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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.411
EC Number
  • 209-251-2
KEGG
RTECS number
  • UC8050000
UNII
UN number 2554
  • InChI=1S/C4H7Cl/c1-4(2)3-5/h1,3H2,2H3
    Key: OHXAOPZTJOUYKM-UHFFFAOYSA-N
  • CC(=C)CCl
Properties
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:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H225, H302, H314, H317, H331, H335, H336, H351, H361, H372, H373, H411
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)
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]

References
  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.
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