Bromotripyrrolidinophosphonium hexafluorophosphate 三吡咯烷基溴化鏻六氟磷酸盐

规格: 97%
CAS: 132705-51-2
产品编号: H39515
MDL: MFCD00077412
品牌: INFI

缩合剂系列产品

一个氨基酸的氨基与另一个氨基酸的羧基可以缩合成肽，形成的酰胺键在蛋白质化学中称为肽键。目前多肽合成中，主要采用羧基活化方法来完成缩合反应，最早使用的是将羧基活化为酰卤、酰基叠氮、活性酯、对称酸酐以及混合酸酐的方法，但是由于这些条件存在氨基酸消旋、反应试剂危险以及制备比较复杂等问题，后来逐渐被缩合试剂取代。添加缩合剂则无需活化羧基，实验操作简单方便且绿色环保。在众多缩合剂中，磷正离子缩合剂使得非天然氨基酸及有空间位阻的氨基酸顺利的完成多肽合成，卤代试剂例如PyBroP、BOP-Cl适合位阻大的氨基酸合成，避免发生外消旋作用(图一)。缩合剂除了可以合成酰胺以外，还应用于酯的合成，反应条件更加温和并且减少副反应干扰。

图一：Journal of Medicinal Chemistry, 2012, 55(23), 10610-10629

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Chemical NameBromotripyrrolidinophosphonium hexafluorophosphate
CAS Number132705-51-2
Alfabeta NameBROMOTRIPYRROLIDINYLPHOSPHONIUMHEXAFLUOROPHOSPHATE V1(())--
MDL NumberMFCD00077412
Synonym BROMO-TRIS-PYRROLIDINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE PyBroP\(rg BROMO-TRIS-PYRROLIDINO-PHOSPHONIUM HEXFLUOROPHOSPHATE PyBroP PYBROP(TM) Bromo-tris-pyrrolidino-phosphonium hexafluorophosphat Bromotri(1-pyrrolidinyl)phosphonium hexafluorophosphate, 97% Pybrop(Bromo-Tris-PyrrolidinophosphoniumHexafluorophosphate) 溴-三吡咯烷基磷代六氟磷酸酯 PYBROP(R) Bromotri(pyrrolidin-1-yl)phosphoniumhexafluorophosphate PYBROP 三吡咯烷基溴化六氟磷酸盐 BROMOTRIPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE PyBroP® Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate ,97% Pyrrolidine phosphorus complex 三吡咯烷基溴化鏻六氟磷酸盐
PubChem Substance ID160871368
Beilstein Registry Number6842340
EC Number000-000-0
Chemical Name Translation三吡咯烷基溴化鏻六氟磷酸盐
Reaxys-RN6842340
GHS Symbol
Warnings IRRITANT
WGK Germany3
Precautionary statements
  • 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。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P302+P352+P332+P313+P362+P364
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P332+P313
  • P305+P351+P338+P337+P313
  • P302+P350
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P337+P313
    Hazard statements
    • H315 Causes skin irritation 会刺激皮肤
    • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
      Hazard Codes C Xi
      Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
      Signal word Danger Warning
      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；
      • S37 Wear suitable gloves 戴适当手套；
      • 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）；
      • S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服；
      • S36 Wear suitable protective clothing 穿戴适当的防护服；
        Risk Statements
        • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
        • R34 Causes burns 会导致灼伤
          Storage condition Moisture Sensitive -20°C <0°C 储存温度 -20°C
        • 多肽缩合剂，适宜于烃基双取代的氨基酸，用于Depsipeptide的合成。
        • {SA}
        • 1. Vassiliki Theodorou, et al Tetrahedron 67 , 5630-5634, (2011)
        • {SA}
        • 2. Fu-An Kang, et al Chem. Commun. 46 , 1347-1349, (2010)
        • {SA}
        • 3. Fu-An Kang, et al J. Am. Chem. Soc. 130 , 1130-11302, (2008)
        • {SA}
        • 4. Jordi Alsina, et al Lett. Pept. Sci. 6 , 243-245, (1999)
        • {SA}
        • 5. J. Coste et al. J. Org. Chem. 59 , 2437, (1994)
        • {SA}
        • 6. T. Kurome et al. Tetrahedron 52 , 4327, (1996)
        • {ALF} Efficient peptide coupling agent for N-methylated amino esters for which coupling with a number of conventional reagents has proved ineffective or slow, and giving superior results to 1H-Benzotriazol-1-yl&#x00AD;oxytri(1-pyrrolidinyl)&#x00AD;phosphonium hexafluorophosphate, B25251, in this type of reaction: J. Org. Chem., 59, 2437 (1994). See Appendix 6.
        • {ALF} Can also be used to activate formamides, e.g. reaction of DMF with primary amines to yield formamidines: Tetrahedron Lett., 40, 5487 (1999).
          • 132705-51-2 H39515 Bromotripyrrolidinophosphonium hexafluorophosphate 三吡咯烷基溴化鏻六氟磷酸盐

          化学属性

          Mol. FormulaC12H24BrF6N3P2
          Mol. Weight466
          TSCANo
          Density1.422
          Melting Point>100°C
          SolubilityDMF: 0.4 g/mL, clear
          Stability对湿度敏感

          *以上化合物性质及应用等信息仅供参考