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Merck
CN

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:
2175-91-9
Molecular Weight:
106.17
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57649965
MDL number:
MFCD00011655
Beilstein/REAXYS Number:
1616308
Assay:
≥95%
Form:
liquid

Key Documents

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InChI

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

SMILES string

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

InChI key

WXACXMWYHXOSIX-UHFFFAOYSA-N

assay

≥95%

form

liquid

Quality Level

100

bp

76-77 °C/50 mmHg (lit.)

density

0.881 g/mL at 25 °C (lit.)

storage temp.

−20°C

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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.

pictograms

FlameHealth hazard
GHS02,GHS08

signalword

Danger

hcodes

H226,H304

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4523
BCCK6719
BCCD0490
BCCB2529
BCBX0185

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The Diels-Alder Reaction and the Rearrangement of the Maleic Anhydride Adducts of 6, 6-Dimethylfulvene.
Craig D, et al.
Journal of the American Chemical Society, 76(18), 4573-4575 (1954)
Cycloaddition of 6, 6-Dimethylfulvene with Benzynes1.
Muneyuki R and Tanida H.
The Journal of Organic Chemistry, 31(6), 1988-1990 (1966)
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)
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)
Functionalization of 6, 6-Dimethylfulvene: A Fulvene Analogue of the Aldol Condensation.
Nystrom JE, et al.
Tetrahedron Letters, 29(39), 4997-5000 (1988)
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