66899-05-6

Upstream product

• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 41003-33-2 2-propenyloxydichlorophosphine 
• 591-87-7 Allyl acetate 
• 556-56-9 allyl iodid 

Downstream Products

• 874291-97-1 allylphosphinic acid benzyl ester 

Relevant academic research and scientific papers

Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols

A novel palladium-catalyzed allylation of H3PO2 with allylic alcohols is described. The phosphorus-carbon bond-forming reaction produces allylic-H-phosphinic acids and water, in the absence of additives. Primary H-phosphinic acids are obtained in excellent yields, whereas secondary H-phosphinic acids react sluggishly. A reusable polymer-supported catalyst is also described. The reaction provides an environmentally sound approach to H-phosphinic acids.

Palladium-catalyzed reactions of hypophosphorous compounds with allenes, dienes, and allylic electrophiles: Methodology for the synthesis of allylic H-phosphinates

(Chemical Equation Presented) Hypophosphorous compounds (MOP(O)H 2, M = H, R3NH) effectively participate in metal-catalyzed C-P bond-forming reactions with allenes, dienes, and activated allylic electrophiles under mild conditions. The catalytic system Pd2dba 3/xantphos is crucial to avoid or minimize the competitive reductive transfer-hydrogenation pathway available to hypophosphorous acid derivatives. Further investigation into the allylation mechanism provided access to the analogy allylic acetate - allylic phosphinate, which then led to the development of a Pd-catalyzed rearrangement of preformed allylic phosphinates esters and, ultimately, to a catalytic dehydrative allylation of hypophosphorous acid with allylic alcohols. The reactions disclosed herein constitute efficient synthetic approaches, not only to prepare allylic H-phosphinic acids but also their esters via one-pot tandem processes. In addition, the potential of H-phosphinates as useful synthons for the preparation of other organophosphorous compounds is demonstrated.

Design, synthesis, and biological evaluation of phosphinopeptides against Trypanosoma cruzi targeting trypanothione biosynthesis

As a part of our project aimed at the search for new safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas's disease); a series of phosphinopeptides structurally related to glutathione was designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible for this disease, the hemoflagellated protozoan Trypanosoma cruzi. The rationale for the synthesis of these compounds was supported on the basis that the presence of the phosphinic acid moiety would mimic the tetrahedral transition state of trypanothione synthase (TryS), a typical C:N ligase, and the molecular target of these drugs. Of the designed compounds, 53 and 54 were potent growth inhibitors against the clinically more relevant form of T. cruzi (amastigotes) growing in myoblasts. The efficacy for these drugs was comparable to that exhibited by the well-known antiparasitic agent WC-9. The simple phosphinopeptide structure found as a pharmacophore in the present study constitutes a starting point for the development of straightforward optimized drugs.

Synthesis of alkyl phosphinic acids from silyl phosphonites and alkyl halides

Mono- and di-substituted phosphinic acids have been synthesised in a one-pot reaction, by the addition of alkyl halides to silyl phosphonites, under mild and flexible conditions.

REACTION BETWEEN 2-HYDROXY ESTERS OF HYPOPHOSPHOROUS ACID AND ALCOHOLS

A study of the reaction between esters of hypophosphorous acid and alcohols is carried out.It has been established that the 2-hydroxy esters of hypophosphorous acid react with alcohols as a result of which phosphonous acids are formed.A possible scheme of this reaction is suggested.