6833-67-6

Usage

Synonyms

Allylphosphonic acid, 2-propenylphosphonic acid

Physical State

Clear, colorless liquid

Odor

Strong odor

Solubility

Soluble in water

Main Use

Chelating agent

Industrial Applications

Metal surface treatment
Water treatment
Oilfield applications

Raw Material for Synthesis

Various phosphonates
Other phosphorus-based compounds

Thermal Stability

Excellent

Chemical Compatibility

High compatibility with a wide range of other chemicals

Allylphosphonic acid is valued for its versatility and usefulness across multiple industrial sectors due to its properties like solubility, thermal stability, and compatibility with other chemicals.

Upstream product

• 128176-61-4 bis(4-methoxyphenyl) allylphosphonate 
• 757-54-0 allylphosphonic acid dimethyl ester 
• 1067-87-4 Diethyl allylphosphonate 

Downstream Products

• 187737-37-7 propene 

Relevant academic research and scientific papers

Ring closing metathesis reactions on a phosphonate template

The first examples of ring-closing metathesis reactions on a phosphonate template catalyzed by the ruthenium alkylidene 3 are described. The yield, rate, and mode of cyclization in these reactions are sensitive to simple olefin substitution. The highlight of this method is the efficient syntheses of 2-alkyloxy-3,6-dihydro-[1,2]oxaphosphinine 2-oxide heterocycles (2).

Wet and dry processes for the selective transformation of phosphonates to phosphonic acids catalyzed by br?nsted acids

A "wet"process and two "dry"processes for converting phosphonate esters to phosphonic acids catalyzed by a Bronsted acid have been developed. Thus, in the presence of water, a range of alkyl-, alkenyl-, and aryl-substituted phosphonates can be generally hydrolyzed to the corresponding phosphonic acids in good yields catalyzed by trifluoromethyl sulfonic acid (TfOH) at 140 °C (the wet process). On the other hand, with specific substituents of the phosphonate esters, the conversion to the corresponding phosphonic acids can be achieved under milder conditions in the absence of water (the dry process). Thus, the conversion of dibenzyl phosphonates to the corresponding phosphonic acids took place smoothly at 80 °C in toluene or benzene in high yields. Moreover, selective conversion of benzyl phosphonates RP(O)(OR′)(OBn) to the corresponding mono phosphonic acids RP(O)(OR′)(OH) can also be achieved under the reaction conditions. The dealkylation via the generation of isobutene of ditert- butyl phosphonate, and the related catalysis by TfOH took place even at room temperature to give the corresponding phosphonic acids in good to high yields. Nafion also shows high catalytic activity for these reactions. By using Nafion as the catalyst, phosphonic acids could be easily prepared on a large scale via a simple process.

Amino acid based prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents

Fosmidomycin is a natural antibiotic with promising IspC (DXR, 1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitory activity. This enzyme catalyzes the first committed step of the non-mevalonate isoprenoid biosynthesis pathway, which is essential i

Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents

Two classes of prodrugs of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. To this end, a novel efficient synthesis route was developed involving a cross metathe

Zwitterionic pyrrolidene-phosphonates: Inhibitors of the glycoside hydrolase-like phosphorylase: Streptomyces coelicolor GlgEI-V279S

We synthesized and evaluated new zwitterionic inhibitors against glycoside hydrolase-like phosphorylase Streptomyces coelicolor (Sco) GlgEI-V279S which plays a role in α-glucan biosynthesis. Sco GlgEI-V279S serves as a model enzyme for validated anti-Tuberculosis (TB) target Mycobacterium tuberculosis (Mtb) GlgE. Pyrrolidine inhibitors 5 and 6 were designed based on transition state considerations and incorporate a phosphonate on the pyrrolidine moiety to expand the interaction network between the inhibitor and the enzyme active site. Compounds 5 and 6 inhibited Sco GlgEI-V279S with Ki = 45 ± 4 μM and 95 ± 16 μM, respectively, and crystal structures of Sco GlgE-V279S-5 and Sco GlgE-V279S-6 were obtained at a 3.2 ? and 2.5 ? resolution, respectively.

Remote supramolecular control of catalyst selectivity in the hydroformylation of alkenes

In the pocket: The supramolecular interactions between a Rh phosphine catalyst equipped with an anion-binding pocket and alkenes that contain anionic functionalities (see picture) provide an excellent design concept to achieve remote control of the regioselectivity in hydroformylation reactions. The 4-pentenoate and 3-butenylphosphonate, which fit tightly between the Rh center and the pocket, were hydroformylated with unprecedented selectivity.

Asymmetric synthesis of phosphonic acid analogues for acylcarnitine

Phosphonic acid analogues of acylcarnitine were prepared in an optically active form expecting CPT I inhibitory activities. The synthetic methodology was based on catalytic asymmetric dihydroxylation of β,γ-unsaturated phosphonates and subsequent regiosel

Phosphonates useful as modulators of t γ(g)9γ(d)2 lymphocyte activity

The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T γ9δ2 lymphocyte activity and pharmaceutical compositions comprising them.

Synthesis of prenyl pyrophosphonates as new potent phosphoantigens inducing selective activation of human Vγ9Vδ2 T lymphocytes

γ9δ2T cells represent the most abundant population of human blood γδT lymphocytes. They produce and promote strong cytotoxic activity against many pathogens that are implicated in several human infectious diseases. Their activation requires their exposure to small phosphorus- containing antigens in the family of prenyl pyrophosphates and their related biosynthetic precursors such as isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are naturally occurring metabolites in mycobacteria and several other microbial pathogens. The broad specificity in the recognition of these molecules by the T-lymphocyte population expressing a Vγ9Vδ2 cell receptor might facilitate their manipulation by designing small potent synthetic agonist ligands. In this paper, we describe the synthesis and the biological evaluation of new pyrophosphonate compounds as new isosteric analogues of natural prenyl pyrophosphates. Several prenyl and alkenyl pyrophosphonate with different chain lengths and degrees of insaturation (24-28, 48-50, and 64-66) were tested as well as the alkoxymethylpyrophosphonic analogue of IPP (compound 76) as its closest isostere. Several of them appeared to be better activators of Vγ9Vδ2 T cell proliferation than IPP. These results open the perspective of a potential use of isoprenoides pyrophosphonates as specific immunoregulatory molecules.

Synthesis of chiral γ-amino-β-hydroxyphosphonate derivatives from unsaturated phosphonates

γ-Amino-β-hydroxyphosphonates, useful intermediates for the synthesis of phosphonic acid analogues of carnitine, were prepared as their protected derivatives in an enantioselective manner from β,γ- unsaturated phosphonates through asymmetric dihydroxylati