Diphenyl Phosphoryl Azide (DPPA) 叠氮磷酸二苯酯
CAS 26386-88-9 MFCD00001987
化学结构图
SMILES: [N-]=[N+]=NP(=O)(Oc1ccccc1)Oc1ccccc1
化学属性
| Mol. Formula | C12H10N3O3P |
|---|---|
| Mol. Weight | 275 |
| Refractive index | 1.5500 to 1.5540 |
| Boiling Point | 157 |
| Density | 1.273 |
| Flash Point | >110°(230°F) |
| TSCA | No |
| Appearance | 稳定液体。沸点157°C |
| Solubility | insoluble |
| Stability | 对光敏感 |
别名和识别编码
| Chemical Name | Diphenyl Phosphoryl Azide (DPPA) |
|---|---|
| Synonym | (PHO)2PO-N3 AZIDOPHOSPHORIC ACID DIPHENYL ESTER DIPHENYL AZIDOPHOSPHATE DIPHENYL PHOSPHORAZIDATE DIPHENYLPHOSPHORIC AZIDE DIPHENYLPHOSPHORYL AZIDE DIPHENYLPHOSPHORYL AZIDE, POLYMER-BOUND DPPA DPPA 二苯基磷酰叠氮化物 DPPA polymer-bound, PS-DPPA DPPA POLYMER-BOUND DPPA, Phosphoric acid diphenyl ester azide Diphenyl phosphonyl azide Diphenylphosphonicazide,97% Diphenylphosphorazidate Diphenylphosphorazindate（DPPA） LABOTEST-BB LT00453991 PHOSPHORIC ACID DIPHENYL ESTER AZIDE PS-DPPA Phosphorazidic acid, diphenyl ester Phosphoric acid diphenyl ester azide 叠氮磷酸二苯酯 叠氮磷酸二苯酯（DPPA） |
| PubChem Substance ID | 87568148 |
| Beilstein Registry Number | 2058967 |
| MDL Number | MFCD00001987 |
| CAS Number | 26386-88-9 |
| Reaxys-RN | 2058967 |
| Chemical Name Translation | 叠氮磷酸二苯酯 |
| EC Number | 247-644-0 |
| LabNetwork Molecule ID | LN00222521 |
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分类
- {SA} Azidation/Diazo Transfer, C-X Bond Formation (Non-Halogen), Chemical Synthesis, Synthetic Reagents
- {SNA} Azidation/Diazo Transfer, Azide Sources, C-X Bond Formation (Non-Halogen), Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Synthetic Reagents
- {SNA} Azidation/Diazo Transfer, Azide Sources, C-X Bond Formation (Non-Halogen), Chemical Biology, Chemical Reagents, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Development Quantities for Research, Synthetic Reagents
- {SNA} Chemical Reagents, Azidation/Diazo Transfer, Azide Sources, C-X Bond Formation (Non-Halogen), Chemical Biology
产品应用
- 叠氮化试剂，用于四苯卟啉-钴催化的烯烃的氮丙啶化。 也用作制备大环内酰胺和醛糖还原酶抑制剂的激活剂。
相关文献及参考
- Pyrrolidine enamines of cyclic ketones undergo 1,3-dipolar cycloaddition followed by rearrangement with loss of N2 to the ring contracted N-phosphoryl amidine which can be base
- Li enolates unsubstituted at the ɑ-position can undergo diazo-transfer reactions to give the diazo carbonyl derivatives. With ɑ-alkyl amides, azide transfer occurs to give 3-amino-2H-azirines: Helv. Chim. Acta, 78, 1983 (1995). Enolates of ɑ-unsubstituted carboxamides, on treatment with the reagent, followed by di-t-butyl dicarbonate, give derivatives ɑ-amino acids: Helv. Chim. Acta, 79, 213 (1996):
- Under Mitsunobu conditions, converts alcohols directly to alkyl azides: Tetrahedron Lett., 1977 (1977). Alternatively, with 1,8-Diazabicyclo[5.4.0]undec-7-ene, A12449, activated (e.g. benzylic) chiral alcohols have been converted to the azides with inversion in high ee: J. Org. Chem., 58, 5886 (1993); for illustrative example, see: Org. Synth., 75, 31 (1997).
- In the presence of an amine, carboxylic acids are converted to acyl azides which undergo a modified Curtius reaction in the presence of an alcohol to give alkyl carbamates directly. With t-butanol, the resulting t-butyl carbamates can readily be converted to the free amines with mild acid. Malonic half-esters, e.g. Ethyl hydrogen malonate, A12627, give ɑ-amino acid derivatives: J. Am. Chem. Soc., 94, 6203 (1972); Chem. Pharm. Bull., 22, 1398 (1974); J. Org. Chem., 49, 185 (1984):
- N-protected amino acids are converted to acyl azides for use in a low racemization peptide coupling technique: J. Am. Chem. Soc., 94, 6203 (1972); Synthesis, 549 (1974); J. Org. Chem., 44, 3101 (197
- Enables decarbonylation reactions of aldehydes to be carried out at ambient temperature with a catalytic amount of Chlorotris(triphenylphosphine)rhodium(I), 10468, by regeneration of the catalyst from an inactive Rh carbonyl complex: J. Org. Chem., 57, 5075 (1992).
- Stable azide-transfer agent.
安全信息
GHS Symbol
- H300+H310+H330
- H315 Causes skin irritation 会刺激皮肤
- H331 Toxic if inhaled 吸入中毒
- H311 Toxic in contact with skin 皮肤接触中毒
- H301 Toxic if swallowed 吞食有毒
- H335 May cause respiratory irritation 可能导致呼吸道刺激
- H319 Causes serious eye irritation 严重刺激眼睛
- H301+H311+H331
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
- P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P284 Wear respiratory protection.? 佩戴呼吸保护装置。
- P301+P310
- P301+P310+P330
- P302+P350
- P302+P352+P310+P361+P364
- P304+P340+P310
- P305+P351+P338
- P305+P351+P338+P337+P313
- P332+P313
- P337+P313
- P403+P233
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
其他信息
- F:3-10
- 不溶于水,溶于大多数常规有机溶剂。遇光和接触湿气发生颜色变化和分解。化学性质活泼，作为叠氮化钠的替代物，广泛应用于有机合成当中。
- Alfa Aesar:叠氮磷酸二苯酯,97% Diphenylphosphonic azide, 97%(26386-88-9)
- Sigma Aldrich:26386-88-9(sigmaaldrich)
