20345-62-4

Usage

Uses

Used in Flame Retardant Industry:
TRIETHYL 4-PHOSPHONOCROTONATEDISC 6/01 is used as a flame retardant additive for enhancing the fire resistance of various materials. The phosphorus atom in its structure contributes to its effectiveness in this application by potentially forming phosphoric acid derivatives that can slow down the combustion process.
Used in Chemical Synthesis:
TRIETHYL 4-PHOSPHONOCROTONATEDISC 6/01 is used as a reagent or intermediate in the synthesis of other phosphorus-containing compounds. Its crotonate functional group allows for reactivity with other organic compounds, making it a valuable component in the production of phosphoric acid derivatives and other related chemicals.
Used in Industrial Chemistry:
TRIETHYL 4-PHOSPHONOCROTONATEDISC 6/01 is used as a component in various industrial chemical processes. Its unique structure and reactivity with other compounds make it a promising candidate for use in the development of new materials and products in the chemical industry.

InChI:InChI=1/C10H19O5P/c1-5-9(10(11)13-6-2)16(12,14-7-3)15-8-4/h5H,6-8H2,1-4H3/b9-5-

Upstream product

• 17145-91-4 triethyl 2-ethylphosphonoacetate 

Downstream Products

• 87088-38-8 4-Cyclohex-1-enyl-2-(diethoxy-phosphoryl)-3-methyl-butyric acid ethyl ester 

Relevant academic research and scientific papers

Investigation on lewis acid mediated diels-alder reactions of 2-phosphono-2-alkenoates. Application to total synthesis of (±)-α- alasken-8-one via reductive alkylation of resulting adduct

(Chemical Equation Presented) The Lewis acid mediated Diels-Alder reactions of three 2-phosphono-2-alkenoates including triethyl 2-phosphonoacrylate (1), triethyl 2-phosphonobut-2-enoate (2), and ethyl 2-(diethoxyphosphono)-3- methylbut-2-enoate (3) have been investigated. Of several Lewis acids tested, tin(IV) chloride was shown to be the most effective at enhancing the regio- and stereoselectivity of the reactions of 1 with the electron-rich dienes to result in the formation of the single regio- and/or stereoisomers in good yields. Bearing the β methyl group(s), 2 displayedmuch less reactivity than 1 while 3 was completely unreactive under the study's conditions. Throughout the investigation, we found that the cycloadditions of 2, especially of the Z-isomer, could be efficiently induced by using zinc chloride at elevated temperatures. Furthermore, a lithium naphthalenide (LN)-induced reductive alkylation process was applied to the resulting Diels-Alder adducts 4 to allow the phosphono group at the quaternary carbon centers to be replaced by various alkyl groups to afford the alkyl-substituted esters 12, therefore practically turning 1 and 2 into the useful synthetic equivalents of the corresponding 2-alkyl 2-alkenoates that usually display poor Diels-Alder reactivity. Application of this combined operation has facilitated the total synthesis of the sesquiterpene natural product α-alasken-8-one (8) in racemic form.