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

Description

1,2-Dimethylene-cyclohexane, also known as methylnorbornene, is a conjugated diene that serves as a versatile starting material for synthesizing a wide range of chemical structures. It is a colorless liquid with a distinctive odor and is commonly used in the production of various polymers and chemicals.

Uses

1. Used in Polymer Industry:
1,2-Dimethylene-cyclohexane is used as a monomer for the production of specialty polymers, such as norbornene-based polymers, due to its unique cyclic structure and reactivity. These polymers have applications in various fields, including coatings, adhesives, and elastomers.
2. Used in Chemical Synthesis:
1,2-Dimethylene-cyclohexane is used as a building block in the synthesis of various chemicals, such as pharmaceuticals, agrochemicals, and fragrances. Its conjugated diene structure allows for a range of chemical reactions, making it a valuable intermediate in the chemical industry.
3. Used in Material Science:
1,2-Dimethylene-cyclohexane is used as a precursor in the development of advanced materials, such as high-performance plastics and composites. Its unique properties contribute to the enhanced performance of these materials in various applications, including automotive, aerospace, and electronics.
4. Used in Research and Development:
1,2-Dimethylene-cyclohexane is utilized as a model compound in academic and industrial research to study the properties and reactivity of conjugated dienes. This helps in the development of new synthetic methods, catalysts, and applications for these types of compounds.

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

• 43078-33-7 2-<(Dimethylamino)methyl>1,1-methylenecyclohexanone 
• 127-19-5 N,N-dimethyl acetamide 
• 583-60-8 2-Methylcyclohexanone 
• 591-49-1 1-methylcyclohex-1-ene 
• 54730-18-6 bromomethanesulfonyl bromide 
• 102683-61-4 1-Bromo-1-methyl-2-(bromomethylsulfonyl)-cyclohexane 
• 769092-24-2 2-[(dimethylamino)methyl]cyclohexanone 
• 108-94-1 cyclohexanone 
• 85-42-7 1,2-Cyclohexanedicarboxylic acid-anhydride 
• 3971-29-7 1,2-bis(hydroxymethyl)cyclohexane 
• 67-71-0 dimethylsulfone 
• 219905-14-3 1,4,5,6,7,8-hexahydro-benzo[d][1,2]oxathiin 3-oxide 
• 29474-11-1 (2-methylcyclohex-1-en-1yl)methanol 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 55370-36-0 1,2-Bis-(brommethyl)-1-cyclohexen 
• 1367737-07-2 3-phenyl-3,4,5,6,7,8-hexahydro-1H-isochromene 
• 1307279-28-2 2-methylenespiro[cyclohexane-1,3'-isochroman]-1'-one 
• 144241-81-6 2,2-diphenyl-2,3,4,5,6,7-hexahydro-2-sila-1H-indene 
• 1237816-34-0 C₂₂H₂₃NO 

Relevant articles and documents

Synthesis of highly substituted cyclobutane fused-ring systems from n-vinyl β-lactams through a one-pot domino process

In this contribution, aminocyclobutanes, as well as eight-membered enamide rings, have been made from N-vinyl β-lactams. The eightmembered products have been formed by a [3,3]-sigmatropic rearrangement, whereas the aminocyclobutanes have been derived from a domino [3,3]-rearrangement/6π- electrocyclisation process. The aminocyclobutanes have been obtained in a highly diastereoselective fashion. The cyclobutane ring system tolerates fusion even if adjacent quaternary centres are present. Systems containing up to four fused rings are readily accessible. The reaction profile has been investigated by using Gaussian 03. This study suggests that two reaction pathways for aminocyclobutane formation are possible. In one pathway the [3,3]-sigmatropic rearrangement is the rate-limiting step and in the second pathway the electrocyclisation is rate limiting. Taken together, these reactions should facilitate the construction of fused heterocycles.

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.