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Wikipedia

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
  • 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
  • 11241
RTECS number
  • UC8050000
UNII
  • 7A9X1C3I3O
UN number 2554
  • DTXSID1020279
  • 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:
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).

Reactivity edit

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 edit

  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.

methallyl, chloride, organic, compound, with, formula, ch2cl, colorless, liquid, lacrymator, properties, similar, those, allyl, chloride, strong, alkylating, agent, used, install, isobutenyl, groups, namespreferred, iupac, name, chloro, methylprop, eneother, n. 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 NamesPreferred IUPAC name 3 Chloro 2 methylprop 1 eneOther names Isobutenyl chlorideIdentifiersCAS Number 563 47 33D model JSmol Interactive imageChEBI CHEBI 82419ChEMBL ChEMBL157368ChemSpider 21106501ECHA InfoCard 100 008 411EC Number 209 251 2KEGG C19363PubChem CID 11241RTECS number UC8050000UNII 7A9X1C3I3OUN number 2554CompTox Dashboard EPA DTXSID1020279InChI InChI 1S C4H7Cl c1 4 2 3 5 h1 3H2 2H3Key OHXAOPZTJOUYKM UHFFFAOYSA NSMILES CC C CClPropertiesChemical formula C 4H 7ClMolar mass 90 55 g mol 1Appearance Colorless liquidDensity 0 9210 g cm3 15 C Boiling point 71 72 C 160 162 F 344 345 K HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H302 H314 H317 H331 H335 H336 H351 H361 H372 H373 H411Precautionary 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 P501Flash point 12 C 10 F 261 K Autoignitiontemperature 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 referencesReactivity editIt 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 nbsp References edit 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 Retrieved from https en wikipedia org w index php title Methallyl chloride amp oldid 1159819385, wikipedia, wiki, book, books, library,

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