7318-67-4

Basic information

• Product Name: CIS-1,4-HEXADIENE
• Synonyms: CIS-1,4-HEXADIENE;(4Z)-1,4-Hexadiene;(z)-1,4-hexadiene;(z)-4-hexadiene;(Z)-CH2=CHCH2CH=CHCH3;1,4-cis-hexadiene;1,4-hexadiene-cis;1,cis-4-hexadiene
• CAS NO: 7318-67-4
• Molecular Formula: C₆H₁₀
• Molecular Weight: 82.14
• EINECS: 230-783-6
• Product Categories: Acyclic;Alkenes;Organic Building Blocks
• Mol File: 7318-67-4.mol

Chemical Properties

• Melting Point: -94.9°C (estimate)
• Boiling Point: 65-66 °C(lit.)
• Flash Point: -46 °C
• Appearance: /
• Density: 0.707 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.415
• BRN: 1839519
• CAS DataBase Reference: CIS-1,4-HEXADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,4-HEXADIENE(7318-67-4)
• EPA Substance Registry System: CIS-1,4-HEXADIENE(7318-67-4)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-65
• Safety Statements: 16-62
• RIDADR: UN 2458 3/PG 2
• WGK Germany: 3
• RTECS: MM1997000
• Hazardous Substances Data: 7318-67-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
CIS-1,4-HEXADIENE is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to undergo reactions such as rearrangement and complex formation, making it a valuable building block in the production of other chemicals.
Used in the Production of Complexes:
CIS-1,4-HEXADIENE is used as a precursor in the formation of metal complexes, such as the trans-1,3-hexadiene-iron tricarbonyl complex (I) and the trans,trans-2,4-hexadiene complex (II). These complexes have potential applications in various fields, including catalysis and materials science.
Used in Research and Development:
The study of the mechanism of conversion of CIS-1,4-HEXADIENE to trans-2-methyl-1,3-pentadiene in the presence of a nickel catalyst provides valuable insights into the behavior of hydrocarbons and their transformations. This knowledge can be applied to develop new synthetic routes and improve existing processes in the chemical industry.

InChI:InChI=1/C6H10/c1-3-5-6-4-2/h3-4,6H,1,5H2,2H3/b6-4-

Upstream product

• 592-42-7 1,5-Hexadien 
• 79345-10-1 exo-2-methylbicyclo<3.1.0>hexan-3-one 
• 79345-10-1 endo-2-methylbicyclo<3.1.0>hexan-3-one 
• 74-85-1 ethene 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 78426-34-3 (Z)-5-methylenehept-2-ene 
• 78426-35-4 di(n-1-hexenyl)aluminum chloride 
• 592-46-1 hexa-2,4-diene 
• 592-41-6 1-hexene 
• 7642-09-3 cis-3-hexene 
• 13269-52-8 trans-3-Hexene 
• 4050-45-7 trans-2-hexene 
• 110-54-3 hexane 
• 928-91-6 (Z)-4-hexenol 
• 928-92-7 (E)-hex-4-en-1-ol 
• 592-42-7 1,5-Hexadien 
• 5194-51-4 (2E,4E)-hexa-2,4-diene 
• 5194-50-3 (E,Z)-2,4-hexadiene 
• 592-48-3 hexa-1,3-diene 

Relevant articles and documents

Selective [1,4]-Hydrovinylation of 1,3-Dienes with Unactivated Olefins Enabled by Iron Diimine Catalysts

The selective, intermolecular [1,4]-hydrovinylation of conjugated dienes with unactivated α-olefins catalyzed by α-diimine iron complexes is described. Value-added "skipped" diene products were obtained with exclusive [1,4]-selectivity, and the formation

KINETICS OF 1,5-HEXADIENE HYDROGENATION AND ISOMERIZATION ON A CHROMIUM CATALYST

The kinetics of the title reactions was studied in the presence of a catalyst obtained by thermal decomposition of tris(η3-2-propenyl)chromium.The catalyst proved to be active for hydrogenation at 298 K and under 92 kPa H2 but poor for migration of C=C bonds (studied at 333 K).Both the double bonds of the diene may undergo the transformation simultaneously in both the cases studied.Diethyl ether favors deactivation of the hydrogenation catalyst and moderates the isomerization reaction.The kinetic equations for the reactions studied are given.

Solution-Phase Photodecarbonylation of the Bicyclohexan-3-one System

Direct irradiation of solutions containing (-)-thujone (6) or (+)-isothujone (7) affords trans- and cis-5-methylene-6-methylhept-2-ene (8 and 9) in quantitative yield.The epimeric ketones give identical produc mixtures, which are somewhat temperature dependent.The product ratio remains constant throughout irradiation, and appropriate control experiments indicate that the observed diene mixture does not represent a rapidly established photostationary state.Limited epimerization of the ketones is observed although this process is much less efficient than extrusion of carbon monoxide.Quenching studies employing piperylene indicate that the majority of the decarbonylation products originate from a short-lived triplet state.Direct irradiation of solutions containing exo- or endo-2-methylbicyclohexan-3-one (10 or 11) yields trans- and cis-hexa-1,4-diene (12 and 13) in high yield.Again the epimeric ketones give identical product mixtures, which are slightly temperature dependent.Direct irradiation of solutions containing exo,exo-, exo,endo-, or endo,endo-2,4-dimethylbicyclohexan-3-one (16, 15, or 14) affords similar, but not identical, mixtures of trans,trans-, trans,cis-, and cis,cis-hepta-2,5-diene (17, 18, and 19) in high yield.Each of these product ratios is somewhat temparature dependent.These data are explained in terms of a mechanism involving biradical intermediates.Excitation followed by intersystem crossing leads to a short-lived triplet state which undergoes Norrish I cleavage toward the more substituted α position.The diene products are formed upon synchronous cleavage of the cyclopropane bond and loss of carbon monoxide.If internal rotation in the intermediate is rapid with respect to decay, the observed product ratios may be rationalized.Inefficient reclusure of the biradical species leads to limited epimerization of the bicyclohexan-3-ones.