1,2-DIMETHYLENE-CYCLOHEXANE

Base Information

• Chemical Name: 1,2-DIMETHYLENE-CYCLOHEXANE
• CAS No.: 2819-48-9
• Molecular Formula: C8H12
• Molecular Weight: 108.183
• Hs Code.: 2902199090
• Mol file: 2819-48-9.mol

Synonyms:Cyclohexane,1,2-dimethylene- (6CI,7CI,8CI); 1,2-Bismethylenecyclohexane;1,2-Dimethylenecyclohexane; 1,2-Dimethylidenecyclohexane

Chemical Property of 1,2-DIMETHYLENE-CYCLOHEXANE

Chemical Property:

• Vapor Pressure: 9.92mmHg at 25°C
• Refractive Index: 1.4718
• Boiling Point: 134.6°Cat760mmHg
• Flash Point: 17.5°C
• PSA: 0.00000
• Density: 0.81g/cm³
• LogP: 2.67280

Purity/Quality:

98%Min ^*data from raw suppliers

1,2-Bismethylenecyclohexane(~75%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1,2-DIMETHYLENE-CYCLOHEXANE

There total 36 articles about 1,2-DIMETHYLENE-CYCLOHEXANE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

cis-1,2-cyclohexanedimethanol (15753-50-1,25712-33-8) → 1,2-bis(methylene)cyclohexane (2819-48-9)

Guidance literature:

DOI:10.1021/jo00298a017

Reference yield: 67.0%

trans-1,2-diiodomethylcyclohexane (150012-41-2) → 1,2-bis(methylene)cyclohexane (2819-48-9)

Guidance literature:

With potassium hydroxide; In methanol; for 4h; Heating;

DOI:10.1002/recl.19931120401

Reference yield: 65.0%

1-bromo-1-methyl-2-(bromomethylsulfonyl)cyclohexane → 1,2-bis(methylene)cyclohexane (2819-48-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 0.5h; Cooling with ice;

DOI:10.15227/orgsyn.065.0090

upstream raw materials:

formaldehyd

1-methylcyclohex-1-ene

2-(hydroxymethyl)-1-methylenecyclohexane

2-<(Dimethylamino)methyl>1,1-methylenecyclohexanone

Downstream raw materials:

5a,6,7,8,9,10,11,11a-Octahydro-naphtho[2,3-g]quinoline-5,12-dione

6a,7,8,9,10,11,12,12a-Octahydro-N-(4-methoxyphenyl)-6-oxo-6H-5-oxabenzanthracen-6a-carboxamid

1-(3-bromo-n-propyl)-1-methyl-2-methylenecyclohexane

1-(2-methyl-1-cyclohexenyl)-2-pentanone

Refernces

Tetraacylethenes as dienophiles and hetero dienes in two-step Diels- Alder reactions

10.1002/(SICI)1099-0690(199912)1999:12<3343::AID-EJOC3343>3.0.CO;2-S

The research explores the synthesis and reactivity of tetraacylethenes, specifically tetraacetylethylene (7a) and diacetyldibenzoylethylene (7b), in Diels–Alder reactions. The study aims to provide a novel access to functionalized [4.3.3]propellanes and clarify conflicting reports on the oxidative coupling of benzoylacetone (15b). The researchers found that tetraacetylethylene (7a) behaves as a mechanistic chameleon, yielding two different Diels–Alder products with 1,2-dimethylenecyclohexane, and can react as both an electron-deficient dienophile and a 1-oxa-1,3-diene. Key chemicals used in the process include barium manganate, iodosobenzene, 1,2-dimethylenecyclohexane, and various derivatives of benzoylacetone. The conclusions drawn from the study are that tetraacetylethylene (7a) is a versatile reactant in Diels–Alder reactions, capable of forming different products depending on the reaction conditions, and that the reactions likely proceed via a zwitterionic intermediate, offering insights into the ambiguity observed in the Diels–Alder chemistry of such compounds.