62056-46-6

Usage

Type of compound

Chlorinated cycloalkane

Substituent

tert-Butyl group

Physical state

Colorless liquid

Solubility

Insoluble in water, soluble in organic solvents

Uses

Intermediate in the production of chemicals (pharmaceuticals, pesticides), solvent in organic synthesis

Chemical properties

Interesting reactivity due to tert-butyl group and chlorine atom on the cyclohexane ring

Handling precautions

Potential hazardous effects on health and environment

InChI:InChI=1/C10H19Cl/c1-10(2,3)8-4-6-9(11)7-5-8/h8-9H,4-7H2,1-3H3

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 507-20-0 tertiary butyl chloride 
• 110-83-8 cyclohexene 
• 5009-39-2 trans-4-tert-butylcyclohexylmercury bromide 

Downstream Products

• 3178-22-1 tert-butylcyclohexane 
• 17530-01-7 4-tert-butyl-1-lithiocyclohexane 
• 17553-36-5 trans-tert-butyl(4-²H₁)cyclohexane 
• 53042-76-5 cis-tert-butyl(4-²H₁)cyclohexane 
• 135605-02-6 cis 1-methylseleno-4-tert-butyl cyclohexane 
• 126937-60-8 trans 1-methylseleno-4-tert-butyl cyclohexane 

Relevant academic research and scientific papers

An efficient method for chlorination of alcohols using PPh3/Cl3CCONH2

A new and convenient method for the chlorination of alcohols utilizing PPh3/Cl3CCONH2 is addressed. Various alcohols could smoothly be converted into their corresponding alkyl chlorides in high yield under mild conditions with short reaction times. A mechanism is disclosed with the evidence of inversion of configuration of the analogous alkyl chloride derived from R-(-)-2-octanol.

Direct conversion of carbonyl compounds into organic halides: Indium(III) hydroxide-catalyzed deoxygenative halogenation using chlorodimethylsilane

The reaction of carbonyls and chlorodimethylsilane was effectively catalyzed by indium(III) hydroxide and afforded the corresponding deoxygenative chlorination products, in which the carbonyl carbon accepted two nucleophiles (H and Cl) with releasing oxygen. Only In(OH)3 catalyzed the reaction, and typical Lewis acids such as TiCl4, AlCl3, and BF3·OEt2 showed no catalytic activity. The reaction mechanism of this deoxygenative chlorination includes initial hydrosilylation followed by chlorination. Other nucleophiles such as allyl or iodine were available for this methodology. The moderate Lewis acidity of indium catalyst enabled chemoselective reaction, and therefore ester, nitro, cyano, or halogen groups were not affected during the reaction course. Copyright

Diastereofacial selectivity in reactions of substituted cyclohexyl radicals. An experimental and theoretical study

The diastereofacial selectivity in reactions of a series of alkyl-substituted cyclohexyl radicals has been investigated. In additions of cyclohexyl radicals to alkenes, it has been found that only substituents bound at the olefinic center being attacked by the radical influence the equatorial-axial selectivity. Substituents bound to the radical center or axial substituents β to the radical center lead to increased axial attack. Equatorial β-substituents or axial γ-substituents increase the amount of equatorial attack. The same trends are observed for halogen and hydrogen abstraction reactions; the amount of axial reaction product is usually somewhat higher than in the addition reactions. The stereoselectivities can be explained with steric and torsional effects very similar to those suggested for nucleophilic addition reactions to cyclohexanones. A MM2 force field has been parameterized to gain further insight into the stereochemistry of the reaction.

Long-range Proton Hyperfine Splittings in the EPR Spectra of Cyclohexyl and Alkylcyclohexyl Radicals: Ring Inversion in the Cyclohexyl Radical

The cyclohexyl radical has been studied by EPR spectroscopy in liquid cyclopropane at low temperatures and hyperfine splittings from the γ-protons have been observed for the first time.The temperature-dependent EPR spectra have been computer simulated, taking account of β-, γ- and δ-proton exchange, to afford a new Arrhenius rate expression for chair-to-chair interconversion in this radical (θ=2.303 RT kJ mol-1). (A).The 4-tert-butylcyclohexyl radical is conformationally locked by the equatorial tert-butyl group and its EPR spectrum does not not exhibit temperature-dependent lineshape effects or resolvable splitting from the axial δ-proton.The cis-3,5-dimethylcyclohexyl radical is also locked in a chair conformation and its EPR spectrum shows long-range splittings from two axial γ-protons and from the equatorial δ-proton.Ab initio and semi-empirical (AM1) molecular orbital calculations predict a slightly non-planar equilibrium configuration at Cα in the cyclohexyl radical; Hα prefers equatorial placement, but the energetic cost of planarisation is very small.

Conformational Studies of Dicyclohexylthallium Chloride, Bis(4-methylcyclohexyl)thallium Chloride and Bis(4-tert-butylcyclohexyl)thallium Chloride by (1)H NMR

Vicinal thallium-hydrogen coupling constants are used to discuss conformations in dicyclohexylthallium chloride, bis(4-methylcyclohexyl)thallium chloride and bis(4-tert-butylcyclohexyl)thallium chloride.Thallium does not have a very strong preference for equatorial positions in dicyclohexylthallium chloride, whereas bis(4-alkylcyclohexyl)thallium chlorides exist largely in one conformation.Bis(4-methylcyclohexyl)thallium chloride exists in three isomeric forms; the major product appears to be the cis-isomer (equatorial methyl, axial thallium), with the other twoisomers probably containing thallium trans to the methyl group (axial thallium being preferred).The preference for the cis-isomer (equatorial tert-butyl, axial thallium) of bis(4-tert-butylcyclohexyl)thallium chloride is such that other isomers are not obtained.