Diphenylphosphoryl azide
- CAS No.
- 26386-88-9
- Chemical Name:
- Diphenylphosphoryl azide
- Synonyms
- DPPA;DIPHENYL PHOSPHORAZIDATE;DIPHENYL AZIDOPHOSPHATE;DIPHENYLPHOSPHONIC AZIDE;Diphenyl azide phosphate;PS-DPPA;diphenylphophoryl azide;Diphenylphosphorazindate（DPPA）;(PHO)2PO-N3;Diphenylazidophosphat
- CBNumber:
- CB3404964
- Molecular Formula:
- C12H10N3O3P
- Molecular Weight:
- 275.2
- MDL Number:
- MFCD00001987
- MOL File:
- 26386-88-9.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Product description | Number | Pack Size | Price |
| Diphenyl phosphoryl azide 97% | 178756 | 5g | $32 |
| Diphenyl phosphoryl azide 97% | 178756 | 5kg | $2730 |
| Diphenylphosphoryl Azide >97.0%(GC) | D1672 | 5g | $22 |
| Diphenylphosphoryl Azide >97.0%(GC) | D1672 | 25g | $55 |
| Diphenyl phosphoryl azide | 270706 | 5g | $293 |
| More product size | |||
| Boiling point | 157 °C/0.17 mmHg (lit.) |
|---|---|
| Density | 1.277 g/mL at 25 °C (lit.) |
| refractive index |
n |
| 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. |
| InChI | 1S/C12H10N3O3P/c13-14-15-19(16,17-11-7-3-1-4-8-11)18-12-9-5-2-6-10-12/h1-10H |
| InChIKey | SORGEQQSQGNZFI-UHFFFAOYSA-N |
| SMILES | [N-]=[N+]=NP(=O)(Oc1ccccc1)Oc2ccccc2 |
| CAS DataBase Reference | 26386-88-9(CAS DataBase Reference) |
| FDA UNII | GXM91165AV |
| NIST Chemistry Reference | Diphenylphosphoryl azide(26386-88-9) |
| UNSPSC Code | 12352302 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  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 | |||||||||
| target organs | Respiratory system | |||||||||
| PPE | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter | |||||||||
| 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 | |||||||||
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
|||||||||
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
|||||||||
| REACH Registrations | Active | |||||||||
| Limited Quantities | 100ml (liquid) or 0.5 Kg (solid) | |||||||||
| Excepted Quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) | |||||||||
| NFPA 704 |
|
Diphenylphosphoryl azide price More Price(87)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 178756 | Diphenyl phosphoryl azide 97% | 26386-88-9 | 5g | $32 | 2026-04-30 | Buy |
| Sigma-Aldrich | 178756 | Diphenyl phosphoryl azide 97% | 26386-88-9 | 5kg | $2730 | 2026-04-30 | Buy |
| TCI Chemical | D1672 | Diphenylphosphoryl Azide >97.0%(GC) | 26386-88-9 | 5g | $22 | 2026-04-30 | Buy |
| TCI Chemical | D1672 | Diphenylphosphoryl Azide >97.0%(GC) | 26386-88-9 | 25g | $55 | 2026-04-30 | Buy |
| Usbiological | 270706 | Diphenyl phosphoryl azide | 26386-88-9 | 5g | $293 | 2026-06-03 | 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.
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.
reaction suitability
reaction type: click chemistry
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
1of4
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Changzhou waston chemical technology Co.,Ltd | +86-051985861892 +8618112881323 | info@wastonchem.com | China | 314 | 58 |
| Nanjing Sinoda Biological Technology Co., Ltd | +8613401983379 | sales@njmcn.cn | CHINA | 74 | 58 |
| Shanghai Z&T Chemical Co., Ltd | +86-021-33561011 +8613818804961 | Sales@ztchemical.com.cn | China | 546 | 58 |
| Hebei Yanxi Chemical Co., Ltd. | +8618531123677 | faithe@yan-xi.com | China | 5853 | 58 |
| Hebei Chuanghai Biotechnology Co,.LTD | +86-86-13131129325 +8613131129325 | sales1@chuanghaibio.com | China | 5220 | 58 |
| Hebei Chuanghai Biotechnology Co., Ltd | +8615531151365 | mina@chuanghaibio.com | China | 18126 | 58 |
| Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 20120 | 58 |
| airuikechemical co., ltd. | +86-18353166132 | sales02@airuikechemical.com | China | 983 | 58 |
| Hebei Zhuanglai Chemical Trading Co.,Ltd | +8613343047651 | admin@zlchemi.com | China | 3692 | 58 |
| Capot Chemical Co.,Ltd. | +86-（0）57185586718 +86-13336195806 | sales@capot.com | China | 29640 | 60 |
Related articles
- A widely used coupling agent: Diphenylphosphoryl azide
- Diphenylphosphoryl azide is a well-known azide reagent used in peptide couplings, Curtius rearrangements, and Mitsunobu invers....
- Dec 1，2023
- The performance of diphenylphosphoryl azide
- Diphenylphosphoryl azide, originally developed by Yamada in 1972, has shown significant synthetic versatility, being used in i....
- Jan 28，2022
- What is Diphenylphosphoryl azide?
- Diphenylphosphonic azide acts as a reagent for the synthesis of peptides and phosphoramidates by reacting with amines. It is a....
- Apr 19，2021
Related Qustion
Ask a questionView Lastest Price from Diphenylphosphoryl azide manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-07-24 | Diphenylphosphoryl azide
26386-88-9
|
$2.00 | 1KG | 99% | 500mt/year | Jinan Finer Chemical Co., Ltd | |
 |
2026-07-09 | Diphenylphosphoryl azide
26386-88-9
|
$1.00-100.00 | 1KG | 99% | Henan Fengda Chemical Co., Ltd | ||
 |
2026-06-30 | Diphenylphosphoryl azide
26386-88-9
|
1kg | 98% | 1000kg | Shaanxi Dideu New Materials Co. Ltd |
-
- Diphenylphosphoryl azide
26386-88-9
- $2.00
- 99%
- Jinan Finer Chemical Co., Ltd
-
- Diphenylphosphoryl azide
26386-88-9
- $1.00-100.00
- 99%
- Henan Fengda Chemical Co., Ltd
-
- Diphenylphosphoryl azide
26386-88-9
- 98%
- Shaanxi Dideu New Materials Co. Ltd
26386-88-9(Diphenylphosphoryl azide)Related Search:
1of4
