214027
1,2,3,4,5-Pentamethylcyclopentadiene
95%
Synonym(s):
1,2,3,4,5-Pentamethyl-1,3-cyclopentadiene
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About This Item
Empirical Formula (Hill Notation):
C10H16
CAS Number:
Molecular Weight:
136.23
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-743-4
Beilstein/REAXYS Number:
1849832
MDL number:
Assay:
95%
Quality Segment
assay
95%
refractive index
n
bp
58 °C/13 mmHg (lit.)
density
0.87 g/mL at 25 °C (lit.)
SMILES string
CC1C(C)=C(C)C(C)=C1C
InChI
1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3
InChI key
WQIQNKQYEUMPBM-UHFFFAOYSA-N
General description
Mechanism of the Diels-Alder reaction of paramagneticendohedral metallofullerene and 1,2,3,4,5-pentamethylcyclopentadiene has been studied. Three-step large-scale preparation of 1,2,3,4,5-pentamethylcyclopentadiene has been reported. Reaction of 1,2,3,4,5-pentamethylcyclopentadiene (HCp*) with actinide ions in gas phase has been investigated by laser ablation mass spectrometry. It undergoes radical cation catalyzed cycloaddition with electron rich allenes to form Diels-Alder product.
Application
1,2,3,4,5-pentamethylcyclopentadiene was used as:
- Growth modifier chemical, during metal organic chemical vapour deposition of iron from iron pentacarbonyl.
- Ligand in "one-pot" iridium-catalyzed transformation of alcohols to amides via the intermediacy of oximes.
- Raw material for the synthesis of [Cp*Rh(bpy)H2O]2+ (Cp* = pentamethylcyclopentadienyl, bpy = 2,2′-bipyridyl), an electron mediator in the regeneration process of NADH.
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