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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

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

95.0 °F - closed cup

flash_point_c

35 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
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)
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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