40288

6,6-Dimethylfulvene

≥95%

• Sinónimos: 5-(1-Methylethylidene)-1,3-cyclopentadiene, 5-Isopropylidene-1,3-cyclopentadiene
• Fórmula empírica (notación de Hill): C₈H₁₀
• Número de CAS: 2175-91-9
• Peso molecular: 106.17
• Beilstein: 1616308
• Número MDL: MFCD00011655
• Código UNSPSC: 12352100
• ID de la sustancia en PubChem: 57649965
• NACRES: NA.22

Propiedades

• Nivel de calidad: 100
• Ensayo: ≥95%
• Formulario: liquid
• índice de refracción: n20/D 1.548 (lit.); n20/D 1.548
• bp: 76-77 °C/50 mmHg (lit.)
• densidad: 0.881 g/mL at 25 °C (lit.)
• temp. de almacenamiento: −20°C
• cadena SMILES: C\C(C)=C1/C=CC=C1
• InChI: 1S/C8H10/c1-7(2)8-5-3-4-6-8/h3-6H,1-2H3
• Clave InChI: WXACXMWYHXOSIX-UHFFFAOYSA-N

Descripción

Descripción general

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.

Aplicación

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.

Información de seguridad

• Pictogramas: GHS02,GHS08
• Palabra de señalización: Danger
• Frases de peligro: H226,H304
• Consejos de prudencia: P210 - P233 - P240 - P241 - P301 + P310 - P331
• Clasificaciones de peligro: Asp. Tox. 1 - Flam. Liq. 3
• Código de clase de almacenamiento: 3 - Flammable liquids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): 109.4 °F - closed cup
• Punto de inflamabilidad (°C): 43 °C - closed cup
• Equipo de protección personal: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter