26386-88-9 Usage
Chemical Properties
Diphenylphosphoryl azide (DPPA) is a colorless or pale yellow liquid which boils at 134-136 °C/0.2 mmHg, and it will be stable at room temperature under shading. It is non-explosive just like the other phosphorazidate. When DPPA is stored at room temperature for a long time, it might be slowly and partially hydrolyzed with moisture in air to produce diphenyl phosphate and toxic explosive hydrazoic acid. In this case, it will be recommended to use after washing DPPA with aqueous sodium hydrogen carbonate followed by drying.
Uses
Diphenylphosphoryl azide (DPPA or diphenyl phosphorazidate, (PhO)2P(O)N3) is a very toxic and potentially explosive organic compound. DPPA has been found to be effective for a variety of organic reactions as a versatile synthetic reagent. It is widely used in synthesis of other organic compounds especially as a reagent for the synthesis of peptides by virtue of its reactions with carboxylic acids leading to either the urethane or the amide.
Application
Diphenylphosphoryl azide (DPPA) is a well-known azide reagent used in peptide couplings, Curtius rearrangements, and Mitsunobu inversions—is often encountered in pharmaceutical process development because it enables the most direct route to a desired product. Diphenylphosphonic azide acts as a reagent for the synthesis of peptides and phosphoramidates by reacting with amines. It is also used in the preparation of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement. It is involved in pseudohalogen replacement of the azido group by treatment with nucleophilic reagents, such as water, butanol, ammonia, and various amines. Further, it is used as a hydroazidation catalyst for preparation of organoazides.
Preparation
Diphenylphosphoryl azide (DPPA) is easily prepared in high yield by the reaction of the corresponding chloride with sodium azide in acetone. Combination of sodium azide and 18-crown-6 in the same reaction was reported, and the use of a quaternary ammonium salt as a phase-transfer catalyst in a biphasic phase of water and an organic solvent was also reported to be effective, as shown in Scheme 3.Diphenyl Phosphorazidate (DPPA) - More Than Three Decades LaterTakayuki ShioiriGraduate School of Environmental and Human Sciences, Meijo University
Reactions
Diphenylphosphoryl azide, originally developed by Yamada in 1972, has shown significant synthetic versatility, being used in isocyanate synthesis, especially in the Curtius rearrangement, stereospecific conversion of alcohol into azide, as a coupling reagent in macrolactamization[4], in allylic amine synthesis, and in aziridination reactions. Diphenylphosphoryl azide, also called DPPA, diphenyl phosphorazidate or phosphoric acid diphenyl ester azide, is a colorless liquid with high boiling point (157 °C/0.17 mmHg), and can be easily prepared by the reaction between diphenylphosphoryl chloride and sodium azide in acetone in high yield. The Waldvogel group developed a reliable protocol for the large-scale (100 g) synthesis of DPPA, including purification by reduced-pressure distillation (Picture 1). A polymer-supported form of the reagent has also been developed using phenol resin by the Taylor group.
Check Digit Verification of cas no
The CAS Registry Mumber 26386-88-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,3,8 and 6 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 26386-88:
(7*2)+(6*6)+(5*3)+(4*8)+(3*6)+(2*8)+(1*8)=139
139 % 10 = 9
So 26386-88-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H10N3OP/c13-14-15-17(16,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
26386-88-9Relevant articles and documents
Phase-transfer catalyzed pseudohalogenation of phosphorochloridates
Shi, Enxue,Pei, Chengxin
, p. 669 - 673 (2005)
Pseudohalogenation of phosphorochloridates by sodium pseudohalides with different phase transfer catalysts and solvents was optimized. Dialkyl and diaryl phosphorazidates phosphorocyanidates, and phosphor(isotniocyanidate)s were prepared in good yields from phosphorochloridates under two kinds of mild phase-transfer catalyzed conditions respectively.
Zinc-catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides
Ying, Jun,Gao, Qian,Wu, Xiao-Feng
supporting information, p. 1540 - 1543 (2020/04/15)
We have developed a facile and efficient procedure for the synthesis of diarylphosphate esters and amides. Using Zn(acac)2 as the catalyst, the reaction of diarylphosphoryl azides with aliphatic alcohols and phenols through an unusual P?N bond cleavage provided a number of diarylphosphate esters in good yields (22 examples, up to 94%). Additionally, various diarylphosphate amides were obtained from the corresponding amines in excellent yields as well (8 examples, up to 96%).
Palladium-Catalyzed One-Pot Synthesis of N -Sulfonyl, N -Phosphoryl, and N -Acyl Guanidines
Qiao, Guanyu,Zhang, Zhen,Huang, Baoliang,Zhu, Liu,Xiao, Fan,Zhang, Zhenhua
supporting information, p. 330 - 340 (2018/01/12)
An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N -sulfonyl-, N -phosphoryl-, and N -acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.
Preparation method and application of 1,2,3-triazole diphenyl phosphate inulin derivative
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Paragraph 0029, (2018/11/03)
The invention relates to the fields of food, medical treatment and cosmetics, specifically to a preparation method and application of a 1,2,3-triazole diphenyl phosphate inulin derivative. the preparation method comprises the following steps: firstly usin
