Diphenylphosphoryl azide

ChemicalBook > CAS DataBase List > Diphenylphosphoryl azide

Diphenylphosphoryl azide

Product Name: 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
Formula Weight: 275.2
MOL File: 26386-88-9.mol

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Diphenylphosphoryl azide Property

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)
NIST Chemistry Reference: Diphenylphosphoryl azide(26386-88-9)

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Safety

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
F: 3-10
Hazard Note: Toxic/Keep Cold
TSCA: No
HazardClass: 6.1
PackingGroup: III
HS Code: 29299000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 178756
Product name: Diphenyl phosphoryl azide
Purity: 97%
Packaging: 5g
Price: $29.1
Updated: 2024/03/01

Sigma-Aldrich

Product number: 178756
Product name: Diphenyl phosphoryl azide
Purity: 97%
Packaging: 5kg
Price: $2480
Updated: 2024/03/01

TCI Chemical

Product number: D1672
Product name: Diphenylphosphoryl Azide
Purity: >97.0%(GC)
Packaging: 5g
Price: $25
Updated: 2024/03/01

TCI Chemical

Product number: D1672
Product name: Diphenylphosphoryl Azide
Purity: >97.0%(GC)
Packaging: 25g
Price: $67
Updated: 2024/03/01

Alfa Aesar

Product number: A12124
Product name: Diphenylphosphonic azide, 97%
Packaging: 5g
Price: $24.65
Updated: 2024/03/01

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Diphenylphosphoryl azide Chemical Properties,Usage,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.

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 Later
Takayuki Shioiri
Graduate 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.

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.

Diphenylphosphoryl azide Preparation Products And Raw materials

Raw materials

Preparation Products

4H-AMINO-6-BROMO-2,3-DIHYDROTHIOCHROMEN-1,1-DIOXIDE 2-Thienyl isocyanate carfentrazone-ethyl Hexamethylene Diisocyanate 2-isocyanatopyridine 1-AMINO-CYCLOPROPANEMETHANOL 3-Cyanophenyl isocyanate 5-TERT-BUTOXYCARBONYLAMINO-PYRIDINE-3-CARBOXYLIC ACID 2-Chloro-6-fluoroaniline (2-FORMYL-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER 3-Amino-5-fluoropyridine (1R,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID 4,6-DICHLORO-PYRIDIN-3-YLAMINE 4-Aminobiphenyl 3-AMINO-6-PYRIDINEMETHANOL 5-ISOCYANATO-2-METHYL-PYRIDINE (2-BROMO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER (TRIMETHYLSILYL)DIAZOMETHANE

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View Lastest Price from Diphenylphosphoryl azide manufacturers

hebei hongtan Biotechnology Co., Ltd

Product: Diphenylphosphoryl azide 26386-88-9
Price: US $30.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 2000kg
Release date: 2024-03-22

airuikechemical co., ltd.

Product: Diphenyl Azidophosphate (DPPA) 26386-88-9
Price: US $0.00-0.00/Kg
Min. Order: 1Kg
Purity: 99.9%
Supply Ability: 200tons
Release date: 2024-04-08

Henan Fengda Chemical Co., Ltd

Product: Diphenylphosphoryl azide 26386-88-9
Price: US $100.00-1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2023-12-24

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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