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Methallyl chloride

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(Redirected from 3-Chloro-2-methylpropene)
Methallyl chloride
Names
Preferred IUPAC name 3-Chloro-2-methylprop-1-ene
Other names Isobutenyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.411 Edit this at Wikidata
EC Number
  • 209-251-2
KEGG
PubChem CID
RTECS number
  • UC8050000
UNII
UN number 2554
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H7Cl/c1-4(2)3-5/h1,3H2,2H3Key: OHXAOPZTJOUYKM-UHFFFAOYSA-N
SMILES
  • CC(=C)CCl
Properties
Chemical formula C4H7Cl
Molar mass 90.55 g·mol
Appearance Colorless liquid
Density 0.9210 g/cm (15 °C)
Boiling point 71–72 °C (160–162 °F; 344–345 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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 , 100 kPa). Infobox references
Chemical compound

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.

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.

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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