1498-65-3

Basic information

• Product Name: dimethylphosphoramidothioic dichloride
• Synonyms: Phosphoramidothioic dichloride, dimethyl-
• CAS NO: 1498-65-3
• Molecular Formula: C₂H₆Cl₂NPS
• Molecular Weight: 178.0205
• Mol File: 1498-65-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 182.4°C at 760 mmHg
• Flash Point: 64.1°C
• Density: 1.44g/cm³
• Vapor Pressure: 0.81mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: dimethylphosphoramidothioic dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: dimethylphosphoramidothioic dichloride(1498-65-3)
• EPA Substance Registry System: dimethylphosphoramidothioic dichloride(1498-65-3)

Safety Data

• Hazardous Substances Data: 1498-65-3(Hazardous Substances Data)

Upstream product

• 683-85-2 N,N-dimethylaminodichlorophosphane 
• 506-59-2 N,N-dimethylammonium chloride 
• 71-55-6 1,1,1-trichloroethane 
• 124-40-3 dimethyl amine 
• 677-43-0 N,N-dimethylphosphoroamidic dichloride 

Downstream Products

• 28167-51-3 N,N-dimethyl O,O-dimethyl phosphoramidothioate 
• 95980-94-2 dimethyl-amidothiophosphoric acid O-ethyl ester-O'-(4-chloro-phenyl ester) 
• 94406-57-2 dimethyl-amidothiophosphoric acid O-ethyl ester-O'-(2,4,5-trichloro-phenyl ester) 
• 100869-48-5 dimethyl-amidothiophosphoric acid O,O'-bis-(4-chloro-phenyl ester) 
• 57858-66-9 N,N-dimethyl-N',N''-diphenyl-thiophosphamide 
• 812-13-5 Difluorthiophosphorsaeure-dimethylamid 
• 1778-99-0 Thiophosphorsaeure-O,O-bis-pentachlorphenylester-dimethylamid 
• 81581-16-0 (2R,4R,5S)-2-dimethylamino-4-methyl-5-phenyl-1,3,2-oxazaphospholidine-2-thione 

Relevant articles and documents

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Linear synthesis of chiral cycloSal-pronucleotides

CycloSal-nucleosyl-phosphate triesters are a known class of highly effective nucleotide prodrugs (pronucleotides) of antivirally active nucleoside analogues. Until recently, the synthesis of these compounds always gave diastereoisomeric mixtures. Then, a convergent route for the stereospecific synthesis of cycloSal-triesters was described to give isomerically pure cycloSal-prodrugs for the treatment of viral diseases. Here, the development of a stereoselective synthesis of these pronucleotides using various chiral auxiliaries is described. In contrast to pyrrolidine- or pyrrolidinone derivatives it was found that a thiazolidine derived from valinol fulfilled all three requirements to act as a suitable chiral moiety, allowing: (i) strong chirality transfer, (ii) the formation of separable diastereoisomeric intermediates, and (iii) a suitable leaving group that allows the introduction of the nucleoside analogue (e.g., d4T) in the final step under mild reaction conditions. The title compounds were obtained with very high diastereoisomeric excesses of more than 95%. The development of a stereoselective route to cycloSal-nucleotides of thymidine and d4T based on the use of various chiral auxiliaries is reported. The target chiralphosphates were obtained with very high diastereoisomeric excesses of more than 95%.

Thionation of phosphoramidodichloridates and phosphoramidate diesters using phosphorus pentasulfide and hexamethyldisiloxane under microwave irradiation. Part 1

A new, mild, efficient, and solvent-free microwave promoted synthesis of thiophosphoramidodichloridates and thiophosphoramidate diesters is described. The thionation reaction was accelerated with microwave irradiation using the combination of P4S10 and HMDO. The conversion of PO to PS by this method gave the desired product in higher yields and shorter reaction times as compared to conventional methods.