Methallyl chloride

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]

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, P261, 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

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]

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