1-Chlorocyclohexene

• CAS: 930-66-5
• Catalog Number: ACM930665
• Category: Main Products
• Molecular Weight: 116.59
• Molecular Formula: C₆H₉Cl
• Synonyms: 1-Chloro-1-cyclohexene;1-chlorocyclohex-1-ene;1-Chlorocyclohexene-1;1-CHLOROCYCLOHEXENE;1-Chloroclohexene;Cyclohexene,1-chloro-;1-CHLOROCYCLOHEXANE
• IUPAC Name: 1-chlorocyclohexene
• Canonical SMILES: C1CCC(=CC1)Cl
• InChI Key: BUAKPITZELZWNI-UHFFFAOYSA-N
• Boiling Point: 142.7ºC at 760 mmHg
• Flash Point: 35.9ºC
• Density: 1.02g/cm³
• Exact Mass: 116.03900

Case Study

1-Chlorocyclohexene for synthetic studies of anionic synthons

Chakravarthy, AS Jeevan, et al. Tetrahedron Letters 57.29 (2016): 3231-3234.

Aryl-substituted cyclohexenes are an important class of compounds in synthetic organic chemistry. Differently substituted aryl cyclohexenes have wide applicability in organic synthesis and natural product chemistry. The interest in the synthesis of novel anionic synthons prompted the exploration of the possibility of converting 1-bromo-2-chlorocyclohexene to some novel aryl-substituted cyclic vinyl silanes that would be useful as anionic synthons. The reaction of 1-chlorocyclohexene with aryl bromides was used for process studies.
For this purpose, Suzuki cross-coupling reactions of 1-bromo-2-chlorocyclohexene with 11 boronic acids 2a-k were carried out in sealed tubes at 110 °C using 1,4-dioxane solvent and Pd(dppf)2Cl2 catalyst. 1-Chlorocyclohexene reacted with aryl bromides similar to the Heck reaction in Pd(OAc)2/DMSO solvent/NaOAc/2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl to afford 3a-k in 36-54% isolated yields.

1-Chlorocyclohexene for the synthesis of novel functionalized polymer adsorbents

Frynas, Sławomir, and Monika Wawrzkiewicz. Polymers 15.6 (2023): 1591.

A novel phosphorus-containing adsorbent (CyP(Ph)4-DVB) was prepared by copolymerizing divinylbenzene (DVB) with bis(α,β-unsaturated phosphocyclohexene) (CyP(Ph)4) synthesized from 1-chlorocyclohexene. ATR-FTIR showed that the phosphono group was introduced into the adsorbent structure. The thermal properties of the adsorbent were studied using differential scanning calorimetry (DSC), and the results showed that (CyP(Ph)4-DVB) was more stable than poly(DVB). CyP(Ph)4-DVB can be used to remove cationic dyes.
A mixture of 20 g (0.172 mol) of 1-chlorocyclohexene 2 and 20 mL of CH3Cl was placed in a culture flask equipped with a dropping funnel and a reflux condenser. 9 mL (0.35 mol) of bromine was added to 10 mL of dry CH3Cl and the temperature was maintained at 5-10 °C using an ice bath. Next, the solution was stirred at 5 C for 2 h. The mixture was allowed to slowly warm to room temperature. Next, the solution was washed with saturated Na2SO3 and the organic layer was dried over MgSO4 and evaporated in vacuo. The residual oil was distilled under reduced pressure to give the product in a clean state and the oil crystallized after cooling in an ice bath to give 20.5 g of crude 3.

1-Chlorocyclohexene used for the preparation of α-substituted aldehydes

Brémand, Nathalie, Pierre Mangeney, and Jean F. Normant. Tetrahedron Letters 42.10 (2001): 1883-1885.

Lithium amide extracted from N,N,N'-trimethyl-1-amide is converted to lithium cycloalkamidoamide by cinnamaldehyde 2-diphenylethanediamine, followed by regioselective and stereoselective carbonization with the addition of various organolithium compounds synthesized from 1-chlorocyclohexene, etc. Subsequent hydrolysis or capture with MeI yields α-mono- or α,β-substituted 3-phenylpropanal, with an e.g. of 76-96%. This can be extended to silanized α-enols.
In THF, various organolithium compounds can be used with good yields and mirror selectivity: primary, secondary, and tertiary alkyllithiums. Lithium cyclohexanoyl prepared from 1-chlorocyclohexene is also reacted in diethyl ether (yield 49%, e.g., 96%). In this case, the reduction of the corresponding aldehyde must be carried out immediately after hydrolysis to avoid epiisomerization of the unstable enoic acid hydrogen atoms.

1-Chlorocyclohexene used in ring-expansion reactions

McIntosh, Kyle. (2020).

To construct spirocyclic systems, a photochemically initiated half-pinacol rearrangement reaction involving an intramolecular alcohol substrate was attempted. The synthesis of ring-expansion precursors using 1-chlorocyclohexene was successfully achieved. Most siloxy-epoxy ring-expansion reactions of cyclobutane rings to generate l-azaspiro[5.4]decane showed poor selectivity. Ring-expansion reactions of cyclobutane rings were performed on siloxy-epoxy carbocyclic and heterocyclic rings to elucidate the reaction mechanism.
1-Chlorocyclohexene reacted with lithium metal in diethyl ether to generate alkenyl lithium via lithium-chloride exchange. However, titration of alkenyl lithium indicated that lithium-chloride exchange had occurred to a certain extent. Furthermore, the formation of lithium chloride salts also supported the formation of alkenyl lithium.

Custom Q&A

What is the molecular formula of 1-Chlorocyclohexene?

The molecular formula of 1-Chlorocyclohexene is C6H9Cl.

When was 1-Chlorocyclohexene created according to the reference?

1-Chlorocyclohexene was created on March 26, 2005.

What is the IUPAC Name of 1-Chlorocyclohexene?

The IUPAC Name of 1-Chlorocyclohexene is 1-chlorocyclohexene.

What is the InChIKey of 1-Chlorocyclohexene?

The InChIKey of 1-Chlorocyclohexene is BUAKPITZELZWNI-UHFFFAOYSA-N.

What is the Canonical SMILES of 1-Chlorocyclohexene?

The Canonical SMILES of 1-Chlorocyclohexene is C1CCC(=CC1)Cl.

What is the molecular weight of 1-Chlorocyclohexene?

The molecular weight of 1-Chlorocyclohexene is 116.59 g/mol.

What is the CAS number of 1-Chlorocyclohexene?

The CAS number of 1-Chlorocyclohexene is 930-66-5.

What is the XLogP3-AA of 1-Chlorocyclohexene?

The XLogP3-AA of 1-Chlorocyclohexene is 2.6.

How many hydrogen bond donor count does 1-Chlorocyclohexene have?

1-Chlorocyclohexene has 0 hydrogen bond donor count.

Is 1-Chlorocyclohexene a canonicalized compound?

Yes, 1-Chlorocyclohexene is a canonicalized compound.