Diphenyl Phosphoryl Azide (DPPA) 叠氮磷酸二苯酯

CAS 26386-88-9 MFCD00001987

化学结构图

26386-88-9
SMILES: [N-]=[N+]=NP(=O)(Oc1ccccc1)Oc1ccccc1

化学属性

Mol. FormulaC12H10N3O3P
Mol. Weight275
Refractive index1.5500 to 1.5540
Boiling Point157
Density1.273
Flash Point>110°(230°F)
TSCANo
Appearance 稳定液体。沸点157°C
Solubilityinsoluble
Stability对光敏感

别名和识别编码

Chemical NameDiphenyl 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 ID87568148
EC Number247-644-0
Beilstein Registry Number2058967
MDL NumberMFCD00001987
CAS Number26386-88-9
Reaxys-RN2058967
Chemical Name Translation叠氮磷酸二苯酯
LabNetwork Molecule IDLN00222521
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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
WGK Germany3
Hazard statements
  • 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
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Precautionary statements
  • 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.....
Signal word Danger
Packing GroupII
UN Number 3278
Risk Statements
  • 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
Safety Statements
  • 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);
Hazard Codes 6.1 T
Storage condition 密封避光保存 0-10 2-8°C 0-10°C
Hazard Class6.1

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)

系列性分类