Saltar al contenido
MilliporeSigma
Todas las fotos(1)

Key Documents

View All Documentation

40288

Sigma-Aldrich

6,6-Dimethylfulvene

≥95%

Sinónimos:

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

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(1)

About This Item

Fórmula empírica (notación de Hill):
C8H10
Número de CAS:
2175-91-9
Peso molecular:
106.17
Beilstein/REAXYS Number:
1616308
MDL number:
MFCD00011655
UNSPSC Code:
12352100
PubChem Substance ID:
57649965
NACRES:
NA.22

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

¿Está buscando productos similares? Visita Guía de comparación de productos

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_germany

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

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
BCCD0490
BCCB2529
BCBX0185
BCBW0863
BCBT6997

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Los clientes también vieron

Slide 1 of 4

1 of 4

Propylene ≥99%

Sigma-Aldrich

295663

Propylene

4-Iodobenzoic acid 98%

Sigma-Aldrich

206547

4-Iodobenzoic acid

Methyl 4-iodobenzoate 97%

Sigma-Aldrich

679100

Methyl 4-iodobenzoate

Methyllithium solution 1.6 M in diethyl ether

Sigma-Aldrich

197343

Methyllithium solution

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)
Functionalization of 6, 6-Dimethylfulvene: A Fulvene Analogue of the Aldol Condensation.
Nystrom JE, et al.
Tetrahedron Letters, 29(39), 4997-5000 (1988)
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
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
R W Eaton et al.
Applied and environmental microbiology, 62(3), 756-760 (1996-03-01)
The biotransformation of 6,6-dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene], a nonaromatic C(inf5) carbocyclic analog of isopropylbenzene, was examined by using Pseudomonas putida RE213, a Tn5-generated dihydrodiol-accumulating mutant of the isopropylbenzene-degrading strain P. putida RE204. 6,6-Dimethylfulvene was converted to a single chiral product identified as
Ver todos los artículos relacionados

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico