3469-06-5

Basic information

• Product Name: Benzocyclobutenone
• Synonyms: Benzocyclobuten-1(2H)-one;Benzocyclobutenone;Bicyclo[4.2.0]octa-1,3,5-trien-7-one;1,2-Dihydrobenzocyclobutene-1-one;1,2-Ethanobenzene-7-one;Bicyclo[4.2.0]octa-1(6),2,4-triene-7-one;2-benzylcyclobutan-1-one;1-ONBCB Benzocyclobutenone
• CAS NO: 3469-06-5
• Molecular Formula: C₈H₆O
• Molecular Weight: 118.13
• Product Categories: Aluminium foil bag/Fluoride bottle or on your request
• Mol File: 3469-06-5.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 219.6 °C at 760 mmHg
• Flash Point: 85.9 °C
• Appearance: /
• Density: 1.214 g/cm³
• Vapor Pressure: 0.118mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzocyclobutenone(CAS DataBase Reference)
• NIST Chemistry Reference: Benzocyclobutenone(3469-06-5)
• EPA Substance Registry System: Benzocyclobutenone(3469-06-5)

Safety Data

• Hazardous Substances Data: 3469-06-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystals

InChI:InChI=1/C8H6O/c9-8-5-6-3-1-2-4-7(6)8/h1-4H,5H2

Upstream product

• 108-31-6 maleic anhydride 
• 38382-55-7 6-methylene-2,4-cyclohexadienylideneketene 
• 703-59-3 homophthalic anhydride 
• 75-87-6 chloral 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 72610-87-8 trans-1-(1-Benzocyclobutenylidene)benzocyclobutene 
• 72610-88-9 cis-1-(1-benzocyclobutenylidene)benzocyclobutene 
• 78752-32-6 benzocyclobutenone 
• 69139-15-7 Sodium Salt of Benzocyclobutenone Tosylhydrazone 
• 72610-89-0 Lithium Salt of Benzocyclobutenone Tosylhydrazone 
• 97567-66-3 Bicyclo[4.2.0]octa-1,3,5-trien-(7E)-ylidene-phenyl-amine 
• 95448-21-8 benzocyclobutenone N-tert-butylimine 
• 126889-57-4 2-(1'-Hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2,4-dimethylpentan-3-one 
• 68913-13-3 7,7-dichlorobenzocyclobutene 

Downstream Products

• 52679-82-0 7-ethylbicyclo<4.2.0>octa-1,3,5-trien-7-ol 
• 19164-61-5 7-phenylbicyclo<4.2.0>octa-1,3,5-trien-7-ol 
• 35447-99-5 1,2-dihydrobenzocyclobuten-1-ol 
• 142532-18-1 7-(4-Methoxyphenyl)bicyclo<4.2.0>octa-1,3,5-trien-7-ol 
• 91416-31-8 3-(trichloromethyl)-3,4-dihydroisocoumarin 
• 38368-84-2 1-ethenylbenzocyclobuten-1-ol 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 52665-62-0 (-)-(S)-1,2-dihydrobenzocyclobuten-1-ol 
• 178602-18-1 (R)-Bicyclo[4.2.0]octa-1,3,5-trien-7-ol 
• 118-90-1 ortho-methylbenzoic acid 
• 816-79-5 3-ethyl-2-pentene 
• 73318-30-6 3-(o-methylphenyl)-1H-2-benzopyran-1-one 
• 72610-88-9 cis-1-(1-benzocyclobutenylidene)benzocyclobutene 
• 72610-87-8 trans-1-(1-Benzocyclobutenylidene)benzocyclobutene 

Relevant articles and documents

A very short synthesis of steroids from 1,3-butadiene and benzocyclobutenes

Lewis acid mediated addition of 1,8-bis(trimethylsilyl)octa-2,6-diene (BISTRO) 1 to succinic anhydride led to spirolactone 2 [(±)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one]. Methoxycarbonylation followed by stereoselective alkylation by various benzocyclobutenes afforded the substituted benzocyclobutene steroid precursors 5. Thermolysis of 5 gave rise to steroids (±)-6 with a transanti-cis configuration in five steps and in a highly stereoselective manner. Modifications of the sequence allowed the preparation of steroids (±)-11 with trans-anti-trans configuration.

Synthetic approach to benzocyclobutenones using visible light and a phosphonate auxiliary

Reported herein is a two-step procedure to synthesize benzocyclobutenones from (o-alkylbenzoyl)phosphonates. It consists of a visible-light-driven cyclization reaction forming phosphonate-substituted benzocyclobutenols and subsequent elimination reaction of the H-phosphonate, which assumes a key role as the recyclable auxiliary. A wide variety of functionalized benzocyclobutenones, which include those difficult to synthesize by conventional methods, are efficiently synthesized.

Synthesis of a polymerizable benzocyclobutene that undergoes ring-opening isomerization at reduced temperature

1-Ethoxyvinylbenzocyclobutene is a substituted benzocyclobutene that undergoes radical polymerization to produce polymers that can be crosslinked at 100-150 °C. The 4- and 5-vinyl isomers are synthesized in a 1:4 ratio via a halogenated benzyne intermediate produced from anthranilic acid, followed by cycloaddition with ethyl vinyl ether and replacement of the halogen atom with a vinyl group. Georg Thieme Verlag Stuttgart · New York.