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Diphenylphosphoryl azide

CAS No.
26386-88-9
Chemical Name:
Diphenylphosphoryl azide
Synonyms
DPPA;DIPHENYL PHOSPHORAZIDATE;DIPHENYLPHOSPHONIC AZIDE;DIPHENYL AZIDOPHOSPHATE;diphenylphophoryl azide;Diphenylphosphorazindate(DPPA);Diphenyphosphoryl azide;Diphenyl azide phosphate;phosphorazidicacid,diphenylester;PS-DPPA
CBNumber:
CB3404964
Molecular Formula:
C12H10N3O3P
Molecular Weight:
275.2
MDL Number:
MFCD00001987
MOL File:
26386-88-9.mol
MSDS File:
SDS
Last updated:2024-03-27 17:16:15

Diphenylphosphoryl azide Properties

Boiling point 157 °C/0.17 mmHg (lit.)
Density 1.277 g/mL at 25 °C (lit.)
refractive index n20/D 1.551(lit.)
Flash point >230 °F
storage temp. 2-8°C
solubility Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly)
form Liquid
Specific Gravity 1.277
color slightly yellow
Water Solubility insoluble
Hydrolytic Sensitivity 7: reacts slowly with moisture/water
BRN 2058967
Stability Stable. Incompatible with acids, strong oxidizing agents.
InChIKey SORGEQQSQGNZFI-UHFFFAOYSA-N
CAS DataBase Reference 26386-88-9(CAS DataBase Reference)
FDA UNII GXM91165AV
NIST Chemistry Reference Diphenylphosphoryl azide(26386-88-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301+H311+H331-H315-H319-H335
Precautionary statements  P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
Hazard Codes  T
Risk Statements  23/24/25-36/37/38
Safety Statements  26-36/37/39-45
RIDADR  UN 3278 6.1/PG 2
WGK Germany  3
3-10
Hazard Note  Toxic/Keep Cold
TSCA  No
HazardClass  6.1
PackingGroup  III
HS Code  29299000
NFPA 704
1
3 1

Diphenylphosphoryl azide price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 178756 Diphenyl phosphoryl azide 97% 26386-88-9 5g $29.1 2024-03-01 Buy
Sigma-Aldrich 178756 Diphenyl phosphoryl azide 97% 26386-88-9 5kg $2480 2024-03-01 Buy
TCI Chemical D1672 Diphenylphosphoryl Azide >97.0%(GC) 26386-88-9 5g $25 2024-03-01 Buy
TCI Chemical D1672 Diphenylphosphoryl Azide >97.0%(GC) 26386-88-9 25g $67 2024-03-01 Buy
Alfa Aesar A12124 Diphenylphosphonic azide, 97% 26386-88-9 5g $24.65 2024-03-01 Buy
Product number Packaging Price Buy
178756 5g $29.1 Buy
178756 5kg $2480 Buy
D1672 5g $25 Buy
D1672 25g $67 Buy
A12124 5g $24.65 Buy

Diphenylphosphoryl azide Chemical Properties,Uses,Production

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.

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.
synthesis of Diphenyl Phosphorazidate (DPPA)
Diphenyl Phosphorazidate (DPPA) - More Than Three Decades Later
Takayuki Shioiri
Graduate School of Environmental and Human Sciences, Meijo University

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.

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.
Reactions of 26386-88-9

Mechanism of action

Diphenyl phosphoryl azide is used in the aziridination of olefins catalyzed by colbalt-tetraphenylporphyrin. It is also used as the activating agent in the preparation of macrocyclic lactams and of an aldose reductase inhibitor.

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View Lastest Price from Diphenylphosphoryl azide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Diphenylphosphoryl azide pictures 2024-03-28 Diphenylphosphoryl azide
26386-88-9
US $30.00 / kg 1kg 98% 2000kg hebei hongtan Biotechnology Co., Ltd
Diphenylphosphoryl azide pictures 2024-03-28 Diphenylphosphoryl azide
26386-88-9
US $2.00 / KG 1KG 99% 500mt/year Jinan Finer Chemical Co., Ltd
Diphenyl Azidophosphate (DPPA) pictures 2024-03-27 Diphenyl Azidophosphate (DPPA)
26386-88-9
US $0.00-0.00 / Kg 1Kg 99.9% 200tons airuikechemical co., ltd.
(PHO)2PO-N3 PHOSPHORIC ACID DIPHENYL ESTER AZIDE PS-DPPA Diphenylphosphonicazide,97% DPPA polymer-bound, PS-DPPA DPPA, Phosphoric acid diphenyl ester azide DIPHENYLPHOSPHORYL AZIDE DIPHENYLPHOSPHORYL AZIDE, POLYMER-BOUND DIPHENYLPHOSPHORIC AZIDE DPPA POLYMER-BOUND LABOTEST-BB LT00453991 AZIDOPHOSPHORIC ACID DIPHENYL ESTER Bis(phenoxy)phosphoryl-diazonioazanide Diphenylphosphoryl azide ,98% Diphenyl phosphoryl azide,DPPA, Phosphoric acid diphenyl ester azide Diphenyl phosphoryl DPPA, Diphenyl phosphorazidate, Diphenyl azidophosphonate Diphenylphosphoryl Azide (DPPA) Diphenyl phosphonyl azide Phosphorazidic acid, diphenyl ester Diphenylphoshoryl azide DIPHENYL AZIDOPHOSPHATE FOR SYNTHESIS Diphenyl phosphoryl azide 97% Azide diphenyl phosphate DPPA (Kg) {[Azido(phenoxy)phosphoryl]oxy}benzene Azidodiphenoxyoxophosphorane Diphenyl Azidophosphate (DPPA) DiphenylphosphorylAzide> Diphenylazidophosphat azido(benzyl)(oxo)(phenyl-l3-oxidaneylidene)-l6-phosphane Rufinamide Impurity 10 Diphenylphosphorazindate(DPPA) DIPHENYLPHOSPHONIC AZIDE DPPA Diphenyl azide phosphate phosphorazidicacid,diphenylester DIPHENYL PHOSPHORAZIDATE DIPHENYL AZIDOPHOSPHATE diphenylphophoryl azide Diphenyphosphoryl azide Relebactam Impurity 3 Diphenyl Phophoryl Azide(DPPA) 26386-88-9 26286-88-9 26386-88-6 C12H10N3O3P C12H10O3N3P C6H5O2PON3 Peptide Synthesis Amination Condensation & Active Esterification Coupling Reactions (Peptide Synthesis) C-X Bond Formation (Non-Halogen) Synthetic Reagents Azidation/Diazo Transfer Pharmaceutical Intermediates Peptide Coupling Reagents