174790-32-0

Basic information

• Product Name: 1-(4-chlorobutyl)cyclopropanol
• Synonyms: 1-(4-chlorobutyl)cyclopropanol;Cyclopropanol, 1-(3-chloropropyl)-;1-(3-chloropropyl)cyclopropanol;1-(3-chloropropyl)cyclopropan-1-ol
• CAS NO: 174790-32-0
• Molecular Formula: C6H11ClO
• Molecular Weight: 134.60394
• Mol File: 174790-32-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-chlorobutyl)cyclopropanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorobutyl)cyclopropanol(174790-32-0)
• EPA Substance Registry System: 1-(4-chlorobutyl)cyclopropanol(174790-32-0)

Safety Data

• Hazardous Substances Data: 174790-32-0(Hazardous Substances Data)

Usage

General Description

1-(4-chlorobutyl)cyclopropanol is a chemical compound with the molecular formula C8H15ClO. It is a cyclopropanol derivative and contains a cyclopropane ring with a butyl and chloro substituent. 1-(4-chlorobutyl)cyclopropanol is used in organic synthesis and can be employed as a building block in the preparation of various other chemical compounds. It is also used as an intermediate in the production of pharmaceuticals and agrochemicals. 1-(4-chlorobutyl)cyclopropanol is a colorless to pale yellow liquid with a slightly musty odor and is considered to be a flammable substance. It is important to handle this chemical with caution and in accordance with safety regulations and guidelines.

Upstream product

• 3153-36-4 4-chloro-butyric acid ethyl ester 
• 925-90-6 ethylmagnesium bromide 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 3153-37-5 methyl 4-chlorobutyrate 

Relevant articles and documents

Synthesis of γ-Keto Sulfones through a Three-Component Reaction of Cyclopropanols, DABCO ? (SO2)2 and Alkyl Halides

A route to γ-keto sulfones through a metal-free reaction of cyclopropanols, DABCO ? (SO2)2 and alkyl halides is described. This reaction occurs under mild conditions in the absence of any catalysts, additives, or oxidants. Various functional groups including as ester, amino, methoxy, bromo, trifluoromethyl, nitro and carbonyl are tolerated well in this transformation, and the corresponding γ-keto sulfones are afforded in 35% to 95% yields. The proposed mechanism implies that this reaction proceeds through γ-keto sulfinate intermediate generated in situ, which further undergoes nucleophilic substitution with alkyl halides leading to γ-keto sulfones. (Figure presented.).

Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of a copper(ii) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluoroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones in up to 94% yields. The experimental protocol is mild and tolerates a number of functionalities in the cyclopropanol substrate. The reaction proceeds via a one-pot oxidation-Michael addition mechanism and can serve as a useful addition to the existing methods for the preparation of γ-keto sulfones based on the sulfa-Michael reaction.

Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols

Tertiary cyclopropanols react rapidly with Togni reagent in methanol at room temperature in the presence of catalytic amounts (3 mol%) of CuCl affording β-trifluoromethyl ketones in 65-73% isolated yields. Ring opening in 1,2-dialkylsubstituted cyclopropanols gives a mixture of isomeric β-trifluoromethyl ketones in about 50% combined yield.