

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
CAS Number	1871-57-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL160833;
ChemSpider	15073;
ECHA InfoCard	100.015.900
EC Number	217-489-3;
PubChem CID	15859;
UNII	1XTP1GFW2A;
CompTox Dashboard (EPA)	DTXSID3022166 ;
	InChI InChI=1S/C4H6Cl2/c1-4(2-5)3-6/h1-3H2 Key: XJFZOSUFGSANIF-UHFFFAOYSA-N;
	SMILES C=C(CCl)CCl;
Properties
Chemical formula	C4H6Cl2
Molar mass	124.99 g·mol−1
Appearance	Colorless liquid
Density	1.1782 g/cm3
Melting point	−14 °C (7 °F; 259 K)
Boiling point	138 °C (280 °F; 411 K)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	alkylating agent
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H315, H319, H335, H400
Precautionary statements	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

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.

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

^ ^a ^b 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.
^ 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.
^ Mondanaro, Kathleen R.; Dailey, William P (1998). "3-CHLORO-2-(CHLOROMETHYL)-1-PROPENE". Organic Syntheses. 75: 89. doi:10.15227/orgsyn.075.0089.

[temps-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.

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