22685-20-7

Basic information

• Product Name: DIETHYL TERT-BUTYL AMIDOPHOSPHATE
• Synonyms: DIETHYL TERT-BUTYL AMIDOPHOSPHATE;DIETHYL TERT-BUTYL PHOSPHORAMIDATE
• CAS NO: 22685-20-7
• Molecular Formula: C₈H₂₀NO₃P
• Molecular Weight: 209.22
• Mol File: 22685-20-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 233.8°Cat760mmHg
• Flash Point: 95.2°C
• Appearance: /
• Density: 1.014g/cm³
• Vapor Pressure: 0.0547mmHg at 25°C
• Refractive Index: 1.427
• CAS DataBase Reference: DIETHYL TERT-BUTYL AMIDOPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL TERT-BUTYL AMIDOPHOSPHATE(22685-20-7)
• EPA Substance Registry System: DIETHYL TERT-BUTYL AMIDOPHOSPHATE(22685-20-7)

Safety Data

• Hazardous Substances Data: 22685-20-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 6513, 1987 DOI: 10.1016/S0040-4039(00)96903-X

InChI:InChI=1/C8H20NO3P/c1-6-11-13(10,12-7-2)9-8(3,4)5/h6-7H2,1-5H3,(H,9,10)

Upstream product

• 75-64-9 tert-butylamine 
• 762-04-9 phosphonic acid diethyl ester 
• 95-31-8 N-(tert-butyl)benzothiazole-2-sulfenamide 
• 762-04-9 Diethyl phosphonate 
• 814-49-3 diethyl chlorophosphate 
• 118132-81-3 tert-Butyl-phosphorimidic acid triethyl ester 

Relevant articles and documents

Organophotocatalytic Synthesis of Phosphoramidates

We describe the use of visible light in conjunction with an organic dye for the synthesis of phosphoramidates. Cross dehydrogenative coupling reactions between phosphites and amines are reported using organic dyes and light as catalysts for the first time. It is not only a novel application of organic dyes but also fulfils the requirement of sustainability and green chemistry avoiding the use of chromatographic purification techniques. The product was simply isolated from the reaction mixture via an acid-base work-up procedure, rendering the pure product in good yields.

Phosphoramidate-mediated conversion of carbonyl ligands into isocyanide ligands: A new approach to chiral isocyanide ligands

Metal isocyanides have been used and studied by organometallic chemists for many years and, as a result, they have a rich and interesting chemistry. The nature of metal-free isocyanides and the methods of making isocyanide complexes, however, has resulted

Evidence for Cyclic Azaphosphiridine Oxide Intermediates in the Methoxide-induced Rearrangements of N-Alkyl α-Chlorophosphonamidates: Formation of Phosphoramidates as well as α-Aminophosphonates

The N-butyl α-chlorophosphonamidates RCHClP(O)(NBut)OMe (R=H, Me, or Ph) react with benzyltrimethylammonium methoxide in tetrahydrofuran-methanol to give two types of rearrangement product, the α-aminophosphonates ButNHCHRP(O)(OMe)2 and the phosphoramidates But(RCH2)NP(O)(OMe)2.For the phosphoramidates it seems necessary to postulate the formation of a cyclic azaphosphiridine oxide intermediate, and its subsequent ring-opening, by nucleophilic attack of methoxide at phosphorus, with cleavage of the P-C bond.The α-aminophosphonates are probably also derived from the azaphosphiridine oxide, by cleavage of the P-N bond.The observation that the proportion of the phosphoramidate (P-C cleavage) increases as R changes from Me to H to Ph accords with this picture, as does the apparent lack of any P-C bond cleavage in the rearrangement of Me2CClP(O)(NHR')OMe (R'=Me or But).