Methylcyclopentadiene

Methylcyclopentadiene

Left to right: 2-methyl-1,3-cyclopentadiene; 1-methyl-1,3-cyclopentadiene; 5-methyl-1,3-cyclopentadiene
Names
Other names
Cp′; MeCp
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.043.400 Edit this at Wikidata
EC Number
  • 1-methyl: 247-724-5
UNII
UN number 1993
  • 1-methyl: InChI=1S/C6H8/c1-6-4-2-3-5-6/h2-4H,5H2,1H3 checkY
    Key: NFWSQSCIDYBUOU-UHFFFAOYSA-N checkY
  • 2-methyl: InChI=1S/C6H8/c1-6-4-2-3-5-6/h2,4-5H,3H2,1H3
    Key: AHQZRFBZJSCKAV-UHFFFAOYSA-N
  • 5-methyl: InChI=1S/C6H8/c1-6-4-2-3-5-6/h2-6H,1H3
    Key: QVRBGKYLLCLCHL-UHFFFAOYSA-N
  • 1-methyl: C\1=C\C=C(\C)C/1
  • 2-methyl: C\1=C\C(\C)=CC/1
  • 5-methyl: C\1=C\C=CC/1(\C)
Properties
C6H8
Molar mass 80.130 g·mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H350, H410
P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+P361+P353, P308+P313, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methylcyclopentadiene is any of three isomeric cyclic dialkenes with the formula C5MeH5 (Me = CH3). These isomers are the organic precursor to the methylcyclopentadienyl ligand (C5H4Me, often denoted as Cp′), commonly found in organometallic chemistry.

As with cyclopentadiene, methylcyclopentadiene is prepared by thermal cracking of its Diels–Alder dimer, followed by distillation for removal of cyclopentadiene, a common impurity.[1]

  1. ^ Darkwa, James; Giolando, Dean M.; Murphy, Catherine Jones; Rauchfuss, Thomas B. (1990). "Bis(η5-Methylcyclopentadienyl)Titanium Pentasulfide, Bis(η-Methylcyclopentadienyl)-Divanadium Pentasulfide, and Bis(η5-Methylcyclopentadienyl)Divanadium Tetrasulfide". Inorg. Synth. 27: 51. doi:10.1002/9780470132586.ch10.