40288
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:
Molecular Weight:
106.17
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1616308
Assay:
≥95%
Form:
liquid
Quality Level
assay
≥95%
form
liquid
refractive index
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
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.
Disclaimer
Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.
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signalword
Danger
hcodes
Hazard Classifications
Asp. Tox. 1 - Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
109.4 °F - closed cup
flash_point_c
43 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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Cycloaddition of 6, 6-Dimethylfulvene with Benzynes1.
Muneyuki R and Tanida H.
The Journal of Organic Chemistry, 31(6), 1988-1990 (1966)
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 40288-5ML | 04061837323768 |