Methallyl chloride

Methallyl chloride
Names
	Preferred IUPAC name 3-Chloro-2-methylprop-1-ene
	Other names Isobutenyl chloride
Identifiers
CAS Number	563-47-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82419;
ChEMBL	ChEMBL157368;
ChemSpider	21106501;
ECHA InfoCard	100.008.411
EC Number	209-251-2;
KEGG	C19363;
PubChem CID	11241;
RTECS number	UC8050000;
UNII	7A9X1C3I3O;
UN number	2554
CompTox Dashboard (EPA)	DTXSID1020279 ;
	InChI InChI=1S/C4H7Cl/c1-4(2)3-5/h1,3H2,2H3 Key: OHXAOPZTJOUYKM-UHFFFAOYSA-N;
	SMILES CC(=C)CCl;
Properties
Chemical formula	C4H7Cl
Molar mass	90.55 g·mol−1
Appearance	Colorless liquid
Density	0.9210 g/cm3 (15 °C)
Boiling point	71–72 °C (160–162 °F; 344–345 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314, H317, H331, H335, H336, H351, H361, H372, H373, H411
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P272, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P330, P333+P313, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	−12 °C (10 °F; 261 K)
Autoignition; temperature	540 °C (1,004 °F; 813 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methallyl chloride is the organic compound with the formula CH₂=C(CH₃)CH₂Cl. It is a colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups.^[1]

Reactivity

It is also a precursor to methallyl ligand. It is an isomer of crotyl chloride.

Methylenecyclopropane can be synthesised via an intramolecular cyclisation reaction from methallyl chloride by treatment with a strong base such as sodium amide.^[2]

References

^ Krook, Mark A.; O'Doherty, George A.; Gao, Dong (2007). "Methallyl chloride". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–6. doi:10.1002/9780470842898.rm061.pub2. ISBN 978-0471936237.
^ Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "Cyclobutanone from Methylenecyclopropane via Oxaspiropentane". Organic Syntheses. 57: 36. doi:10.15227/orgsyn.057.0036.

[1] Krook, Mark A.; O'Doherty, George A.; Gao, Dong (2007). "Methallyl chloride". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–6. doi:10.1002/9780470842898.rm061.pub2. ISBN 978-0471936237.

[2] Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "Cyclobutanone from Methylenecyclopropane via Oxaspiropentane". Organic Syntheses. 57: 36. doi:10.15227/orgsyn.057.0036.

[1]

[2]