3470-35-7

Basic information

• Product Name: 4,4-dichloro-3-phenylcyclobut-2-en-1-one
• Synonyms: 2-Cyclobuten-1-one, 4,4-dichloro-3-phenyl-
• CAS NO: 3470-35-7
• Molecular Formula: C₁₀H₆Cl₂O
• Molecular Weight: 213.06
• Mol File: 3470-35-7.mol

Chemical Properties

• Boiling Point: 274.7°C at 760 mmHg
• Flash Point: 114.1°C
• Density: 1.41g/cm³
• Vapor Pressure: 0.00532mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 4,4-dichloro-3-phenylcyclobut-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-dichloro-3-phenylcyclobut-2-en-1-one(3470-35-7)
• EPA Substance Registry System: 4,4-dichloro-3-phenylcyclobut-2-en-1-one(3470-35-7)

Safety Data

• Hazardous Substances Data: 3470-35-7(Hazardous Substances Data)

Upstream product

• 340-01-2 4,4-dichloro-3,3-difluoro-1-phenyl-cyclobutene 
• 536-74-3 phenylacetylene 
• 76-02-8 trifluoroacetyl chloride 
• 931-49-7 1-ethenylcyclohexene 
• 2713-84-0 4,4-dichloro-1-cyclohex-1-enyl-3,3-difluoro-cyclobutene 
• 1536-58-9 3,6-Dibromo-1-(4,4-dichloro-3,3-difluoro-cyclobut-1-enyl)-cyclohexene 

Downstream Products

• 103505-50-6 4,4-dichloro-3-phenyl-but-3-enoic acid 
• 109385-02-6 4,4-Dichloro-3-phenyl-but-3-enoic acid ethyl ester 
• 109384-96-5 2-(2,2-Dichloro-1-phenyl-vinyl)-3,4-dimethyl-cyclobutanone 
• 109384-93-2 7-exo-(2',2'-dichloro-1'-phenylvinyl)-cis-bicyclo<4.2.0>-oct-4-en-8-one 
• 109384-93-2 7-endo(2',2'-dichloro-1'-phenylvinyl)-cis-bicyclo<4.2.0>-oct-4-en-8-one 
• 109384-99-8 (E)-4,4-Dichloro-3-phenyl-but-2-enoic acid allylamide 
• 109384-98-7 N-allyl-3-phenyl-4,4-dichloro-3-butenamide 
• 109384-94-3 2-(2,2-Dichloro-1-phenyl-vinyl)-3,3-dimethyl-cyclobutanone 
• 158877-53-3 2-Chloro-4-acetoxy-3-phenyl-2-cyclobutenone 
• 16547-34-5 2,4-dichloro-3-phenyl-2-cyclobuten-1-one 
• 102170-63-8 2-Chloro-4-bromo-3-phenyl-2-cyclobutenone 
• 98949-07-6 2-Chloro-4-iodo-3-phenyl-2-cyclobutenone 
• 475634-06-1 3,3-dichloro-2-phenyl-5,8-dioxa-spiro[3.4]oct-1-ene 
• 103647-10-5 4-Methoxy-3-phenyl-2-butenoic acid lactone 

Relevant articles and documents

-Cycloaddition Reaction of Sulfilimines with Cyclobutenones: Access to Benzazepinones

A catalyst-free [4+3]-cycloaddition reaction of N-aryl sulfilimines with cyclobutenones is described, which provides a straightforward protocol for synthesizing 1,5-dihydro-2H-benzo[b]azepin-2-ones under mild reaction conditions. This reaction features a

Enantioselective Synthesis of 3-Substituted Cyclobutenes by Catalytic Conjugate Addition/Trapping Strategies

A copper-catalyzed tandem process to generate chiral cyclobutene derivatives has been developed. It is based on an enantioselective conjugate addition or reduction of a cyclobutenone and sequential trapping with a chlorophosphate in a one-pot process. These phosphates are stable under mildly acidic conditions and serve as good electrophiles in Negishi coupling reactions.

Enantioselective Synthesis of 4-Hydroxy-dihydrocoumarins via Catalytic Ring Opening/Cycloaddition of Cyclobutenones

A highly diastereo- and enantioselective ring-opening/cycloaddition reaction of cyclobutenones with 2-hydroxyacetophenones or salicylaldehyde was achieved by employing a chiral N,N′-dioxide-scandium(III) complex as the catalyst. It provided various 3-phen

Rhodium(i)-catalysed intermolecular alkyne insertion into (2-pyridylmethylene)cyclobutenes

Cyclobutenes with 2-pyridylmethylene groups at the 3 position underwent an intermolecular alkyne insertion reaction in the presence of a rhodium(i) catalyst at 170 °C to afford substituted benzenes. Among the different 2-pyridylmethylene groups examined, 3-methyl-2-pyridyl derivatives showed superior activity and readily coupled with various alkynes, including sterically demanding, heteroaromatic and terminal alkynes.

Regiodivergent cyclobutanone cleavage: Switching selectivity with different Lewis acids

The exploitation of strain release in small rings as driving force to enable complex transformations is a powerful synthetic tool. Among them, cyclobutanones are particularly versatile substrates that can be elaborated in a wide variety of structurally diverse building blocks. Herein, Lewis acid catalyzed rearrangement reactions are presented that provide selective access to two structurally distinct polycyclic scaffolds, that is, indenylacetic acid derivatives and benzoxabicyclo[3.2.1]octan-3-ones. The choice of the Lewis acid fully controls the reaction pathway and the regioselectivity of the cyclobutanone C-C bond cleavage site.

Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones

Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C-C bond of cyclobutenone.

New access to a tricyclo[3.2.1.02,7]oct-3-ene structure

A thermally induced reaction cascade including an electrocyclic rearrangement, two Diels-Alder reactions and a 1,4-elimination from a simple cyclobutene carbonate can explain the synthesis of a complex tricyclo[3.2.1.02,7]oct-3-ene core structu

The intermediacy of oxycyclobutenes in the synthesis and reactions of cyclobutenones and cyclobutenols

Vinylcyclobutenol 7, generated via the singlet oxygenation of alkylidenecyclobutene 5, rearranges at room temperature to a solvent dependent mixture of isomeric dienones 10 and 11. Alkylidenecyclobutene 5 was prepared in turn via an inverse Wittig additio

Facile addition of dichloroketene to acetylenes mediated by zinc and ultrasound

The addition of dichloroketene, generated from trichloroacetyl chloride, zinc dust and ultrasound, to terminal and internal acetylenes is reported. This procedure is a more convenient alternative to Zn-Cu couple.

A GENERAL METHOD FOR THE REDUCTIVE DECHLORINATION OF 4,4-DICHLOROCYCLOBUTENONES

Exposure of 4,4-dichlorocyclobutenones to the action of zinc dust in ethanol containing 5 equiv each of AcOH and TMEDA results in smooth reductive dechlorination producing simple cyclobutenones.