658-18-4

Basic information

• Product Name: 1,4-bis(difluoroMethylene)cyclohexane
• Synonyms: 1,4-bis(difluoroMethylene)cyclohexane
• CAS NO: 658-18-4
• Molecular Formula: C₈H₈F₄
• Molecular Weight: 180.1427328
• Mol File: 658-18-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-bis(difluoroMethylene)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(difluoroMethylene)cyclohexane(658-18-4)
• EPA Substance Registry System: 1,4-bis(difluoroMethylene)cyclohexane(658-18-4)

Safety Data

• Hazardous Substances Data: 658-18-4(Hazardous Substances Data)

Usage

Type of compound

Bicyclic chemical compound

Structure

Cyclohexane ring with two difluoromethylene groups attached to the 1 and 4 positions

Physical state

Colorless liquid

Odor

Strong, sweet

Solubility

Insoluble in water

Uses

a. Solvent in various chemical processes
b. Reagent in organic synthesis
c. Production of other chemicals and pharmaceuticals

Safety precautions

a. Toxic if ingested or inhaled
b. Prolonged exposure may cause irritation to the skin and respiratory system
c. Handle with caution

Upstream product

• 75-61-6 dibromodifluoromethane 
• 637-88-7 1,4-Cyclohexanedione 

Downstream Products

• 718-55-8 trans-1,4-Dibrom-1,4-bis-(brom-difluor-methyl)-cyclohexan 
• 651-12-7 α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene 

Relevant articles and documents

[3,3] Sigmatropic rearrangement of some fluorinated 1,5-hexadienes

Fluorine atoms incorporated into 1,5-hexadiene molecule should influence the kinetic as well as the thermodynamic parameters of [3,3] sigmatropic rearrangement (Cope rearrangement). Within few decades is has been documented that this transformation proceeds in a concerted manner, rather than stepwise with some radical intermediates involved. Few new terminally fluorinated 1,5-hexadienes (compounds 3, 5A, 7, 9 and 5B) have been synthesized. The activation parameters of rearrangement have been determined and compared with those known for hydrocarbon analogues. While systems developing chair-like transition states (compounds 3 and 5) showed close similarity with hydrocarbon analogues (compound 1), those developing boat-like transition states (compounds 7, 9 and 5B) may proceed through radical stepwise mechanism. Computational studies of the transition states were carried out, showing that only ab initio methods (MP2 and especially DFT) can give approximate correlation with experimental data, whereas in the case of hydrocarbon analogues even simple semiempirical methods (AM1) were reliable enough to reproduce experimental results.