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40288

Sigma-Aldrich

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:
2175-91-9
Molecular Weight:
106.17
Beilstein:
1616308
MDL number:
MFCD00011655
UNSPSC Code:
12352100
PubChem Substance ID:
57649965
NACRES:
NA.22

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.

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H226,H304

Precautionary Statements

P210 - P301 + P310 + P331

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Cycloaddition of 6, 6-Dimethylfulvene with Benzynes1.
Muneyuki R and Tanida H.
The Journal of Organic Chemistry, 31(6), 1988-1990 (1966)
One-Step Synthesis of Organolanthanide (II) Complexes from the Metal.
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)
Sergej Tamke et al.
Organic & biomolecular chemistry, 12(45), 9139-9144 (2014-10-09)
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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