4921-73-7

Basic information

• Product Name: diethyl sulfinylphosphoramidate
• CAS NO: 4921-73-7
• Molecular Formula: C₄H₁₀NO₄PS
• Molecular Weight: 199.1653
• Mol File: 4921-73-7.mol

Chemical Properties

• Boiling Point: 215.3°C at 760 mmHg
• Flash Point: 84°C
• Density: 1.39g/cm³
• Vapor Pressure: 0.218mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: diethyl sulfinylphosphoramidate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl sulfinylphosphoramidate(4921-73-7)
• EPA Substance Registry System: diethyl sulfinylphosphoramidate(4921-73-7)

Safety Data

• Hazardous Substances Data: 4921-73-7(Hazardous Substances Data)

Upstream product

• 1068-21-9 Diethyl phosphoramidate 
• 40923-48-6 diethyl N-(trimethylsilyl)phosphoroamidate 

Downstream Products

• 4921-77-1 (1-oxo-3-phenyl-3,6-dihydro-1H-1λ⁴-[1,2]thiazin-2-yl)-phosphonic acid diethyl ester 
• 40923-54-4 [(4-Chloro-phenyl)-(diethoxy-phosphorylamino)-methyl]-phosphoramidic acid diethyl ester 
• 40923-51-1 [(Diethoxy-phosphorylamino)-(2-nitro-phenyl)-methyl]-phosphoramidic acid diethyl ester 
• 1068-21-9 Diethyl phosphoramidate 
• 1159770-62-3 C₂₃H₂₄NO₃P 
• 1159770-59-8 C₁₀H₂₆N₂O₈P₂S 
• 22023-07-0 C₁₂H₃₀N₂O₈P₂S 
• 18856-89-8 diisopropyl N-sulfinylphosphoramidate 
• 33550-30-0 Triphenylarsin N-diethylphosphorimin 
• 40923-52-2 [(Diethoxy-phosphorylamino)-(3-nitro-phenyl)-methyl]-phosphoramidic acid diethyl ester 
• 40923-55-5 [(4-Chloro-3-nitro-phenyl)-(diethoxy-phosphorylamino)-methyl]-phosphoramidic acid diethyl ester 
• 40923-53-3 [(Diethoxy-phosphorylamino)-(4-nitro-phenyl)-methyl]-phosphoramidic acid diethyl ester 

Relevant articles and documents

New routes to diethyl 1-alkenylphosphoramidates

New routes to N-(diethoxyphosphoryl)imines derived from enolizable carbonyl compounds have been investigated. Three different procedures were studied: (i) the aza-Claisen condensation of ethyl-[N-(diethoxyphosphoryl)]-formimidate with enolizable ketones, (ii) the reaction between diethyl N-sulfinylphosphoramidate and aliphatic aldehydes, and (iii) the thermally induced reaction of diethyl phosphoramidate with ketone diethyl acetals. With two exceptions in all cases the products were identified as diethyl 1-alkenylphosphoramidates with no spectroscopically detectable amounts of imine tautomers. The aza-Claisen condensation can be recommended as a simple and effective route to diethyl 1-alkenyl-3-oxophosphoramidates. (C) 2000 Elsevier Science Ltd.

Synthesis of N,N'-Bis(diethylphosphoryl) Sulfamide

The reaction of phosphoroamidates 5a-c with an excess of sulfuryl chloride, as well as the reaction of 5a with sulfur trioxide were investigated. In both reactions, the formation of a new type of phosphoroorganic compound namely, N,N'-bis(diethylphosphoryl) sulfamide (6) was observed. This unexpected reaction pathway is rationalized as a result of the formation of dialkyl phosphorosulfonyl amide 3, a reactive common intermediate in both processes.

Reactivity and diastereoselectivity in the thermal and Lewis acid- catalyzed Diels-Alder reactions of N-sulfinylphosphoramidates

The [4 + 2] cycloaddition reactions of N-sulfinylphosphoromidates, prepared from the corresponding phosphoramidates by treatment with N- (chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10) and presence (> 95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as Well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.

SYNTHESIS OF N-PHOSPHORYLATED SULPHINYL COMPOUNDS AND REACTIONS WITH VARIOUS DIENES

It is reported about the synthesis and doubtless identification of the title compounds, including some cycloaddition reactions.