171503-16-5

Upstream product

• 130517-96-3 N-(4-chlorobenzylidene)benzylamine 
• 868-85-9 Dimethyl phosphite 
• 100-46-9 benzylamine 
• 104-88-1 4-chlorobenzaldehyde 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 171503-03-0 (C₆H₅)3GeCH₂CH₂C(O)N(CH₂C₆H₅)(CHC₆H₄Cl)(P(O)(OCH₃)2) 

Relevant academic research and scientific papers

Synthesis of α-aminophosphonates in the presence of triethylammonium hydrogen sulfate [Et3NH][HSO4] as a highly efficient ionic liquid catalyst

Triethylammonium hydrogen sulfate was used as a cheap and mild acidic ionic liquid for efficient, one-pot, three-component reaction of aldehydes, amines and trimethyl phosphite. Thus α-aminophosphonates were synthesized at room temperature in excellent yields. The ionic liquid catalyst is air and water stable, easy to prepare from amine and acid and easily separated from the reaction mixture. (Chemical Equation Presented).

Phenylphosphonic acid as efficient and recyclable catalyst in the synthesis of α-aminophosphonates under solvent-free conditions

Phenylphosphonic acid is an efficient, friendly and reusable heterogeneous catalyst for the synthesis of α-aminophosphonates through a 'one-pot' three-component reaction of amines, carbonyl compounds and dialkyl phosphites under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines, aliphatic and aromatic aldehydes and aliphatic ketones. It also enabled the synthesis of α-aminophosphonates in large scale, clean conversion, easy workup and purification. Excellent results were obtained in each case obtaining the desire compounds in moderate to good yields. Georg Thieme Verlag Stuttgart New York.

Phenylboronic acid as efficient and eco-friendly catalyst for the one-pot, three-component synthesis of α-aminophosphonates under solvent-free conditions

A simple, mild, and efficient one-pot, three-component synthetic method has been developed for the preparation of α-aminophosphonates using phenylboronic acid as catalyst under solvent-free conditions at 50°C. The process involves the reaction of carbonyl compounds (aldehydes or ketones) with benzylamine and dimethyl phosphite. A wide range of carbonyl compounds are compatible with this reaction, producing tertiary and quaternary α-aminophosphonates in moderated to excellent yields in short time. Georg Thieme Verlag Stuttgart · New York.

Cobalt(II) chloride accelerated one-pot three-component synthesis of α-aminophosphonates at room temperature

A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of α-aminophosphonates from condensation reaction of trimethyl phosphite, aryl aldehydes and aryl amines in the presence of CoCl2·6H2O under solvent-free conditions. Thus α-aminophosphonates were synthesized relatively quickly in good yields at room temperature.

Organocatalytic synthesis of α-hydroxy and α-aminophosphonates

A new and highly flexible procedure is described for the synthesis of α-amino- and α-hydroxy phosphonates. In the presence of a catalytic amount of oxalic acid (10 mol %), trimethyl phosphite reacts with aldehydes or imines (generated in situ from an aldehyde and an amine) to yield the corresponding coupled products in good yield.

Dimethyl phosphonate

The title compound, C16H19ClNO3P, is one of a series of α-substituted aminomethyl phosphonates.There are two independent molecules in the asymmetric unit and it each the P atom adopts a tetrahedral configuration.The P=O double-bond length and the mean P-O single-bond length are 1.425(5) and 1.560(5) Angstroem for molecule (1) and 1.417(6) and 1.562(5) Angstroem for molecule (2), respectively.The P=O double-bond lengths in both molecules are shorter than those in 1,3,2-oxazaphospholidine derivatives and caged bicyclic phosphorus compounds.

SYNTHESIS AND ANTITUMOR ACTIVITY OF NOVEL &α-SUBSTITUTED AMINOMETHYLPHOSPHONATES

Two series of novel α-substituted aminomethyl phosphonates (1) and (2) have been synthesized and the reaction conditions are discussed.All the products have been confirmed by 1H NMR, IR spectra and elemental analysis, and x-ray diffraction.The bioassay showed that some of the compounds inhibit the growth of the leukemia L1210 cell in vitro.Key words: Aminomethylphosphonate; synthesis; antitumor activity; X-ray diffraction.