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125415

Sigma-Aldrich

1,4-Cyclohexadiene

97%

Synonym(s):

1,4-Dihydrobenzene

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About This Item

Empirical Formula (Hill Notation):
C6H8
CAS Number:
Molecular Weight:
80.13
Beilstein:
1900733
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

contains

~0.1% hydroquinone as stabilizer

impurities

3% benzene

refractive index

n20/D 1.472 (lit.)

bp

88-89 °C (lit.)

density

0.847 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C1C=CCC=C1

InChI

1S/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2

InChI key

UVJHQYIOXKWHFD-UHFFFAOYSA-N

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General description

1,4-Cyclohexadiene is an effective hydrogen donor for catalytic hydrogenation reactions. It can rapidly replace benzyl groups of N-benzyloxycarbamates, benzyl esters, benzyl ethers and benzyl amines with hydrogen. It forms benzene at elevated temperatures in the presence of a ruthenium(II)-triphenylphosphine catalyst.

Application

1,4-Cyclohexadiene (1,4-CHD) was used to study the formation of parent ion from heavy fragmentation of 1,4-CHD on irradiation with a high-intensity laser pulse.
Useful for the reduction of radical intermediates formed in electron-transfer mediated ring-opening reactions

Pictograms

FlameHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Carc. 1A - Flam. Liq. 2 - Muta. 1B - STOT RE 2

Target Organs

Blood

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

19.4 °F - closed cup

Flash Point(C)

-7 °C - closed cup


Certificates of Analysis (COA)

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Organometallics, 25, 5456-5456 (2006)
A key factor in parent and fragment ion formation on irradiation with an intense femtosecond laser pulse.
Harada H, et al.
Chemical Physics Letters, 342(5), 563-570 (2001)
Rapid removal of protecting groups from peptides by catalytic transfer hydrogenation with 1, 4-cyclohexadiene.
Felix AM,et al.
The Journal of Organic Chemistry, 43(21), 4194-4196 (1978)
Monika Ali Khan et al.
Chemical communications (Cambridge, England), 47(1), 215-217 (2010-08-24)
A cyclohexadiene ligand prepared by microbial arene 1,2-dihydroxylation undergoes spontaneous rearrangement upon complexation to tricarbonyliron(0). Subsequent iron removal affords a novel route to formal arene 2,3-dihydroxylation products enantiomeric to those obtainable by direct microbial arene oxidation.
William A Donald et al.
Dalton transactions (Cambridge, England : 2003), 41(11), 3185-3193 (2012-01-31)
Relatively little is known about structural transformations of very small metal clusters that result from the adsorption of molecules. Here, the ligand-induced structural transformation of Ag(5)(+)(g) by 1,4-cyclohexadiene, which is capable of binding metal clusters as a bidentate ligand, is

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