diphenyl phosphorazidate
diphenyl azidophosphate
CAS: 26386-88-9
Molecular Formula: C12H10N3O3P
diphenyl phosphorazidate - Names and Identifiers
| Name | diphenyl azidophosphate |
| Synonyms | DPPA PS-DPPA (PHO)2PO-N3 DPPA POLYMER-BOUND diphenyl azidophosphate Diphenylphosphoryl azide diphenyl phosphorazidate DIPHENYLPHOSPHORIC AZIDE Diphenyl Phosphorylazide diphenylphosphinic azide DIPHENYLPHOSPHONIC AZIDE Diphenyl phosphoryl azide DPPA polymer-bound, PS-DPPA phosphorazidicacid,diphenylester PHOSPHORIC ACID DIPHENYL ESTER AZIDE DIPHENYLPHOSPHORYL AZIDE, POLYMER-BOUND DPPA, Phosphoric acid diphenyl ester azide |
| CAS | 26386-88-9 |
| EINECS | 247-644-0 |
| 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 |
| InChIKey | SORGEQQSQGNZFI-UHFFFAOYSA-N |
diphenyl phosphorazidate - Physico-chemical Properties
| Molecular Formula | C12H10N3O3P |
| Molar Mass | 275.2 |
| Density | 1.277 g/mL at 25 °C (lit.) |
| Boling Point | 157 °C/0.17 mmHg (lit.) |
| Flash Point | >230°F |
| Water Solubility | insoluble |
| Appearance | Liquid |
| Specific Gravity | 1.277 |
| Color | slightly yellow |
| BRN | 2058967 |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with acids, strong oxidizing agents. |
| Sensitive | 7: reacts slowly with moisture/water |
| Refractive Index | n20/D 1.551(lit.) |
| Physical and Chemical Properties | Appearance colorless to light yellow liquid |
diphenyl phosphorazidate - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 3278 6.1/PG 2 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 3-10 |
| TSCA | No |
| HS Code | 29299000 |
| Hazard Note | Toxic/Keep Cold |
| Hazard Class | 6.1 |
| Packing Group | III |
diphenyl phosphorazidate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | diphenyl azophosphate is a safe and efficient azide reagent obtained by reacting diphenyl chlorophosphate with sodium azide, which can replace sodium azide with explosion risk for azide reaction. DPPA can react with carboxylic acid to form an acyl azide intermediate, and then react with alcohol or amine to form N-substituted carbamates or amides. |
| Uses | Diphenyl azidophosphate is used for peptide coupling and 1,3-dipolar cycloaddition reactions; it is also used to prepare amino acid copolymers. It is widely used in organic synthesis, pharmaceutical synthesis and peptide compound synthesis. Azide reagent for aziridylation of olefins catalyzed by tetraphenylporphyrin-cobalt. It is also used as an activator for the preparation of macrocyclic lactam and aldose reductase inhibitors. It is also an important organophosphorus reagent. |
| preparation | 47.9g(0.178mol) of diphenyl chlorophosphate, 20.7g(0.32mol) of sodium azide and 2.5g of tetrabutylammonium bromide are added into a 100ml three-mouthed flask and stirred vigorously for 10 hours at room temperature. the mixture gradually becomes cloudy, sticky, and then becomes thinner, the color changes from colorless to light gray, and 42.5g of slightly light yellow or colorless viscous liquid can be obtained by filtering, the yield was 86.2% and the HPLC content was 99.3%. |
Last Update：2024-04-09 21:01:54
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