462-80-6

Basic information

• Product Name: cyclohexa-1,3-dien-5-yne
• Synonyms: cyclohexa-1,3-dien-5-yne;1,3-Cyclohexadien-5-yne;3,5-Cyclohexadiene-1-yne;Benzyne;o-Benzyne;1,2-didehydrobenzene
• CAS NO: 462-80-6
• Molecular Formula: C₆H₄
• Molecular Weight: 76.1
• Mol File: 462-80-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 118.8°C at 760 mmHg
• Flash Point: 9°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 19.6mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: cyclohexa-1,3-dien-5-yne(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexa-1,3-dien-5-yne(462-80-6)
• EPA Substance Registry System: cyclohexa-1,3-dien-5-yne(462-80-6)

Safety Data

• Hazardous Substances Data: 462-80-6(Hazardous Substances Data)

Usage

Chemical Properties

An unsaturated, cyclic hydrocarbon with a structure similar to benzene, in which one of the double bonds is replaced by a triple bond. It may be prepared from benzenediazonium-2-carboxylate or from isatoic anhydride.

Definition

A short-lived intermediate present in some reactions. The ring of six carbon atoms contains two double bonds and one triple bond (the systematic name is 1,2-didehydrobenzene).

InChI:InChI=1/C6H4/c1-2-4-6-5-3-1/h1-4H

Upstream product

• 591-50-4 iodobenzene 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 85-44-9 phthalic anhydride 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 100-66-3 methoxybenzene 
• 462-06-6 fluorobenzene 
• 17333-73-2 phenylium 
• 1239886-72-6 [[MeC(N(2,6-ⁱPr₂C₆H₃))CHC(Me)(NCH₂CH₂NMe)]Sc=N(2,6-ⁱPr₂C₆H₃)(DMAP)] 
• 6383-11-5 benzocyclobutene-1,2-dione 
• 1072-85-1 o-fluorobromobenzene 
• 164594-13-2 Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 109057-65-0 C₁₆H₁₂N₂O 

Downstream Products

• 54400-57-6 2-(4-methoxy-phenyl)-4λ⁴-benzo[3,4][1,2]dithiolo[1,5-b][1,2,4]dithiazole 
• 15364-55-3 9-bromotriptycene 
• 55322-56-0 α-Phenyl-β-aethylallylacetat 
• 945030-93-3 2-methyl-1-phenylbut-2-enyl acetate 
• 35162-70-0 [(3E,7E)-4,8,12-Trimethyl-1-((1E,5E)-2,6,10-trimethyl-undeca-1,5,9-trienyl)-trideca-3,7,11-trienylsulfanyl]-benzene 
• 37755-73-0 1,2,3,4,9-pentaphenyl-1,4-dihydro-1,4-epiphosphano-naphthalene 9-oxide 
• 55523-19-8 12-phenyl-10H-5,10-etheno-acridophosphine 
• 54400-55-4 2-phenyl-4λ⁴-benzo[3,4][1,2]dithiolo[1,5-b][1,2,4]dithiazole 
• 95-15-8 Benzo[b]thiophene 
• 1195-14-8 2-Methylbenzothiophene 
• 4783-68-0 2-phenoxypyridine 
• 13131-02-7 1-phenyl-1H-pyridin-2-one 
• 37520-79-9 (1S,8R)-9-Aza-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,11-tetraen-10-one 
• 2818-88-4 2-methylbenzoselenazole 

Relevant articles and documents

Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation

A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C-H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2,3-carbazolyne and 2,3-fluorenyne core, which pave the way for novel derivatizations of motifs relevant to materials chemistry.

Microwave-induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions

A non-conventional modification of exfoliated few-layer graphene (FLG) with different arynes under microwave (MW) irradiation and solvent-free conditions is reported. The described approach allows reaching fast, efficient and mild covalent functionalization of FLG.

ROOM TEMPERATURE POLYMER CROSSLINKING USING 1-FUNCTIONALIZED BENZOCYCLOBUTENE

Specific benzocyclobutenes serve as intramolecular or intermolecular or both intramolecular or intermolecular crosslinkers. The benzocyclobutenes can be incorporated into polymers post polymerization or can be provided as monomers that participate in homo