Diphenylphosphoryl azide
DPPA · DIPHENYL PHOSPHORAZIDATE · DIPHENYL AZIDOPHOSPHATE · DIPHENYLPHOSPHONIC AZIDE · Diphenyl azide phosphate · PS-DPPA · diphenylphophoryl azide · Diphenylphosphorazindate（DPPA）
Identifiers & Physical Properties
| CAS No. | 26386-88-9 |
|---|---|
| Molecular formula | C12H10N3O3P |
| Average molar mass | 275.2 g/mol |
| SMILES | [N-]=[N+]=NP(=O)(Oc1ccccc1)Oc1ccccc1 |
| InChIKey | SORGEQQSQGNZFI-UHFFFAOYSA-N |
| PubChem CID | 123414 |
| EC No. | 247-644-0 |
| DTXSID | DTXSID10949274 |
Chemical & Physical Properties
| XLogP | 4.4 |
|---|---|
| Topological polar surface area | 49.9 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 5 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 348 |
| Chemical classes | Other Uses -> Biochemical Research |
| Physical Description | Colorless odorless liquid[Alfa Aesar MSDS] |
| 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 conditions | 2-8°C |
| Solubility | Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly)insoluble |
| Physical state | Liquid |
| Specific gravity | 1.277 |
| Color | slightly yellow |
| 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 |
| GHS pictogram | GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301+H311+H331-H315-H319-H335 |
| GHS precautionary statements | P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | T |
| Risk statements (R) | 23/24/25-36/37/38 |
| Safety statements (S) | 26-36/37/39-45 |
| UN transport number | UN 3278 6.1/PG 2 |
| Water hazard class (WGK) | 3 |
| F | 3-10 |
| Hazard Note | Toxic/Keep Cold |
| TSCA inventory status | No |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Packing group | III |
| Customs code | 29299000 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 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) |
Safety & Regulations
| GHS classification | DangerH301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 81 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Status: Active Update: 11-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/20608Diphenyl azidophosphate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin and strong eye irritantToxic by ingestion, inhalation, and skin absorption[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 3 (97.5%) |
| Exposure control and personal protection | TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016]. |
| F | 3-10 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | No |
| UN transport number | UN 3278 6.1/PG 2 |
| Customs code | 29299000 |
| Risk statements (R) | 23/24/25-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS06 |
| Hazard symbols | T |
| hazard_note | Toxic/Keep Cold |
| Safety statements (S) | 26-36/37/39-45 |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | III |
| Target organs | Respiratory system |
| GHS hazard statements | H301+H311+H331-H315-H319-H335 |
| Limited quantities | 100ml (liquid) or 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338 |
Applications & Uses
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 & Synthesis
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