136697
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:
Molecular Weight:
162.27
UNSPSC Code:
12352100
PubChem Substance ID:
EC Number:
231-576-3
MDL number:
InChI key
RVNQQZMIWZPGNA-UHFFFAOYSA-N
InChI
1S/C12H18/c1-7-8(2)12(6)10(4)9(3)11(7,12)5/h1-6H3
SMILES string
CC1=C(C)C2(C)C(C)=C(C)C12C
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
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.
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
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
Regulatory Information
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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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