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1,2,3,4,5-Pentamethylcyclopentadiene

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1,2,3,4,5-Pentamethylcyclopentadiene Basic information

Product Name:
1,2,3,4,5-Pentamethylcyclopentadiene
Synonyms:
  • Cyclopentadiene, 1,2,3,4,5-pentamethyl-
  • 1,2,3,4,5-PENTAMETHYLCYCLOPENTADIENE
  • 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene
  • 1,2,3,4,5-Pentamethylcyclopentadiene, tech
  • 1,2,3,5,5-pentamethylcyclopenta-1,3-diene
  • PENTAMETHYLCYCLOPENTADIENE
  • 1,2,3,4,5-PENTAMETHYLCYCLOPENTADIENE, 95 %
  • PENTAMETHYLCYCLOPENTADIENE 98+%
CAS:
4045-44-7
MF:
C10H16
MW:
136.23
EINECS:
223-743-4
Product Categories:
  • organic compound
  • In organic synthesis, high-energy rocket fuel, plasticizer, surface coating, curing agent, polymer synthetic materials
  • Alkenes
  • Cyclic
  • Organic Building Blocks
Mol File:
4045-44-7.mol
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1,2,3,4,5-Pentamethylcyclopentadiene Chemical Properties

Boiling point:
58 °C13 mm Hg(lit.)
Density 
0.87 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.474(lit.)
Flash point:
112 °F
storage temp. 
Store below +30°C.
form 
Liquid
color 
Clear colorless to yellow-orange, may darken on storage
Specific Gravity
0.87
Water Solubility 
Miscible with methanol. dichloromethane and ethyl acetate. Slightly miscible with water.
Sensitive 
Light Sensitive
BRN 
1849832
Stability:
store cold
CAS DataBase Reference
4045-44-7(CAS DataBase Reference)
NIST Chemistry Reference
1,3-Cyclopentadiene, 1,2,3,4,5-pentamethyl-(4045-44-7)
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Safety Information

Risk Statements 
10
Safety Statements 
16
RIDADR 
UN 3295 3/PG 3
WGK Germany 
3
9-23
HazardClass 
3
PackingGroup 
III
HS Code 
29021990

MSDS

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1,2,3,4,5-Pentamethylcyclopentadiene Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid

Uses

1,2,3,4,5-Pentamethylcyclopentadiene serves as a precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl. It is used as a growth modifier chemical, during metal organic chemical vapor deposition of iron from iron pentacarbonyl. It is used as a ligand in "one-pot" iridium-catalyzed transformation of alcohols to amides. Further, it acts as an electron mediator in the regeneration process of nicotinamide adenine dinucleotide. In addition to this, it undergoes radical cation catalyzed cycloaddition reaction with allenes to get Diels-Alder product.

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.

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