42436-86-2

Basic information

• Product Name: 2-Phenylcyclobutanone
• Synonyms: 2-Phenylcyclobutanone;2-phenylcyclobutan-1-one;Cyclobutanone, 2-phenyl-
• CAS NO: 42436-86-2
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• Mol File: 42436-86-2.mol
• Article Data: 27

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-Phenylcyclobutanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylcyclobutanone(42436-86-2)
• EPA Substance Registry System: 2-Phenylcyclobutanone(42436-86-2)

Safety Data

• Hazardous Substances Data: 42436-86-2(Hazardous Substances Data)

Usage

Description

2-Phenylcyclobutanone is an organic compound that features a cyclobutanone ring with a phenyl group attached to the second carbon. It is known for its unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
2-Phenylcyclobutanone is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows for the creation of complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
2-Phenylcyclobutanone is used as a reagent for the green preparation of γ, δand ε-keto esters. These keto esters are important building blocks in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Flavor and Fragrance Industry:
Due to its unique aromatic properties, 2-Phenylcyclobutanone can be used as a component in the creation of novel fragrances and flavors, adding depth and complexity to the final product.
Used in Material Science:
2-Phenylcyclobutanone's structural characteristics make it a potential candidate for the development of new materials with specific properties, such as improved stability or reactivity in various applications.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 1667, 1995 DOI: 10.1016/0040-4039(95)00125-V

Upstream product

• 33462-81-6 cyclopropyldiphenylsulfonium tetrafluoroborate 
• 100-52-7 benzaldehyde 
• 33013-67-1 4,5-epoxy-3-phenyl-hexahydro-pyridazine 
• 186581-53-3 diazomethane 
• 103-82-2 phenylacetic acid 
• 18925-69-4 N,N-dimethyl-2-phenylacetamide 
• 74-85-1 ethene 
• 64-17-5 ethanol 
• 87639-40-5 4-phenyl-3-butyn-1-yl trifluoromethanesulfonate 
• 87639-41-6 4-p-tolylbut-3-yn-1-yl triflate 
• 85375-43-5 4-methyl-N-(4-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 104824-00-2 5-phenyl-2-trimethylsilyl-4,5-dihydrofuran 
• 556076-12-1 2-phenylcyclopropyl trimethylsilyl ketone 
• 246180-23-4 1-(Hydroxy-phenyl-methyl)-cyclopropanol 

Downstream Products

• 70106-31-9 1,1,2,2,3,3,4,4,4-Nonafluoro-butane-1-sulfonic acid 2-phenyl-cyclobut-1-enyl ester 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 64145-51-3 3-phenylcyclopentanone 
• 2819-12-7 trans-2-methyl-3-phenylcyclopentan-1-one 
• 2819-12-7 cis-2-methyl-3-phenyl-cyclopentanone 
• 106988-05-0 2,2-dimethyl-3-phenylcyclopentanone 
• 64154-47-8 trans-2,3-diphenylcyclopentan-1-one 
• 91445-79-3 2-Brom-2-phenyl-cyclobutanon 

Relevant articles and documents

ENTHALPY OF FORMATION OF KETENE, ETHYNOL, AND THEIR ANALOGS IN THE GAS PHASE

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Copper-Catalyzed Enantioselective Arylation via Radical-Mediated C-C Bond Cleavage: Synthesis of Chiral ω,ω-Diaryl Alkyl Nitriles

The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters to access ω,ω-diaryl alkyl nitriles has been developed in high yield (up to 92% yield) with excellent enantioselectivity (up to 91% ee). Side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, which provides an efficient route to construct diverse chiral ω,ω-diaryl alkyl nitriles. Synthetic utility has also been demonstrated in the further derivatization of the ω,ω-diaryl alkyl nitrile to the corresponding amide.

Synthesis of 2-Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

We report a novel process for the preparation of 2-substituted cyclobutanones. Such a method relies on the cross-coupling reaction of bromocyclobutenyl diethyl phosphate with either boronic acids or organozinc reagents. Dephosphorylation of the prepared 2-substituted cyclobutenyl phosphates affords 2-substituted cyclobutanones. We observed that the course of the dephosphorylation reaction depends on the properties of the substituents found on the cyclobutene nucleus. The presence of groups capable of stabilizing the negative charge is necessary for ring opening of cyclobutanones. The scope of the reported process for the preparation of 2-substituted cyclobutanones has also been extended to the preparation of cyclobutenyl sulfides.