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Published TCIMAIL newest issue No.197
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CAS RN: 26386-88-9 | Product Number: D1672
Diphenylphosphoryl Azide
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Purity: >97.0%(GC)
Synonyms:
- DPPA
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 5G |
€17.00
|
28 | ≥40 |
|
| 25G |
€45.00
|
8 | ≥100 |
|
| 250G |
€278.00
|
5 | ≥40 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | D1672 |
| Purity / Analysis Method | >97.0%(GC) |
| Molecular Formula / Molecular Weight | C__1__2H__1__0N__3O__3P = 275.20 |
| Physical State (20 deg.C) | Liquid |
| Storage Temperature | Refrigerated (0-10°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive,Heat Sensitive |
| CAS RN | 26386-88-9 |
| Reaxys Registry Number | 2058967 |
| PubChem Substance ID | 87568148 |
| MDL Number | MFCD00001987 |
Specifications
| Appearance | Colorless to Almost colorless clear liquid |
| Purity(GC) | min. 97.0 % |
Properties (reference)
| Specific Gravity (20/20) | 1.28 |
| Refractive Index | 1.55 |
| Solubility in water | Decomposes in contact with water, Insoluble |
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H300 + H310 + H330 : Fatal if swallowed, in contact with skin or if inhaled. H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| Precautionary Statements | P262 : Do not get in eyes, on skin, or on clothing. P260 : Do not breathe mist or vapours. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. 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. |
Related Laws:
| EC Number | 247-644-0 |
Transport Information:
| UN Number | UN3278 |
| Class | 6.1 |
| Packing Group | II |
| HS Number | 2929900090 |
Application
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
Application
Phosphoryl Azide for Nosylation via Azidation
Reference
- Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
Application
Phosphoryl Azide for Azidations
Reference
- Total Synthesis of Camptothecin and Related Natural Products by a Flexible Strategy
Application
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
Application
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
PubMed Literature
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