2819-48-9

Basic information

• Product Name: 1,2-DIMETHYLENE-CYCLOHEXANE
• Synonyms: 1,2-DIMETHYLENE-CYCLOHEXANE;1,2-Bis(methylene)cyclohexane
• CAS NO: 2819-48-9
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18088
• Product Categories: Aromatics, Miscellaneous Reagents
• Mol File: 2819-48-9.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 137.85°C (rough estimate)
• Flash Point: 17.5°C
• Appearance: /
• Density: 0.8361
• Vapor Pressure: 9.92mmHg at 25°C
• Refractive Index: 1.4718
• CAS DataBase Reference: 1,2-DIMETHYLENE-CYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIMETHYLENE-CYCLOHEXANE(2819-48-9)
• EPA Substance Registry System: 1,2-DIMETHYLENE-CYCLOHEXANE(2819-48-9)

Safety Data

• Hazardous Substances Data: 2819-48-9(Hazardous Substances Data)

Usage

Uses

1,2-Dimethylene-cyclohexane, is a conjugated dienes, which is a useful starting material for a variety of structures.

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 6165, 1983 DOI: 10.1021/ja00357a041

InChI:InChI=1/C8H12/c1-7-5-3-4-6-8(7)2/h1-6H2

Upstream product

• 78426-32-1 2-(hydroxymethyl)-1-methylenecyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 54730-18-6 bromomethanesulfonyl bromide 
• 103261-98-9 1-Methylene-2-(acetoxymethyl)cyclohexane 
• 150012-41-2 trans-1,2-diiodomethylcyclohexane 
• 343250-59-9 CYCLOHEXANE-1,2-DIMETHANOL, DIACETATE 
• 108-94-1 cyclohexanone 
• 29474-11-1 (2-methylcyclohex-1-en-1yl)methanol 
• 67-71-0 dimethylsulfone 
• 583-60-8 2-Methylcyclohexanone 
• 102683-61-4 1-Bromo-1-methyl-2-(bromomethylsulfonyl)-cyclohexane 
• 769092-24-2 2-[(dimethylamino)methyl]cyclohexanone 
• 85-42-7 1,2-Cyclohexanedicarboxylic acid-anhydride 
• 3971-29-7 1,2-bis(hydroxymethyl)cyclohexane 

Downstream Products

• 78156-47-5 5a,6,7,8,9,10,11,11a-Octahydro-naphtho[2,3-g]quinoline-5,12-dione 
• 80754-56-9 2-Phenyl-1,3,4,5,6,7-hexahydro-isophosphindole 2-oxide 
• 27723-50-8 1-Methylen-spiro<5.5>undecan 
• 97095-07-3 8a,9,10,11,12,13,14,14a-Octahydro-N-(4-methoxyphenyl)-8-oxo-8H-7-oxanaphth<1,2-a>anthracen-8a-carboxamid 
• 78172-07-3 2,5,12-trioxo-5a,6,7,8,9,10,11,11a-octahydro-1H-naphtho<2,3-g>quinoline 
• 134847-45-3 2-Diphenylvinylidene-2,3,4,5,6,7-hexahydro-1H-indene 
• 84183-26-6 3-<(E)-α-Chlorbenzyliden>-1,2,3,4,5,6,7,8-octahydro-2,2-dimethylnaphthalin 
• 96722-11-1 5,6,6a,7,8,9,10,11,12,12a-Decahydro-6-oxo-5-thiabenzanthracen-6a-carbonsaeure-(4-methoxyanilid) 
• 10563-11-8 bicyclo<4.2.0>oct-1(6)-ene 
• 52329-96-1 1-methyl-2-((phenylcarbonyl)methyl)-1-cyclohexene 
• 140902-50-7 2,3,4,5,6,7-hexahydro-2-phenyl-1H-inden-2-ol 
• 774-55-0 6-Acetyl-1,2,3,4-tetrahydronaphthalene 

Relevant articles and documents

Quest for diatomic selenium

Metallocene pentaselenides and elemental selenium were employed in an effort to generate diatomic selenium (Se2) under thermal conditions. Trapping experiments were carried out with six dienes. A successful formation of a diselenium adduct was observed in the case of 5,6-dimethylene-cyclohexa-1,3- diene (1a). The other dienes produced the corresponding dihydroselenophenes. The in-depth study of the limitations of our method to generate Se2 is described; a plausible mechanism rationalizing the observed results is proposed.

Studies of the condensation of sulfones with ketones and aldehydes

The condensation of ketones or aldehydes with sulfunes was shown to give a variety of products. Condensation of 2-methylcyclohexanone with dimethyl sulfone using potassium t-butoxide as base gave useful yields of 1,2- dimethylenecyclohexane. Under the same conditions, cycloheptanone, 3-methyl-2-butanone, and 2-bulanone were converted to dienes. Remarkably, these reaction conditions converted acetophenone into p-terphenyl (10%) and (E)-1,4-diphenyl-3-penten-1-one (44%). Propiophenone was converted to 2′-methyl-p-terphenyl (61%). Using α-tetralone produced 1-methynaphthalene and naphthalene. No reaction took place with β-tetralone. Using diethyl sulfone with α-tetralone lead to pure naphthalene. Condensation of isobutyraldehyde and dimethyl sulfone using potassium t-butoxide gave isoprene in low yield. Using benzaldehyde and benzyl phenyl sulfone in N,N-dimethylcinnamide gave 1,2-diphenyl-1- phenylsulfonylethylene, N,N-dimethylcinnamide, and a complex condensation product. Only 1,2-diphenyl-1-phenylsulfonylethylene was obtained when the solvent was THF.

(2-Vinylcyclopropyl)carbenes. More stepwise mechanisms for ring-expansion

A simple vinyl group is sufficient to induce a stepwise mechanism for the ring expansion of cyclopropylcarbenes.