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217166

Sigma-Aldrich

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:
2161-90-2
Molecular Weight:
110.15
EC Number:
218-483-3
MDL number:
MFCD00001533
UNSPSC Code:
12352100
PubChem Substance ID:
24852997
NACRES:
NA.22

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.)

SMILES string

COC1=CC=CCC1

InChI

1S/C7H10O/c1-8-7-5-3-2-4-6-7/h2-3,5H,4,6H2,1H3

InChI key

LNRUJSUKKBJFOM-UHFFFAOYSA-N

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

80.6 °F - closed cup

Flash Point(C)

27 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
0000028246
0000033873
MKBD2736V
MKBD2736
16106TY

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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.
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)
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

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