28519-15-5

Upstream product

• 107-66-4 dibutyl phosphate 
• 108-88-3 toluene 
• 100-51-6 benzyl alcohol 
• 819-43-2 dibutyl chlorophosphate 
• 100-39-0 benzyl bromide 
• 1809-19-4 dibutyl hydrogen phosphite 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Cetyltrimethyl ammonium bromide catalysed oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds

An efficient metal-free method for the synthesis of organophosphorus compounds via oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds catalysed by cetyltrimethyl ammonium bromide (CTAB) is

Synthesis, biochemical evaluation, and molecular modeling studies of aryl and arylalkyl di-n-butyl phosphates, effective butyrylcholinesterase inhibitors

A series of dialkyl aryl phosphates and dialkyl arylalkyl phosphates were synthesized. Their inhibitory activities were evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The di-n-butyl phosphate series consistently displayed selective inhibition of BChE over AChE. The most potent inhibitors of butyrylcholinesterase were di-n-butyl-3,5-dimethylphenyl phosphate (4b) [KI?=?1.0?±?0.4?μM] and di-n-butyl 2-naphthyl phosphate (5b) [KI?=?1.9?±?0.4?μM]. Molecular modeling was used to uncover three subsites within the active site gorge that accommodate the three substituents attached to the phosphate group. Phosphates 4b and 5b were found to bind to these three subsites in analogous fashion with the aromatic groups in both analogs being accommodated by the “lower region,” while the lone pairs on the P[dbnd]O oxygen atoms were oriented towards the oxyanion hole. In contrast, di-n-butyl-3,4-dimethylphenyl phosphate (4a) [KI?=?9?±?1?μM], an isomer of 4b, was found to orient its aromatic group in the “upper left region” subsite as placement of this group in the “lower region” resulted in significant steric hindrance by a ridge-like region in this subsite. Future studies will be designed to exploit these features in an effort to develop inhibitors of higher inhibitory strength against butyrylcholinesterase.

Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides

A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.

Tetrabutylammonium iodide-catalyzed phosphorylation of benzyl c-h bonds via a cross-dehydrogenative coupling (cdc) reaction

Phosphate esters play important roles as biological active principles and synthons in chemistry. An efficient metal-free approach for the synthesis of phosphate esters through sp3 C-H activation is described. By using tetrabutylammonium iodide (Bu4NI) as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant, various toluene derivatives and phosphorus nucleophiles are tolerated in this transformation, affording the corresponding products in moderate to good yields.