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125415

Sigma-Aldrich

1,4-Cyclohexadiene

97%

Sinónimos:

1,4-Dihydrobenzene

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About This Item

Fórmula empírica (notación de Hill):
C6H8
Número de CAS:
628-41-1
Peso molecular:
80.13
Beilstein/REAXYS Number:
1900733
MDL number:
MFCD00001535
UNSPSC Code:
12352100
PubChem Substance ID:
24847665
NACRES:
NA.22

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
GHS02,GHS08

signalword

Danger

Hazard Classifications

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

target_organs

Blood

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

19.4 °F - closed cup

flash_point_c

-7 °C - closed cup

Certificados de análisis (COA)

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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)
Organometallics, 25, 5456-5456 (2006)
Kyung-Bin Cho et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(33), 10444-10453 (2012-06-21)
The experimentally measured bimolecular reaction rate constant, k(2), should in principle correlate with the theoretically calculated rate-limiting free energy barrier, ΔG(≠), through the Eyring equation, but it fails quite often to do so due to the inability of current computational
Jaya S Kudavalli et al.
Organic letters, 12(23), 5550-5553 (2010-11-09)
Benzene-cis- and trans-1,2-dihydrodiols undergo acid-catalyzed dehydration at remarkably different rates: k(cis)/k(trans) = 4500. This is explained by formation of a β-hydroxycarbocation intermediate in different initial conformations, one of which is stabilized by hyperconjugation amplified by an aromatic no-bond resonance structure
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