40288
6,6-Dimethylfulvene
≥95%
Synonym(s):
5-(1-Methylethylidene)-1,3-cyclopentadiene, 5-Isopropylidene-1,3-cyclopentadiene
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About This Item
Empirical Formula (Hill Notation):
C8H10
CAS Number:
Molecular Weight:
106.17
Beilstein:
1616308
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥95%
form
liquid
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
SMILES string
C\C(C)=C1/C=CC=C1
InChI
1S/C8H10/c1-7(2)8-5-3-4-6-8/h3-6H,1-2H3
InChI key
WXACXMWYHXOSIX-UHFFFAOYSA-N
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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.
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Asp. Tox. 1 - Flam. Liq. 3
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
109.4 °F - closed cup
Flash Point(C)
43 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Cycloaddition of 6, 6-Dimethylfulvene with Benzynes1.
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Recknagel A and Edelmann FT.
Angewandte Chemie (International Edition in English), 30(6), 693-694 (1991)
Carbenic philicity: 6, 6-dimethylfulvene as an indicator substrate.
Moss RA, et al.
Journal of the American College of Cardiology, 103(9), 2413-2415 (1981)
The Diels-Alder Reaction and the Rearrangement of the Maleic Anhydride Adducts of 6, 6-Dimethylfulvene.
Craig D, et al.
Journal of the American Chemical Society, 76(18), 4573-4575 (1954)
Sergej Tamke et al.
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The frustrated Lewis pair (FLP) mediated hydrosilylation of pentafulvenes is described yielding allyl silanes with high regioselectivity in excellent yields. While phenyl substituted allyl silanes undergo B(C6F5)3-mediated rearrangement to vinyl silanes, dimethyl derivatives experience FLP-catalyzed hydrogenation followed by an unprecedented
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