29480-09-9

Basic information

• Product Name: Cyclobutanol, 1-(4-chlorophenyl)-
• CAS NO: 29480-09-9
• Molecular Formula: C10H11ClO
• Molecular Weight: 182.65
• Mol File: 29480-09-9.mol

Chemical Properties

• CAS DataBase Reference: Cyclobutanol, 1-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutanol, 1-(4-chlorophenyl)-(29480-09-9)
• EPA Substance Registry System: Cyclobutanol, 1-(4-chlorophenyl)-(29480-09-9)

Safety Data

• Hazardous Substances Data: 29480-09-9(Hazardous Substances Data)

Upstream product

• 1191-95-3 cyclobutanone 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-46-7 para-dichlorobenzene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 22217-78-3 5-(4-chlorophenyl)-3,4-dihydro-2H-pyrrole 
• 50921-39-6 1-(4-chlorophenyl)cyclobutane-1-carboxylic acid 
• 26086-96-4 1,8-bis(4-chlorophenyl)octane-1,8-dione 
• 40877-09-6 4-chloro-1-(4-chlorophenyl)butan-1-one 

Relevant articles and documents

Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf

The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).

Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents

We report the first terminal trifluoromethylation at aryl and alkyl ketones' ?, or more remote sites via the selective C-C bond cleavage of cycloalkanols. The noncovalent interactions between alcohols and hypervalent iodines(III) reagents were disclosed to activate both alcohols and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation.

TFA-Catalyzed [3+2] Spiroannulation of Cyclobutanols: A Route to Spiro[cyclobuta[a]indene-7,1′-cyclobutane] Skeletons

A straightforward method for the synthesis of spiro[cyclobuta[a]indene-7,1′-cyclobutane] derivatives from cyclobutanols has been developed via one-pot [3+2] spiroannulation. A series of new spiro[cyclobuta[a]indene-7,1′-cyclobutane] derivatives are facile

Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.

Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments

gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.

Method for synthesizing 4-cyclobutyl biphenyl fluorine-containing compound

The invention discloses a method for synthesizing a 4-cyclobutyl biphenyl fluorine-containing compound. The method comprises the following steps: by taking chlorine benzene halide as an initial raw material, performing a Grignard reaction; performing a co

Mild Ring Contractions of Cyclobutanols to Cyclopropyl Ketones via Hypervalent Iodine Oxidation

An iodine-mediated oxidative ring contraction of cyclobutanols has been developed. The reaction allows the synthesis of a wide range of aryl cyclopropyl ketones under mild and eco-friendly conditions. A variety of functional groups including aromatic or alkyl halides, ethers, esters, ketones, alkenes, and even aldehydes are nicely tolerated in the reaction. This is in contrast with traditional synthetic approaches for which poor functional group tolerance is often a problem. The practicality of the method is also highlighted by the tunability of iodine oxidation system. Specifically, combining the iodine(III) reagent with an appropriate base allows the reaction to accommodate a range of challenging electron-rich arene substrates. The facile scalability of this reaction is also exhibited herein. (Figure presented.).

A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl–Alkyl Cross-Coupling Reactions

Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon–carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)?C(sp3) cross-coupling processes, with excellent functional-group tolerance.

Manganese-catalyzed oxidative azidation of cyclobutanols: Regiospecific synthesis of alkyl azides by C-C bond cleavage

A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, oth