7641-77-2

Basic information

• Product Name: 1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE
• Synonyms: HEXAMETHYLDEWARBENZENE;1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE;2-Butin hexamethyl-dewar-benzol;2-butinhexamethyl-dewar-benzol;Bicyclo(2.2.0)hexa-2,5-diene, hexamethyl-;Bicyclo[2.2.0]hexa-2,5-diene, 1,2,3,4,5,6-hexamethyl-;Hexamethyl-bicyclo(2.2.0)hexa-2,5-dien;hexamethyl-bicyclo(2.2.0)hexa-5-diene
• CAS NO: 7641-77-2
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.27
• EINECS: 231-576-3
• Mol File: 7641-77-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 7 °C(lit.)
• Boiling Point: 60 °C20 mm Hg(lit.)
• Flash Point: 95 °F
• Appearance: /
• Density: 0.803 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.9mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: 1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE(7641-77-2)
• EPA Substance Registry System: 1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE(7641-77-2)

Safety Data

• Statements: 10
• Safety Statements: 16-33-36/37/39
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• RTECS: DT7320000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 7641-77-2(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Purification Methods

Purify it by passage through alumina [Traylor & Miksztal J Am Chem Soc 109 2770 1987].

InChI:InChI=1/C12H18/c1-7-8(2)12(6)10(4)9(3)11(7,12)5/h1-6H3

Upstream product

• 503-17-3 dimethylacetylene 
• 87-85-4 Hexamethylbenzene 
• 4116-93-2 deca-2,8-diyne 

Downstream Products

• 87-85-4 Hexamethylbenzene 
• 78580-06-0 (2R,3R,5R,6R)-1,2,3,5,6-Pentamethyl-4-methylene-3-phenylsulfanyl-tricyclo[3.1.0.0^2,6]hexane 
• 15971-76-3 5-acetyl-1,2,3,4,5-pentamethylcyclopentadiene 
• 87-85-4 hexamethylbenzene radical cation 
• 50336-48-6 3a,5,6,7c,7a-pentamethyl-4-methylene-3-(2,4,6-trimethyl-phenyl)-(3ar,7ac)-3a,4,7,7a-tetrahydro-benzo[d]isoxazole 
• 50336-49-7 (2E,5E,7E)-5,6,7,8,9-pentamethyl-4-methylene-3-(2,4,6-trimethyl-phenyl)-4,9-dihydro-[1,2]oxazonine 
• 3854-96-4 2,3,4,5,6,6-hexamethylcyclohexa-2,4-dien-1-one 
• 882-33-7 diphenyldisulfane 
• 87-85-4 hexamethylbenzene radical cation 
• 50336-47-5 1,2,3,4,5,6-hexamethyl-9-(2,4,6-trimethyl-phenyl)-7-oxa-8-aza-tricyclo[4.3.0.0^2,5]nona-3,8-diene 
• 50336-46-4 1,2,3,4,5,6-hexamethyl-9-(4-nitro-phenyl)-7-oxa-8-aza-tricyclo[4.3.0.0^2,5]nona-3,8-diene 
• 52056-13-0 2-Chloro-1,3,3,4,5-pentamethyl-6-methylene-cyclohexa-1,4-diene 

Relevant articles and documents

ESR Evidence for the 2A1 State of the Hexamethyl (Dewar) Benzene Radical Cation

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Quantum amplified isomerization: A new concept for polymeric optical materials

The preparation and evaluation of a new class of photoresponsive polymers are described on the basis of a process called quantum amplified isomerization (QAI). The QAI process utilizes photoinitiated, cation radical isomerization chemistry in a polymeric medium. Two classes of materials are described: one where the QAI reactant is molecularly doped in the polymer matrix and another where the reactant is part of a functionalized polymer. Quantum yield experiments demonstrate that the isomerization reaction can proceed by a chain process with modest efficiencies. Photochemical conversion experiments show that high extents of conversion of the QAI reactants are possible. The rate and extent of conversion are strongly correlated to the glass transition temperature of the polymer. For molecularly doped polymers, hypotheses to explain the high conversions based on diffusion or phase separation of the reactants were tested and excluded. Models are discussed to rationalize experimental factors that affect the quantum yields and the photochemical conversions.

Two-Step Route toward Some Propellanes and Their Conversion into Stable Tricyclic Cations

The synthesis of 1,4-tetramethylene(Dewar benzene) (2, a propellane) and its conversion to the propellanes 3 and 10 are described.Reaction of alcohol 10 with FSO3H/SO2ClF at low temperature (-135 deg C) yielded tricyclic cation 12, which rearranged at -75 deg C to a mixture of three isomeric cations.The structures and rearrangements of the cations were studied with 1H and 13C NMR spectroscopy and deuterium labeling.