125415
1,4-Cyclohexadiene
97%
Synonym(s):
1,4-Dihydrobenzene
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5 ML
$72.30
25 ML
$176.00
100 ML
$456.00
About This Item
Empirical Formula (Hill Notation):
C6H8
CAS Number:
Molecular Weight:
80.13
Beilstein/REAXYS Number:
1900733
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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[1]. It can rapidly replace benzyl groups of N-benzyloxycarbamates, benzyl esters, benzyl ethers and benzyl amines with hydrogen[1]. It forms benzene at elevated temperatures in the presence of a ruthenium(II)-triphenylphosphine catalyst[2].
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[3].
Useful for the reduction of radical intermediates formed in electron-transfer mediated ring-opening reactions
signalword
Danger
hcodes
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
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A key factor in parent and fragment ion formation on irradiation with an intense femtosecond laser pulse.
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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
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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
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
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