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214027 Sigma-Aldrich

1,2,3,4,5-Pentamethylcyclopentadiene

95%

  • CAS Number 4045-44-7

  • Empirical Formula (Hill Notation) C10H16

  • Molecular Weight 136.23

  •  Beilstein/REAXYS Number 1849832

  •  EC Number 223-743-4

  •  MDL number MFCD00001354

  •  PubChem Substance ID 24852821

  •  NACRES NA.22

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Properties

Related Categories Alkenes, Building Blocks, Chemical Synthesis, Cyclic, Organic Building Blocks More...
Quality Level   200
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

Description

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.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
RIDADR 
UN 3295C 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
111.2 °F - closed cup
Flash Point(C) 
44 °C - closed cup

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Protocols & Articles

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

Peer-Reviewed Papers
15

References

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