1,3-CYCLOHEXADIENE

1,3-CYCLOHEXADIENE Basic information
Product Name:1,3-CYCLOHEXADIENE
Synonyms:1,3-CYCLOHEXADIENE;1,2-DIHYDROBENZENE;l,3-Cyclohexadiene;1,3-Cyclohexadiene (stabilized with BHT);1,3-Cyclohexadiene,96%;1,3-Cyclohexadiene, stabilized, 96%;1,3-Cyclohexadiene, 96%, stab.;1,3-Cyclohexadiene, 96%, stabilized
CAS:592-57-4
MF:C6H8
MW:80.13
EINECS:209-764-1
Product Categories:Miscellaneous Reagents;Miscellaneous
Mol File:592-57-4.mol
1,3-CYCLOHEXADIENE Structure
1,3-CYCLOHEXADIENE Chemical Properties
Melting point -98 °C
Boiling point 80 °C (lit.)
density 0.841 g/mL at 25 °C (lit.)
refractive index n20/D 1.474(lit.)
Fp −2 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form Liquid
color Clear colorless to light yellow
Water Solubility Slightly miscible with methanol. Immiscible with water.
BRN 506024
Stability:Light Sensitive
LogP2.470
CAS DataBase Reference592-57-4(CAS DataBase Reference)
EPA Substance Registry System1,3-Cyclohexadiene (592-57-4)
Safety Information
Hazard Codes F
Risk Statements 11-10-37
Safety Statements 9-16-29-33
RIDADR UN 3295 3/PG 2
WGK Germany 3
RTECS GU4702350
9
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29021990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
1,3-CYCLOHEXADIENE Usage And Synthesis
Chemical Propertiesclear colorless to light yellow liquid
Uses1,3-Cyclohexadiene can undergo:
  • C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products.
  • Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.
  • Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.
  • Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.

Uses1,3-Cyclohexadiene is used as a hydrogen donor in transfer hydrogenation. It is used in the conversion to benzene. It is useful in the study of proteomics research.
Uses1,3-Cyclohexadiene can undergo:
C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products.
Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.
Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.
Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.



Preparation1,3-Cyclohexadiene has been prepared by dehydration of cyclohexen-3-ol, by pyrolysis at 540° of the diacetate of cyclohexane-1,2-diol, by dehydrobromination with quinoline of 3-bromocyclohexene, by treating the ethyl ether of cyclohexen-3-ol with potassium bisulfate, by heating cyclohexene oxide with phthalic anhydride, by treating cyclohexane-1,2-diol with concentrated sulfuric acid, by treatment of 1,2-dibromocyclohexane with tributylamine, with sodium hydroxide in ethylene glycol, and with quinoline, and by treatment of 3,6-dibromo-cyclohexene with sodium.
1 3-cyclohexadiene synthesis
DefinitionChEBI: Cyclohexa-1,3-diene is a cyclohexadiene.
Purification MethodsDistil the diene from NaBH4 or Na under N2 and collect it in a trap cooled in Dry Ice. It is highly flammable. [Marvel & Martell, J Am Chem Soc 81 450 1959, Beilstein 5 IV 382.]
METHYL CYCLOHEXADIENE CHORISMIC ACID BARIUM SALT CIS-1,2-DIHYDROCATECHOL 7-DEHYDROCHOLESTERYL BENZOATE 1-METHOXY-1,3-CYCLOHEXADIENE O-BROMANIL GLIOTOXIN TRICARBONYL(2-METHOXYCYCLOHEXADIENYLIUM)IRON HEXAFLUOROPHOSPHATE DIMETHYL 1,3-CYCLOHEXADIENE-1,4-DICARBOX YLATE, TECH., 90 1,2-dihydro-3,4,5,6-tetraphenylphthalic anhydride 3-AMINO-2,3-DIHYDROBENZOIC ACID HYDROCHLORIDE ADRENOCHROME Ergosterol sodium 5-[(aminocarbonyl)hydrazono]-2,3,5,6-tetrahydro-1-methyl-6-oxo-1H-indole-3-sulphonate (-)-P-MENTHA-1,5-DIENE CIS-(1S,2R)-3-METHYL-3,5-CYCLOHEXADIENE-1,2- DIOL 4,5-DIMETHOXY-1,2-BENZOQUINONE 7-DEHYDROCHOLESTEROL ACETATE

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