40288

6,6-Dimethylfulvene

≥95%

• Synonyme(s) : 5-(1-Methylethylidene)-1,3-cyclopentadiene, 5-Isopropylidene-1,3-cyclopentadiene
• 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

Propriétés

• 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

Description

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.

Informations sur la sécurité

• Pictogrammes: 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