813-77-4

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl phosphorochloridate is used as a reagent for the preparation of (E)-3-cyanophosphoenolpyruvate, which is an important intermediate in the synthesis of pharmaceutical compounds. It is prepared by reacting dimethyl phosphorochloridate with the potassium enolate of ethyl cyanopyruvate.
Used in Organic Synthesis:
Dimethyl phosphorochloridate is used as a reagent for the synthesis of monoand diphosphate esters of 2-arachidonyl glyceryl ether. These esters have potential applications in various fields, including medicine and biochemistry.

Synthesis Reference(s)

Canadian Journal of Chemistry, 34, p. 1819, 1956 DOI: 10.1139/v56-235Synthetic Communications, 23, p. 1771, 1993 DOI: 10.1080/00397919308011275

InChI:InChI=1/C2H6ClO3P/c1-5-7(3,4)6-2/h1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 96-36-6 methyl phosphite 
• 594-42-3 chlorothio-trichloro-methane 
• 75-44-5 phosgene 
• 121-45-9 phosphorous acid trimethyl ester 
• 7782-50-5 chlorine 
• 36198-87-5 dimethyl trimethylsilyl phosphite 
• 545-06-2 trichloroacetonitrile 
• 121-44-8 triethylamine 
• 473-29-0 N,N-Dichlorobenzenesulfonamide 
• 128-09-6 N-chloro-succinimide 

Downstream Products

• 6161-79-1 denitrofenitrooxon 
• 4143-37-7 S-(4-methylphenyl) O,O'-dimethyl phosphorothiolate 
• 3820-53-9 S-(4-nitrophenyl) O,O'-dimethyl phosphorothiolate 
• 20464-99-7 dimethyl-N-ethylphosphoramidate 
• 20465-00-3 N-Propyl-O,O-dimethyl-phosphorsaeureamid 
• 68204-27-3 dimethyl (4-phenylbuta-2,3-dien-2-yl)phosphonate 
• 16115-01-8 α--α--toluol 
• 4532-05-2 Phosphorsaeure-- 
• 38289-86-0 (E)-3-(Dimethoxy-phosphoryloxy)-2-methyl-acrylic acid 1-phenyl-ethyl ester 
• 37141-75-6 C₁₀H₁₄NO₅P 
• 70636-23-6 C₁₂H₂₁NO₇P₂ 
• 30574-75-5 C₁₀H₁₄BrN₂O₅P 
• 30574-60-8 C₁₁H₁₆ClN₂O₆P 
• 597-23-9 Pyrophosphorsaeure-trimethylester-diethylamid 

Relevant academic research and scientific papers

Development of a second generation coenzyme a analogue synthon

We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) which involves enzymatic synthesis of a general CoA analogue synthon having a thioester linkage in place of the amide bond nearest the thiol group (Martin et al. J. Am. Chem. Soc. 1994, 116, 4660). We report here the synthesis of a second CoA analogue synthon 1c which has the amide bond more distant from the thiol group replaced with a thioester. This analogue was prepared by nonenzymatic synthesis of a racemic phosphopantetheine analogue followed by enzymatic conversion to the corresponding CoA analogue. Stereochemical analysis showed that the natural enantiomer of the phosphopantetheine analogue was selectively converted to product by the enzyme phosphopantetheine adenylyltansferase, yielding a product that possessed the desired stereoconfiguration. Reaction of the new synthon 1c with a primary amine results in amide bond formation to form the CoA analogue of interest. This new methodology provides access to an even broader array of CoA analogues modified in the β-alanylcysteamine moiety. This has been demonstrated in the synthesis of an analogue having an extra methylene group in the β-alanine moiety and two analogues in which the amide bond nearest the thiol group is replaced with a pair of methylene groups.

PHOSPHONATE DERIVATIVES OF LIPOPHILIC AMINES

This invention relates to a class of novel phosphonate derivatives of lipophilic amines which exhibit squalene synthase inhibition properties. More specifically the compounds are bis aryl cycloalkylamino and azacycloalkyl phosphonates. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.

Tellurium tetrachloride as an efficient chlorinating agent for di- or trialkyl phosphites: Novel synthesis of dialkyl chlorophosphates

Various dialkyl chlorophosphates are prepared by the reaction of TeCl4 with di- or trialkyl phosphites in good yields.

Effective Charge Distribution for Attack of Phenoxide Ion on Aryl Methyl Phosphate Monoanion: Studies Related to the Action of Ribonuclease

The reaction of phenoxide ion with aryl methyl phosphate monoanions and aryl diethyl phosphates obeys second-order kinetics in aqueous solution at 39 deg C and 1 M ionic strength.The second-order rate constants (M-1s-1) for these reaction obey the following Broensted equations: log k2 = -0.51pKlg + 0.72 (r = 0.970) (aryl diethyl phosphate) log k2 = -0.64pKlg - 2.53 (r = 0.898) (aryl methyl phosphate monoanion) The monoanion is some 104-fold less reactive toward attack by phenolate ion than is the diethyl ester with 4-nitrophenol leaving group, consistent in part with the operation of an electrostatic effect.The similarity between the Broensted exponents in both reactions indicates that the effective charge change on the leaving oxygen from ground state to transition state is similar in both cases; this indicates that the oxyanion in the monoanion case does not assist leaving group expulsion.The date are consistent with little coupling between proton abstraction from the 2'-hydroxyl group and the leaving group expulsion in the ribonuclease reaction.

REACTIONS OF PHOSPHITES WITH TRICHLOROACETONITRILE

Dialkyl hydrogen, sodium dialkyl, and dialkyl silyl phosphites react with trichloroacetonitrile by the Atherton-Todd scheme.Trialkyl phosphites add at the C(*)N bond of trichloroacetonitrile with the formation of trialkyl phosphorimidates.