930-65-4

Usage

Uses

Used in Chemical Synthesis:
4-Chlorocyclohexene is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity allows it to undergo various chemical reactions, making it a valuable building block in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-chlorocyclohexene is used as a key intermediate in the synthesis of various drug molecules. Its unique structure and reactivity enable the development of new drugs with improved therapeutic properties and reduced side effects.
Used in Agrochemical Industry:
4-Chlorocyclohexene is also used in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its ability to form stable and effective compounds makes it a valuable component in the development of new and improved agrochemical products.
Used in the Synthesis of Bicyclo[3.1.0]hexane Rings:
4-Chlorocyclohexene is used as a starting material for the creation of bicyclo[3.1.0]hexane rings via zirconium y-elimination. This reaction is an important method for the synthesis of complex organic molecules, particularly in the field of organic chemistry and materials science. The resulting bicyclo[3.1.0]hexane rings can be further modified and used in various applications, such as in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 7978, 1985 DOI: 10.1021/ja00312a030

InChI:InChI=1/C6H9Cl/c7-6-4-2-1-3-5-6/h1-2,6H,3-5H2

Upstream product

• 120-18-3 naphthalene-2-sulfonate 
• 30485-71-3 4-chlorocyclohexanol 
• 29538-77-0 trans-4-hydroxycyclohexyl chloride 
• 186-04-9 bicyclo[2.2.0]hexane 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 932-67-2 cyclohex-3-enecarbonyl chloride 
• 556-48-9 1,4-Cyclohexanediol 
• 100-50-5 3-Cyclohexene-1-carboxaldehyde 
• 110-83-8 cyclohexene 

Relevant academic research and scientific papers

Factors Influencing Conformational Preferences in Cyclohexenes

Conformational preferences have been measured for the first time for 4-substituted cyclohexenes in a solvent of low polarity.Measurements were made for the substituents Cl, Br, I, OH, OSiMe3, and CN and were compared with conformational preferences in cyclohexyl and exo-methylenecyclohex-3-yl.In the nearly nonpolar solvent CF2Cl2, in which intramolecular interactions are maximized, there is a much larger axial population for cyclohexen-4-yl than in cyclohexyl or exo-methylenecyclohex-3-yl.In particular, the dipolar interaction of the endocyclic double bond is reduced from that of the exocyclic double bond.This observation is confirmed by the almost negligible effect of symmetrizing the endocyclic double bond through 1,2-dimethyl substitution, in contrast with the large effect of symmetrizing the exocyclic double bond through 7,7-dimethyl substitution.Polar solvents increase the proportion of the axial conformer to a smaller extent for the endocyclic than for the exocyclic system, again in agreement with a lower dipolar effect in the endocyclic case.These results emphasize the anisotropic nature of the steric effects of double bonds.

MECHANISMS OF EPOXIDATIONS AND CHLORINATIONS OF HYDROCARBONS BY INORGANIC HYPOCHLORITE IN THE PRESENCE OF A PHASE-TRANSFER CATALYST.

Inorganic hypochlorite in the presence of a quarternary ammonium salt (phase-transfer catalyst) not only epoxidizes several arenes to arene oxides in high yields but also converts toluene to alpha -chlorotoluene, anisole to ring chlorinated anisoles, and alkenes to a complex mixture of chlorinated and oxidized products, including the epoxide. More detailed studies with this system indicate the following: (1) the high-yield conversion of toluenes to benzyl chlorides proceeds with a deuterium isotope effect of 3. 6 and a rho ** plus value of minus 1. 7: (2) p-chloroanisole is the major product from anisole and is formed in a 22-fold greater quantity than o-chloroanisole; (3) the epoxidation of cis- and trans-alkenes is stereoselective but not completely stereospecific; (4) the chlorination of saturated hydrocarbons occurs with a selectivity that is experimentally identical with that of chlorine monoxide.

The photochemical addition of N-haloamides to olefins: the influence of various factors on the competition between 1,2-addition and hydrogen abstraction

In the photodecomposition of N-haloamides (ZCONRX) in the presence of olefins, the 1,2-addition chain competes with the hydrogen abstraction chain(s) leading to the parent amide (the quantum yields for these processes are greater than unity).The following factors were shown to have an influence on this competition as measured by the yield of 1,2-addition and the yield of parent amide in methylene chloride solutions: (i) the N-halogen (higher yields of addition with X=Cl than with X=Br); (ii) the electronegativity of Z (increase of the yield of addition as the electronegativity of Z increases); (iii) the temperature (higher yields of addition at lower temperatures, and at -70 degC, better yields of addition (>90percent, R=H) for X=Br than for X=Cl); and (iv) the size of R (dramatic decrease of the yield of 1,2-addition in going from R=H to R=CH3).Surprisingly, the presence of a scavenger for HX had no influence on the yield of 1,2-addition.Both the size and electronegativity of Z had an effect on the stereochemistry of 1,2-addition to cyclohexene.High yields of addition to a variety of olefins were obtained with N-chloroamides such as ClCH2CONHCl, C2H5OCONHCl, CF3CONHCl.Their addition to enol ethers at -70 degC led to the synthesis of α-amido acetals or ketals (aldehydes or ketones) and to an α-amido glycoside in good yields.