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CAS RN: 26386-88-9 | 产品编码: D1672
Diphenylphosphoryl Azide
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技术规格
| Appearance | Colorless to Almost colorless clear liquid |
| Purity(GC) | min. 97.0 % |
物性（参考值）
| 比重 | 1.28 |
| 折射率 | 1.55 |
| 水溶性 | 与水接触发生分解, 不溶 |
GHS
| 象形图 |
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| 信号词 | Danger |
| 危险性说明 | H300 + H310 + H330 : Fatal if swallowed, in contact with skin or if inhaled. H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| 防范说明 | P501 : Dispose of contents/ container to an approved waste disposal plant. P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray. P270 : Do not eat, drink or smoke when using this product. P262 : Do not get in eyes, on skin, or on clothing. P271 : Use only outdoors or in a well-ventilated area. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P284 : Wear respiratory protection. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P361 + P364 : Take off immediately all contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth. P302 + P352 + P310 : IF ON SKIN: Wash with plenty of water. Immediately call a POISON CENTER/doctor. P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor. P403 + P233 : Store in a well-ventilated place. Keep container tightly closed. P405 : Store locked up. |
相关法规
运输信息
| UN编号 | UN3278 |
| 类别 | 6.1 |
| 包装类别 | II |
| HS编码* | 2929.90-000 |
应用
TCI Practical Example: Synthesis of a Carbamate Using DPPA
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Used Chemicals
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Procedure
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To a solution of thiazole-4-carboxylic acid (500 mg, 3.87 mmmol) and triethylamine (0.59 mL, 4.26 mmol, 1.1 equiv) in tert-butyl alcohol (2 mL) was added DPPA (0.92 mL, 4.26 mmol, 1.1 equiv) at 0 °C and stirred 30 min. Then, the reaction mixture was heated to 90 °C and stirred for 21 hours. After cooling to room temperature, the reaction mixture was removed under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate:hexane = 0:1 - 1:1 on silica gel) to give tert-butyl N-thiazol-4-ylcarbamate as a white solid (591 mg，y. 76%).
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Experimenter’s Comments
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The reaction mixture was monitored by LC.
TLC of the product: Rf = 0.4 (ethyl acetate:hexane = 1:4).
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Analytical Data
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tert-butyl N-thiazol-4-ylcarbamate
1H NMR (270 MHz, CDCl3); δ 8.58 (d, J = 2.2 Hz, 1H), 8.06 (brs, 1H), 7.29 (brs, 1H), 1.51 (s, 9H).
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Lead Reference
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- Novel Syntheses of Variably Substituted Pyrrolo[2,3-d]thiazoles
应用
Phosphoryl Azide for Nosylation via Azidation
Reference
- Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
应用
Phosphoryl Azide for Azidations
Reference
- Total Synthesis of Camptothecin and Related Natural Products by a Flexible Strategy
应用
Condensing Agent
Experimental procedure2): To an ice-cooled mixture containing 1 (2.5 mmol) and 2 (2.5 mmol) in dry DMF (15 mL), DPPA (3.0 mmol) is slowly added, followed by drop-wise addition of Et3N (6.3 mmol). The reaction mixture is kept at 0 °C for another 2 h, and then allowed to warm up to room temperature. After 24 h, the reaction mixture is diluted with EtOAc (80 mL) and washed with an aqueous solution of citric acid (10%, 50 mL), H2O (50 mL), saturated aqueous NaHCO3 (50 mL), H2O (50 mL), and brine (50 mL). The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue is purified by column chromatography to afford 3 (83% yield).
References
- 1)Diphenylphosphoryl azide. New convenient reagent for a modified Curtius reaction and for peptide synthesis
- 2)Novel Naphthalene-N-sulfonyl-D-glutamic Acid Derivatives as Inhibitors of MurD, a Key Peptidoglycan Biosynthesis Enzyme
应用
DPPA: A Stable and Easy-to-handle Azidating Agent
Experimental procedure2): Diphenylphosphoryl azide (0.87 mL, 4.04 mmol) is added to a solution of alcohol 1 (98 mg, 0.40 mmol), PPh3 (211 mg, 0.81 mmol) and DEAD (0.37 mL, 40% in toluene, 0.81 mmol) in THF (5 mL) and the reaction is stirred at room temperature for 24 h. Concentration in vacuo and purification by column chromatography (Et2O:hexanes = 1:9) gave 2 (108 mg, 0.40 mmol, 99%) as a colorless oil.
References
- 1)Phosphorus in organic synthesis-VII: Diphenyl phosphorazidate (DPPA). A new convenient reagent for a modified Curtius reaction
- 2)A Versatile Enantioselective Synthesis of Barrenazines
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