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Merck

125415

Sigma-Aldrich

1,4-Cyclohexadien

97%

Synonym(e):

1,4-Dihydrobenzol

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About This Item

Empirische Formel (Hill-System):
C6H8
CAS-Nummer:
Molekulargewicht:
80.13
Beilstein:
1900733
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Assay

97%

Form

liquid

Enthält

~0.1% hydroquinone as stabilizer

Verunreinigungen

3% benzene

Brechungsindex

n20/D 1.472 (lit.)

bp

88-89 °C (lit.)

Dichte

0.847 g/mL at 25 °C (lit.)

Lagertemp.

2-8°C

SMILES String

C1C=CCC=C1

InChI

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

InChIKey

UVJHQYIOXKWHFD-UHFFFAOYSA-N

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Verwandte Kategorien

Allgemeine Beschreibung

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.

Anwendung

Useful for the reduction of radical intermediates formed in electron-transfer mediated ring-opening reactions
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.

Piktogramme

FlameHealth hazard

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Blood

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

19.4 °F - closed cup

Flammpunkt (°C)

-7 °C - closed cup


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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)
Organometallics, 25, 5456-5456 (2006)
Yide Gao et al.
The journal of physical chemistry. A, 113(25), 6955-6963 (2009-06-06)
A quantitative understanding of the thermochemistry of cyclohexadienyl radical and 1,4-cyclohexadiene is beneficial for diverse areas of chemistry. Given the interest in these two species, it is surprising that more detailed thermodynamic data concerning the homolytic C-H bond enthalpies of
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
Kazutada Ikeuchi et al.
Organic letters, 14(23), 6016-6019 (2012-11-15)
Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic

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