Skip to Content
Merck
CN

40288

6,6-Dimethylfulvene

≥95%

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCM4523
BCCK6719
BCCD0490
BCCB2529
BCBX0185

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Functionalization of 6, 6-Dimethylfulvene: A Fulvene Analogue of the Aldol Condensation.
Nystrom JE, et al.
Tetrahedron Letters, 29(39), 4997-5000 (1988)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service