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136697

Sigma-Aldrich

Hexamethyldewarbenzene

97%

Synonym(s):

1,2,3,4,5,6-Hexamethylbicyclo[2.2.0]hexa-2,5-diene

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About This Item

Empirical Formula (Hill Notation):
C12H18
CAS Number:
7641-77-2
Molecular Weight:
162.27
EC Number:
231-576-3
MDL number:
MFCD00001337
UNSPSC Code:
12352100
PubChem Substance ID:
24848292

Assay

97%

form

liquid

refractive index

n20/D 1.448 (lit.)

bp

60 °C/20 mmHg (lit.)

mp

7 °C (lit.)

density

0.803 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1=C(C)C2(C)C(C)=C(C)C12C

InChI

1S/C12H18/c1-7-8(2)12(6)10(4)9(3)11(7,12)5/h1-6H3

InChI key

RVNQQZMIWZPGNA-UHFFFAOYSA-N

General description

Hexamethyl dewar benzene on 1,2-addition with transient W(CO)5-complexed phosphinidenes affords the novel 3-phosphatricyclo[3.2.0.0(2,4)]hept-6-ene complexes. It undergoes partial rearrangement to give hexamethylbenzene during its epoxidation using (tetraphenylporphyrinato)iron(III)chloride and m-chloroperbenzoic acid.

accessory

Product No.
Description
Pricing

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

95.0 °F - closed cup

Flash Point(C)

35 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Isomerization of hexamethyl (Dewar benzene) to hexamethylbenzene catalyzed by electron acceptors. Thermal generation of an exciplex.
Peacock NJ and Schuster GB.
Journal of the American Chemical Society, 105(11), 3632-3638 (1983)
Erik P A Couzijn et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(5), 1499-1507 (2007-11-23)
1,2-Addition of transient W(CO)(5)-complexed phosphinidenes exo to hexamethyl Dewar benzene affords the novel 3-phosphatricyclo[3.2.0.0(2,4)]hept-6-ene complexes. The fused tricyclic phosphiranes are obtained as both the Z and the thermally less stable E isomers, the (31)P NMR chemical shifts of which differ
Mechanisms of hemin-catalyzed epoxidations: electron transfer from alkenes.
Traylor TG and Miksztal AR.
Journal of the American Chemical Society, 109(9), 2770-2774 (1987)

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