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 Level
assay
95%
refractive index
n20/D 1.474 (lit.)
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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Articles
The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.
An improved synthesis of 1,2,3,4,5-pentamethylcyclopentadiene.
Kohl FX and Jutzi P.
Journal of Organometallic Chemistry, 243(1), 119-121 (1983)
Nathan A Owston et al.
Organic letters, 9(1), 73-75 (2006-12-29)
[reaction: see text] The iridium catalyst [Ir(Cp*)Cl2]2 is effective for the rearrangement of oximes to furnish amides. The reaction has been combined with catalytic transfer hydrogenation between an alcohol and alkene to allow the conversion of alcohols into amides in
Journal of Organometallic Chemistry, 472, 359-359 (1994)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 214027-5G | 04061838773098 |
| 214027-25G | 04061838773081 |