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40288 Aldrich

6,6-Dimethylfulvene

96%

Synonym: 5-(1-Methylethylidene)-1,3-cyclopentadiene, 5-Isopropylidene-1,3-cyclopentadiene

  • CAS Number 2175-91-9

  • Empirical Formula (Hill Notation) C8H10

  • Molecular Weight 106.17

  •  Beilstein Registry Number 1616308

  •  MDL number MFCD00011655

  •  PubChem Substance ID 57649965

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Properties

Related Categories Acyclic, Alkenes, Building Blocks, Chemical Synthesis, Organic Building Blocks More...
InChI Key   WXACXMWYHXOSIX-UHFFFAOYSA-N
assay   96%
refractive index   n20/D 1.548(lit.)
  n20/D 1.548
bp   76-77 °C/50 mmHg(lit.)
density   0.881 g/mL at 25 °C(lit.)
storage temp.   −20°C

Description

Packaging

5 mL in glass bottle

Application

6,6-Dimethylfulvene may be employed in the following studies:
• One-pot synthesis of ansa-metallocenes.
• Synthesis of endo and exo-adducts with maleic anhydride.
• Synthesis of fulvenols or the corresponding trimethylsilyl ethers.

General description

6,6-Dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene] is a nonaromatic carbocyclic analog of isopropylbenzene. 6,6-Dimethylfulvene reacts with 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene (BTF; 1) to afford the expected Diels-Alder cycloadduct, 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile. Metal-free hydrogenation of 6,6-dimethylfulvene via frustrated Lewis pair (FLP) mediated triple domino reaction has been reported.The biotransformation of 6,6-dimethylfulvene by Pseudomonas putida RE213 has been studied.Cycloaddition of 6,6-dimethylfulvene with benzynes has been reported.

6,6-Dimethylfulvene undergoes nucleophilic reaction with lithium dichloromethide in the presence of THF at -75°C, selectively at its exocyclic double bond.

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3295C 3 / PGIII
WGK Germany 
3
Flash Point(F) 
109.4 °F
Flash Point(C) 
43 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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