54580-22-2

Basic information

• Product Name: 2,5-dimethyl-4-(propan-2-yl)-3-(propan-2-ylidene)hexa-1,4-diene
• Synonyms: 1,4-Hexadiene, 2,5-dimethyl-4-(1-methylethyl)-3-(1-methylethylidene)-
• CAS NO: 54580-22-2
• Molecular Formula: C₁₄H₂₄
• Molecular Weight: 192.3404
• Mol File: 54580-22-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 263.4°C at 760 mmHg
• Flash Point: 103.2°C
• Density: 0.796g/cm³
• Vapor Pressure: 0.0168mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: 2,5-dimethyl-4-(propan-2-yl)-3-(propan-2-ylidene)hexa-1,4-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dimethyl-4-(propan-2-yl)-3-(propan-2-ylidene)hexa-1,4-diene(54580-22-2)
• EPA Substance Registry System: 2,5-dimethyl-4-(propan-2-yl)-3-(propan-2-ylidene)hexa-1,4-diene(54580-22-2)

Safety Data

• Hazardous Substances Data: 54580-22-2(Hazardous Substances Data)

Upstream product

• 1000-87-9 2,4-dimethyl-2,3-pentadiene 
• 107464-95-9 1-(2,4-dimethylpent-1-en-3-ylidene)-2,2,3,3-tetramethylcyclopropane 
• 94526-06-4 1-isopropylidene-2,2,4,4,5,5-hexamethylspiropentane 
• 114522-88-2 1-(2-hydroxy-2,4-dimethylpent-3-ylidene)-2,2,3,3-tetramethyl-cyclopropane 
• 69856-67-3 3,3,3',3',5,5,5',5'-octamethyl-3,3',5,5'-tetrahydro-4,4'-bi(4H-pyrazolylidene) 
• 94526-05-3 2,2,2',2',4,4,4',4'-octamethyl-3,3'-bithietanylidene 1,1,1',1'-tetraoxide 
• 114522-87-1 3'-ethoxycarbonyl-3'-isopropyl-3,3,5,5-tetramethyl-3,5-dihydropyrazole-4-spiro-2'-thi-irane 
• 107464-93-7 3,5-dihydro-3,3,5,5-tetramethyl-4-(1-ethoxycarbonyl-2-methylpropylidene)pyrazole 
• 19547-10-5 ethyl α-diazoiso-propylacetate 
• 94526-03-1 2,2,2'',2'',4,4,4'',4''-octamethyl-2',5'-dihydro<1,3,4>thiadiazole-2',5'-dispiro-3,3''-bis(thietane) 1,1,1'',1''-tetraoxide 
• 94526-02-0 3-diazo-2,2,4,4-tetramethylthietane 1,1-dioxide 
• 94525-98-1 (2,2,4,4-Tetramethyl-1,1-dioxo-1λ⁶-thietan-3-ylidene)-hydrazine 
• 58721-02-1 2,2,4,4-tetramethylthietan-3-one 1,1-dioxide 
• 1133-23-9 1,2-di-isopropylidene-3,3,4,4-tetramethylcyclobutane 

Downstream Products

• 527-84-4 2-methylisopropylbenzene 
• 106-42-3 para-xylene 
• 54580-23-3 3,4-Diisopropyl-2,5-dimethyl-2,4-hexadien 

Relevant articles and documents

THE GENERATION AND SIGMATROPIC REARRANGEMENT OF A DERIVATIVE OF VINYL-TMM (2,5-DIMETHYL-3-ISOPROPYL-4-ISOPROPYLIDENEHEX-2-EN-1,5-DIYL)

The thermal rearrangement of 2,5-dimethyl-3-isopropyl-4-isopropylidenehex-2-en-1,5-diyl to 4-isopropyl-3-isopropylidene-2,5-dimethylhexa-1,4-diene involves a 1,6-sigmatropic shift of hydrogen which may occur in antarafacial manner.

Preparation, Pyrolysis, and Photolysis of Three Sterically Crowded Alkenes, 3,3,3',3',5,5,5',5'-Octamethyl-3,3',5,5'-tetrahydro-4,4'-bi(4H-pyrazolylidene) 2,2,4,4-Tetramethyl-3-(3,3,5,5-tetramethyl-3,5-dihydro-4H-pyrazol-4-ylidene)-thietane 1,1-Dioxide and 2,2,2',2',4,4,4',4'-Octameth...

Photolysis and pyrolysis of the title compounds involve a stepwise elimination of nitrogen and/or sulphur dioxide and reactions which can be interpreted in terms of a series of trimethylenemethane (TMM) biradical intermediates.However, the photosensitised photolysis of the bi(pyrazolylidene) (11) give products indicative of an elimination of both nitrogens and the generation of a tetramethylene-ethane (TME) biradical intermediate.New synthesis of a number of highly sterically crowded alkenes including 2,2,4,4-tetramethyl-3-(3,3,5,5-tetramethyl-3,4-dihydro-4H-pyrazol-4-ylidene)thietane 1,1-dioxide (12) and 2,2,2',2',4,4,4',4'-octamethyl-3,3'-bithietanylidene 1,1,1',1'-tetraoxide (13), are described.Flash vacuum pyrolysis (f.v.p) of 3,3,3',3',5,5,5',5'-octamethyl-3,3'-5,5'-tetrahydro-4,4'-bi(4H-pyrazolylidene) (11) at 400 deg C gives 3,3,5,5-tetramethyl-4-(2,2,3,3-tetramethylcyclopropylidene)-3,5-dihydro-4H-pyrazole (21), at ca. 400 deg C 1-isopropylidene-2,2,4,4,5,5-hexamethylspiropentane (22), and at ca. 580 deg C a ca. 5:1 mixture of 4-isopropyl-3-isopropylidene-2,5-dimethylhexa-1,4-diene (23) and 2-(2,3-dimethylbut-1-en-3-yl)-1-isopropyl-3,3-dimethylcyclopropene (27).Above 700 deg C a complex mixture of aromatic products and low molecular weight hydrocarbons is produced which includes ethane, ethylene, propene, isobutane, and isobutene, p-xylene, o-cumene and probably m-cumene, and 2,5-dimethylisopropylbenzene.F.v.p. of the dihydropyrazole sulphone (12) gives initially 2,2,4,4-tetramethyl-3-(2,2,3,3,-tetramethylcyclopropylidene)thietane 1,1-dioxide (41) and at higher temperatures similar mixtures to those obtained from the bipyrazolylidene (11).Similar results were also obtained for the f.v.p. of the bis-sulphone (13).Photolysis of the bipyrazolylidene (11) gave initially the dihydropyrazole (21) and then a 48:52 mixture of the spiro compound (22) and 2,2,2',2',3,3,3',3'-octamethylbicyclopropylidene (42).Photolysis of the dihydropyrazole sulphone (12) gave 2,2,4,4-tetramethyl-3-(2,2,3,3-tetramethylcyclopropylidene)thietane 1,1-dioxide (41).Benzophenone-sensitised photolysis of the bipyrazolylidene (11) gave 1,2-di-isopropylidene-3,3,4,4-tetramethylcyclobutane (32).