4452-32-8

Usage

Uses

Used in Plastics Industry:
Cyclohex-1-en-1-yl diethyl phosphate is used as a flame retardant to enhance the fire resistance of various types of plastics, thereby improving their safety characteristics and reducing the risk of fire-related incidents.
Used in Foams Industry:
In the foams industry, cyclohex-1-en-1-yl diethyl phosphate serves as a flame retardant, ensuring that foam materials used in furniture, construction, and other applications meet fire safety standards and exhibit reduced flammability.
Used in Textiles Industry:
Cyclohex-1-en-1-yl diethyl phosphate is utilized as a flame retardant in textiles, making them more resistant to fire and suitable for use in environments with strict fire safety requirements, such as in public spaces, transportation, and protective clothing.

Upstream product

• 822-87-7 2-Chlorocyclohexanone 
• 122-52-1 triethyl phosphite 
• 1056477-06-5 2-bromocyclohexanone 
• 108-94-1 cyclohexanone 
• 814-49-3 diethyl chlorophosphate 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 
• 54058-00-3 diethyl phosphite potassium salt 

Downstream Products

• 78329-40-5 2-(cyclohex-1-en-1-yl)-1H-indole 
• 1821-23-4 1-cyclohex-1-enyl-4-methylbenzene 
• 134273-09-9 (E)-2-(3-phenylpropylidene)cyclohexanone 
• 108-94-1 cyclohexanone 
• 17497-53-9 1-iodo-1-cyclohexene 

Relevant academic research and scientific papers

The preparation of alkylaryldichlorocyclopropanol phosphates

In the present article we report the preparation of alkylaryldichlorocyclopropanol phosphates by the addition of dichlorocarbene to enol phosphates of propiophenone and cyclohexanone with steric hinderance. The stereoselectivity of enol phosphates and the effect of substituents on the carbene addition rate are discussed.

Stereoselective Csp3?Csp2 Cross-Couplings of Chiral Secondary Alkylzinc Reagents with Alkenyl and Aryl Halides

We report palladium-catalyzed cross-coupling reactions of chiral secondary non-stabilized dialkylzinc reagents, prepared from readily available chiral secondary alkyl iodides, with alkenyl and aryl halides. This method provides α-chiral alkenes and arenes with very high retention of configuration (dr up to 98:2) and satisfactory overall yields (up to 76 % for 3 reaction steps). The configurational stability of these chiral non-stabilized dialkylzinc reagents was determined and exceeded several hours at 25 °C. DFT calculations were performed to rationalize the stereoretention during the catalytic cycle. Furthermore, the cross-coupling reaction was applied in an efficient total synthesis of the sesquiterpenes (S)- and (R)-curcumene with control of the absolute stereochemistry.

Selective Alkenylation and Hydroalkenylation of Enol Phosphates through Direct C-H Functionalization

An efficient and selective Rh-catalyzed direct C-H functionalization reaction of enol phosphates was developed. The method is applicable to a variety of coupling partners, including activated alkenes, alkynes, and allenes, and leads to the formation of various valuable alkenylated and hydroalkenylated enol phosphates through the action of the phosphate directing group. The versatility and utility of the coupling products were demonstrated through further transformations into synthetically useful building blocks. P points the way: A direct C-H functionalization of enol phosphates was developed. The method is applicable to a variety of coupling partners, including activated alkenes, alkynes, and allenes, and it leads to the formation of alkenylated and hydroalkenylated enol phosphates through the action of the phosphate directing group. The utility of the coupling products are demonstrated by further transformations into synthetically useful building blocks.

Photostimulated reactions of vinyl phosphate esters with triorganostannides. Evidence for an SRN1 vinylic mechanism

Ketones are converted into vinyl diethyl phosphate esters (VinDEP), which under photostimulation reacted with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia affording vinylstannanes via a vinylic SRN1 mechanism.

The Reaction of Vinyl Phosphates with Iodotrimethylsilane: Synthesis of Vinyl Iodides from Ketones

A new method for preparation of vinyl iodides from ketones is described, based on the reaction of vinyl phosphates with iodotrimethylsilane.

Synthesis of β-Keto Phosphonates from Vinyl Phosphates via a 1,3-Phosphorus Migration

A new method for the preparation of β-keto phosphonates has been developed, involving rearrangement of vinyl phosphates upon treatment with strong base.Because this approach ultimately relies upon electrophilic dialkyl phosphorochloridates as the phosphor

Reaction of Triflates with Potassium Diethyl Phosphite. Formation of Phosphate Esters

Phenyl triflate and substituted analogues react with potassium diethyl phosphite in liquid ammonia to form aryl diethyl phosphate esters.The reaction formally involves loss of trifluoromethanesulfinate ion from the triflate and concomitant oxidation of phosphorus to the phosphate stage.Preliminary data suggest that, in a series of triflates, reactivity follows the order aryl > cyclohexenyl > cyclopropyl > alkyl.Studies on aryl triflates with added labeled phenoxide rule out a mechanism involving free phenoxide ion, i.e., displacement of phenoxide by nucleophilic attack of diethyl phosphite ion on sulfur followed by phosphorylation of displaced phenoxide.Three potential mechanisms, including one involving initial attack of phosphorus at sulfur, a biphilic insertion mechanism, and one involving nucleophilic attack on oxygen, are suggested, all of which could account for these observations.