217166
1-Methoxy-1,3-cyclohexadiene
technical grade, 65%
Synonym(s):
2,3-Dihydroanisole
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About This Item
Empirical Formula (Hill Notation):
C7H10O
CAS Number:
Molecular Weight:
110.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
218-483-3
MDL number:
InChI key
LNRUJSUKKBJFOM-UHFFFAOYSA-N
InChI
1S/C7H10O/c1-8-7-5-3-2-4-6-7/h2-3,5H,4,6H2,1H3
SMILES string
COC1=CC=CCC1
grade
technical grade
concentration
65%
refractive index
n20/D 1.488 (lit.)
bp
40 °C/15 mmHg (lit.)
density
0.929 g/mL at 25 °C (lit.)
General description
1-Methoxy-1,3-cyclohexadiene is a useful Diels-Alder diene employed in Diels-Alder cycloadditions. It undergoes Diels-Alder reaction with alkyne to yield anisole derivative.
Application
1-Methoxy-1,3-cyclohexadiene was used in the following studies:
- Synthesis of tetracyclic polyhydroxyquinones via Diels-Alder reaction.
- Synthesis of tetra-ortho-substituted biaryls via Diels-Alder reaction.
- Synthesis of optically active form of dihydroisocoumarin fragment of the gastroprotective natural product AI-77-B, via regiospecific Diels-Alder reaction with an acetylenic ester derivative.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
80.6 °F - closed cup
flash_point_c
27 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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Bradley O Ashburn et al.
Organic & biomolecular chemistry, 6(2), 255-257 (2008-01-05)
A series of nitrophenyl acetylenes were evaluated for their utility in a cycloaddition-cycloreversion approach to polysubstituted biaryls. ortho-Nitrophenyl acetylene consistently provided the target biaryls in superior yields as compared to the meta and para nitro substituted variants.
Bradley O Ashburn et al.
Journal of the American Chemical Society, 129(29), 9109-9116 (2007-07-03)
The application of the Diels-Alder approach to biaryls (DAB) is described for the synthesis of tetra-ortho-substituted biaryl compounds containing orthogonally functionalized substituents. The syntheses of phosphorus-containing, disubstituted alkynes and carbonyl-containing, disubstituted alkynes were accomplished in two to three steps from
M. Carmen Carreño et al.
The Journal of organic chemistry, 61(18), 6136-6138 (1996-09-06)
The synthesis of tetracyclic polyhydroxyquinones 5a and 5b was achieved through a sequence involving two Diels-Alder reactions with 1-methoxy-1,3-cyclohexadiene: the first with 2-(p-tolylthio)naphthazarin and the second on the resulting tricyclic derivative previously transformed into a (p-tolylsulfinyl)naphthazarin. The success of this
Stereoselective synthesis of dihydroisocoumarin moiety of microbial agent AI-77-B: a Diels-Alder based strategy.
Ghosh AK and Cappiello J.
Tetrahedron Letters, 39(48), 8803-8806 (1998)
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