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40288

Sigma-Aldrich

6,6-Dimethylfulvene

≥95%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C8H10
Numéro CAS:
2175-91-9
Poids moléculaire :
106.17
Numéro Beilstein :
1616308
Numéro MDL:
MFCD00011655
Code UNSPSC :
12352100
ID de substance PubChem :
57649965
Nomenclature NACRES :
NA.22

Pureté

≥95%

Forme

liquid

Indice de réfraction

n20/D 1.548 (lit.)
n20/D 1.548

Point d'ébullition

76-77 °C/50 mmHg (lit.)

Densité

0.881 g/mL at 25 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

C\C(C)=C1/C=CC=C1

InChI

1S/C8H10/c1-7(2)8-5-3-4-6-8/h3-6H,1-2H3

Clé InChI

WXACXMWYHXOSIX-UHFFFAOYSA-N

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Description générale

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.

Pictogrammes

FlameHealth hazard
GHS02,GHS08

Mention d'avertissement

Danger

Mentions de danger

H226,H304

Conseils de prudence

P210 - P301 + P310 + P331

Classification des risques

Asp. Tox. 1 - Flam. Liq. 3

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

109.4 °F - closed cup

Point d'éclair (°C)

43 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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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)
Functionalization of 6, 6-Dimethylfulvene: A Fulvene Analogue of the Aldol Condensation.
Nystrom JE, et al.
Tetrahedron Letters, 29(39), 4997-5000 (1988)
Michael H Howard et al.
The Journal of organic chemistry, 68(1), 120-129 (2003-01-08)
Reaction of 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene (BTF; 1) with 6,6-dimethylfulvene (2) affords the expected Diels-Alder cycloadduct, 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile (3), in good yield. The cycloadduct 3 is unstable and exists in equilibrium with the starting materials in less polar solvents. In more polar environment, the
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
R W Eaton et al.
Applied and environmental microbiology, 62(3), 756-760 (1996-03-01)
The biotransformation of 6,6-dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene], a nonaromatic C(inf5) carbocyclic analog of isopropylbenzene, was examined by using Pseudomonas putida RE213, a Tn5-generated dihydrodiol-accumulating mutant of the isopropylbenzene-degrading strain P. putida RE204. 6,6-Dimethylfulvene was converted to a single chiral product identified as
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