52956-34-0

Upstream product

• 67-56-1 methanol 
• 31430-66-7 2-propyl phosphorodichloridite 
• 868-85-9 Dimethyl phosphite 
• 67-63-0 isopropyl alcohol 
• 122194-07-4 dimethyl N,N-diisopropylphosphoramidite 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 690-64-2 isopropyl methyl methylphosphonate 
• 756-79-6 dimethyl methane phosphonate 
• 1231709-89-9 C₂₆H₂₇N₂O₇P 
• 1231710-03-4 C₂₈H₃₁N₂O₇P 

Relevant academic research and scientific papers

Bisphosphonic compounds. II. Preparation of monophosphonic starting materials. Mixed esters of methylphosphonic acid

Methyl (1-methylethyl) methylphosphonate was obtained from PCl3 via (Pr(i)O)PCl2 and (Pr(i)O)P(OMe)2 followed by the Michaelis-Arbuzov reaction with Mel. The yield was 79% with 95% chemical purity. Less reasonable conversions were obtained for some related mixed diesters.

Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites

Unsymmetrical phosphites react efficiently in a Staudinger reaction with p-azido-phenylalanine, which can be applied for the biotinylation of proteins, thereby expanding the scope of the chemoselective Staudinger-phosphite reaction of aryl azides with symmetrical phosphites to the corresponding phosphoramidates. The Royal Society of Chemistry 2010.

Organophosphorus chemistry. Part 1: The synthesis of alkyl methylphosphonic acids

Several alkyl hydrogen methylphosphonates of structure RO(HO)P(O)Me were synthesised by a three-stage route [R =i-Pr, n-Bu, i-Bu, s-Bu, pinacolyl Me3C-CH(Me)-, cyclopentyl and cyclohexyl]. Trimethyl phosphite was transesterified with alcohols in the presence of sodium catalyst to give the mixed phosphites (MeO)2POR in 6-64% yield. Treatment of these with methyl iodide gave alkyl methyl methylphosphonates RO(MeO)P(O)Me in 66-95% yield. Selective demethylation of these compounds by bromotrimethylsilane, followed by methanolysis of the phosphorus silyl esters RO(Me3SiO)P(O)Me, gave the hydrogen phosphonates in 60-97% yield.

Phosphitylation via the Mitsunobu reaction

Treatment of a dialkyl phosphite with triphenylphosphine and diisopropyl azodicarboxylate in toluene, followed by addition of an alcohol, results in the formation of the corresponding trialkyl phosphite. Similarly, dialkyl phosphonites can be synthesised from monoalkyl phosphites (alkyl phosphinates).