125415
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1900733
Product Name
1,4-Cyclohexadiene, 97%
InChI
1S/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2
SMILES string
C1C=CCC=C1
InChI key
UVJHQYIOXKWHFD-UHFFFAOYSA-N
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
Quality Level
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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
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.
signalword
Danger
hcodes
Hazard Classifications
Carc. 1A - Flam. Liq. 2 - Muta. 1B - STOT RE 2
target_organs
Blood
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
19.4 °F - closed cup
flash_point_c
-7 °C - closed cup
Regulatory Information
危险化学品
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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)
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
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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