3306-02-3

Basic information

• Product Name: 1,2-Diphenylcyclobutene
• Synonyms: 1,1'-(1-Cyclobutene-1,2-diyl)bisbenzene;1,2-Diphenyl-1-cyclobutene;1,2-Diphenylcyclobutene
• CAS NO: 3306-02-3
• Molecular Formula: C₁₆H₁₄
• Molecular Weight: 206.28
• Mol File: 3306-02-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Diphenylcyclobutene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diphenylcyclobutene(3306-02-3)
• EPA Substance Registry System: 1,2-Diphenylcyclobutene(3306-02-3)

Safety Data

• Hazardous Substances Data: 3306-02-3(Hazardous Substances Data)

Usage

Description

1,2-Diphenylcyclobutene is an organic compound with the chemical formula C18H16. It is a colorless to pale yellow crystalline solid that is insoluble in water and has a molecular weight of 232.32 g/mol. 1,2-Diphenylcyclobutene is known for its unique chemical structure, which consists of a cyclobutene ring fused to two phenyl rings.

Uses

Used in Chemical Synthesis:
1,2-Diphenylcyclobutene is used as an intermediate in the synthesis of various organic compounds. It serves as a valuable building block for the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Food Packaging Industry:
1,2-Diphenylcyclobutene is used as a potential print-related contaminant in food packaging. 1,2-Diphenylcyclobutene trans-1,2-Diphenylcyclobutane (D487505), which is synthesized from 1,2-Diphenylcyclobutene, is being investigated for its potential presence in food packaging materials. This is important for ensuring the safety and quality of food products.

Upstream product

• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 74-85-1 ethene 
• 501-65-5 diphenyl acetylene 
• 5685-39-2 1-benzoyl-1-phenylcyclopropane 
• 451-40-1 phenyl benzyl ketone 
• 100-59-4 phenylmagnesium chloride 
• 591-51-5 phenyllithium 
• 647028-03-3 1-phenylsulfonyl-2-phenyl-1-cyclobutene 
• 6363-15-1 (1-phenylcyclopropyl)phenyl keton tosylhydrazone 
• 593-60-2 Vinyl bromide 
• 17988-44-2 (cyclohex-1-en-1-ylethynyl)trimethylsilane 
• 193211-89-1 (E)-1,2-diphenyl-1,4-diiodobut-1-ene 
• 495-71-6 phenacylacetophenone 
• 58368-31-3 2-phenyl-2-(1-phenyl-cyclopropyl)-oxirane 

Downstream Products

• 5685-39-2 1-benzoyl-1-phenylcyclopropane 
• 7694-30-6 cis-1,2-diphenylcyclobutane 
• 216876-65-2 C₄H₆BH(C₆H₅)2 
• 64630-84-8 2,5-Diphenyl-anti-tricyclo<4.3.0.0.^2.5>nonan 
• 95479-49-5 (E)-2,3-diphenylbut-2-ene-1,4-diol 
• 95479-45-1 2,3-diphenylbut-2-enedial 
• 62142-84-1 (Z)-2,3-diphenyl-2-butene-1,4-diol 
• 6583-62-6 (2R,3S)-2,3-diphenylbutane-1,4-diol 
• 5635-16-5 3,4-diphenyl-2(5H)-furanone 
• 222158-69-2 (1R,7S,8R,11S)-8,11-Diphenyl-3,5-dioxa-4-thia-tricyclo[5.4.0.0^8,11]undecane 4,4-dioxide 
• 13401-42-8 (1R,4S)-1,4-diphenylbutane-1,4-diol 
• 2085-90-7 (+/-)-1,4-diphenylbutane-1,4-diol 
• 222158-67-0 ((1S,2R,3S,4R)-3-Hydroxymethyl-1,4-diphenyl-bicyclo[2.2.0]hex-2-yl)-methanol 
• 495-71-6 phenacylacetophenone 

Relevant articles and documents

Addition of dichloro- and dibromocarbene to 1,2-diphenylcyclobutene

1,2-Diphenylcyclobutene (7) was reacted with dibromo- and dichlorocarbene, both generated via three different methods. 1,3-Diphenyl-2-halocyclopenta-1,3-dienes 12 were isolated which result from addition of the dihalocarbenes to the cyclobutene double bond of 7. A cationic cyclopropyl-allyl rearrangement (CCA) in gem-dihalobicyclopentanes 8 leads to 2,3-dihalocyclopentenes 9, which under the reaction conditions are dehydrohalogenated to 12. A second carbene addition and rearrangement afford aromatic compounds 11 and 16.

Attempted preparation of 5,5-difluoro-1,4-diphenylbicyclo[2.1.0]pentane - Serendipitous synthesis of 1,3-difluoro-2,4-diphenylbenzene

Addition of difluorocarbene to 1,2-diphenylcyclobutene, using PhHgCF3, results in formation of 1,3-difluoro-2,4-diphenylbenzene. A mechanism for this reaction is proposed.

Stereoselective Synthesis of anti-1,4-Diols by a BH3· THF-Mediated Rearrangement of 1,2-Disubstituted Cyclobutenes

A new stereoselective rearrangement of cyclobutylboranes, obtained by the hydroboration of 1,2-disubstituted cyclobutenes, provides anti-1,4-diols with good-to-excellent diastereoselectivity. The mechanism of the rearrangement is discussed based on theoretical calculations.