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40288

6,6-Dimethylfulvene

≥95%

Synonym(s):

5-(1-Methylethylidene)-1,3-cyclopentadiene, 5-Isopropylidene-1,3-cyclopentadiene

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Pack SizeSKUAvailabilityPrice
5 mL
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$147.00

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

$147.00

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Quality Segment

100

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 undergoes nucleophilic reaction with lithium dichloromethide in the presence of THF at -75°C, selectively at its exocyclic double bond.
6,6-Dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene] is a nonaromatic carbocyclic analog of isopropylbenzene.[1] 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.[2] Metal-free hydrogenation of 6,6-dimethylfulvene via frustrated Lewis pair (FLP) mediated triple domino reaction has been reported.[3]The biotransformation of 6,6-dimethylfulvene by Pseudomonas putida RE213 has been studied.Cycloaddition of 6,6-dimethylfulvene with benzynes has been reported.

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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This Item
646369272205187437
6,6-Dimethylfulvene ≥95%

Sigma-Aldrich

40288

6,6-Dimethylfulvene

6,6-Dimethylfulvene technical grade

Sigma-Aldrich

646369

6,6-Dimethylfulvene

6-(Dimethylamino)fulvene 98%

Sigma-Aldrich

272205

6-(Dimethylamino)fulvene

Bis(trimethylsilyl)acetylene 99%

Sigma-Aldrich

187437

Bis(trimethylsilyl)acetylene

assay

≥95%

assay

-

assay

98%

assay

99%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

form

liquid

form

-

form

-

form

-

bp

76-77 °C/50 mmHg (lit.)

bp

76-77 °C/50 mmHg (lit.)

bp

-

bp

136-137 °C (lit.)

density

0.881 g/mL at 25 °C (lit.)

density

0.881 g/mL at 25 °C (lit.)

density

-

density

0.752 g/mL at 25 °C (lit.)

refractive index

n20/D 1.548

refractive index

n20/D 1.548 (lit.)

refractive index

-

refractive index

n20/D 1.427 (lit.)

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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

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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)
Sergej Tamke et al.
Organic & biomolecular chemistry, 12(45), 9139-9144 (2014-10-09)
The frustrated Lewis pair (FLP) mediated hydrosilylation of pentafulvenes is described yielding allyl silanes with high regioselectivity in excellent yields. While phenyl substituted allyl silanes undergo B(C6F5)3-mediated rearrangement to vinyl silanes, dimethyl derivatives experience FLP-catalyzed hydrogenation followed by an unprecedented
Michael H Howard et al.
The Journal of organic chemistry, 68(1), 120-129 (2003-01-08)
Reaction of 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene (BTF; 1) with 6,6-dimethylfulvene (2) affords the expected Diels-Alder cycloadduct, 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile (3), in good yield. The cycloadduct 3 is unstable and exists in equilibrium with the starting materials in less polar solvents. In more polar environment, the
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Global Trade Item Number

SKUGTIN
40288-5ML04061837323768

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