40288

6,6-Dimethylfulvene

≥95%

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

Properties

• 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

Description

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.

Safety Information

• Pictograms: 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