Methylcyclopentadiene

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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).
checkY verify (what is checkY☒N ?)

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

Diels–Alder dimer, followed by distillation for removal of cyclopentadiene, a common impurity.[1]

Methylcyclopentadienyl anion

diastereotopic
ring protons.

Deprotonation of methylcyclopentadiene gives the

organic solvents
.

Cp′ can be used to probe the structure of organometallic complexes. For example, Cp′Fe(PPh3)(CO)I has four different signals in the

diastereotopic relationship as a result of being part of a chiral complex. The achiral precursor complex Cp′Fe(CO)2I has only two signals for those hydrogens and three for those carbons, indicating a symmetric structure.[3]

References

  1. doi:10.1002/9780470132586.ch10
    .
  2. doi:10.15227/orgsyn.036.0031
    .
  3. doi:10.1016/S0022-328X(00)99395-1
    .

See also
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