1,1-Bis(chloromethyl)ethylene

1,1-Bis(chloromethyl)ethylene
Names
	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)[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
GHS precautionary statements	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

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

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: 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.

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[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: 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.