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6,6-Dimethylfulvene

ALDRICH/40288 - ≥95%

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
MDL Number: MFCD00011655
Linear Formula: C8H10
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-40288-5ML 5 mL
 $138.00
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assay ≥95%
bp 76-77 °C/50 mmHg (lit.)
density 0.881 g/mL at 25 °C (lit.)
form liquid
InChI 1S/C8H10/c1-7(2)8-5-3-4-6-8/h3-6H,1-2H3
InChI key WXACXMWYHXOSIX-UHFFFAOYSA-N
Quality Level 100 
refractive index n20/D 1.548
  n20/D 1.548 (lit.)
SMILES string CC(C)=C1/C=CC=C1
storage temp. −20°C
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 undergoes nucleophilic reaction with lithium dichloromethide in the presence of THF at -75°C, selectively at its exocyclic double bond.
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.
Packaging: 5 mL in glass bottle
Symbol GHS02GHS08  GHS02,GHS08
Signal word Danger
Hazard statements H226 - H304
Precautionary statements P210 - P301 + P310 + P331
Hazard Codes Xn
Risk Statements 10-65
Safety Statements 16-62
RIDADR UN 3295C 3 / PGIII
WGK Germany WGK 3
Flash Point(F) 109.4 °F - closed cup
Flash Point(C) 43 °C - closed cup
Purity ≥95%
bp 76-77 °C/50 mmHg (lit.)
Density 0.881 g/mL at 25 °C (lit.)
Refractive Index n20/D 1.548 (lit.); n20/D 1.548
Storage Temp. −20°C
UNSPSC 12352100

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