Sodium cyanoborohydride 氰基硼氢化钠

规格: 1.0 M solution in THF, SpcSeal
CAS: 25895-60-7
产品编号: H55156
MDL: MFCD00003516
品牌: INFI

简介

     氢化锂， 氢化铝锂，硼氢化钠，三乙基硼氢化锂(Super Hydride)/钠/钾 ，三仲丁基硼氢化锂( L-Selectride)/钠/钾(K-Selectride)， Lithium Trisiamylborohydride (LiBSia3H) 60217-34-7， 三叔丁氧基氢化铝锂，77299-63-9 Lithium diisobutyl-tert-butoxyaluminum hydride solution，Diisobutylaluminum hydride, DIBAL，硼烷四氢呋喃，氨基硼烷等,  金属氢化物，作为还原剂和负氢离子的来源，广泛用于无机和有机合成中，以及作为储氢材料应用到日常生产生活中。金属氢化物还原剂，可以还原取代卤代物到烷烃，醛酮环氧亚胺等到醇或胺，羧酸衍生物如酯，腈及其他衍生物到特别是某些烃基取代的金属化合物，具有反应条件温和，副反应少以及产率高的优点，体现出较好的化学选择性和立体 选择性。在复杂的天然产物，药物分子的合成中，较之其他还原法显示出更多的优点。

应用举例

1. 还原卤代物等到相应的烷烃（反应式A，B），并且氘代实验表明，该还原反应经过明确的SN2取代机理（反应式B）。另外，OTs，OMs等取代基也能被还原。


2. 还原环氧到醇，在如下例中，三乙基硼氢化锂比的四氢铝锂的选择性要高很多


3. 选择性还原醛酮到相应的醇。在alfa-环己酮的还原中，以很高的选择性的得到顺势的产品（反应式D）；并且，在醛和酮同时存在的情况下，可以优先还原醛到相应的一级醇（反应式E）。其中，Lithium trisiamylborohydride (LiBSia3H)表现出更好的选择性，以其他取代的环己酮为例，各氢化物还原总结如表一。


4. 选择性的还原羧酸及其衍生物。可以在有其他可被还原的基团存在下，选择性的还原酯基。

     5.其他用途。氢化物也可以转移负氢离子到其他的过度金属有机化合物上，形成新的M-H化合物，选择性的脱除甲基等等。



参考文献

  • Lithium Triethyllborohydride，Marek Zaidlewicz，Herbert C. Brown， Encyclopedia of Reagents for Organic Synthesis，2001
  • Krishnamutthy, S. Schubert R.M Brown, H, C, J., Am Chem. Soc 1973, 95, 8486
  • JACS, 1973


Chemical NameSodium cyanoborohydride
CAS Number25895-60-7
Synonym Sodium cyanotrihydridoborate Sodium borocyanohydride Sodium Cyanotrihydroborate(1-) Sodium cyanotrihydroborate 氰基硼氢化钠
MDL NumberMFCD00003516
Beilstein Registry Number4152656
PubChem Substance ID87575903
EC Number247-317-2
Merck Number8606
Reaxys-RN4152656
Chemical Name Translation氰基硼氢化钠
LabNetwork Molecule IDLN01305334
GHS Symbol
WGK Germany2
Precautionary statements
  • P223 Keep away from any possible contact with water, because of violent reaction and possible flash fire. 远离任何与水接触的可能，因为会剧烈反应可能产生闪火。
  • P231+P232
  • 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。
  • 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。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • 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+P330
  • P301+P330+P331+P310
  • P303+P361+P353
  • P303+P361+P353+P310+P363
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P335+P334
  • P370+P378
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P402+P404
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
    Hazard statements
    • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
    • H228 Flammable solid 易燃固体
    • H260 In contact with water releases flammable gases which may ignite spontaneously 与水接触时释放可燃气体，可自燃。
    • H300 Fatal if swallowed 吞食致命
    • H300+H310+H330
    • H301 Toxic if swallowed 吞食有毒
    • H301+H311+H331
    • H310 Fatal in contact with skin 皮肤接触致命
    • H311 Toxic in contact with skin 皮肤接触中毒
    • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
    • H330 Fatal if inhaled 吸入致命
    • H335 May cause respiratory irritation 可能导致呼吸道刺激
    • H351 Suspected of causing cancer 怀疑致癌
    • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
    • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
    • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
      Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
      Signal word
      Safety Statements
      • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中，参考特别指示/安全收据说明书；
      • 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；
      • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后，立即用大量…（由生产厂家指定）冲洗；
      • 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）；
      • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
      • S8 Keep container dry 保持容器干燥；
      • S1 Keep locked up 上锁；
      • S43 In case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add -?Never use water) 着火时使用（指明具体的消防器材种类，如果用水增加危险，注明“禁止用水”
      • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
      • S50 Do not mix with ... (to be specified by the manufacturer) 不要与……（由生产厂家指定）混合；
      • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
        Packing GroupII
        UN Number 3134
        Risk Statements
          Storage condition Moisture Sensitive Store under Argon 储存温度2-8°C,充氩储存 0-10°C 储存温度2-8°C ，充氩保护。 0-10
          Hazard Codes F,T+,N F,T,N T+,N
          Hazard Class4.3/6.1
        • 有机合成用还原剂，醛、酮、肟、烯胺类还原，β-内酰胺还原成β-氨基酸。氨的甲基化。
        • {ALF} Tosylhydrazones are reduced to methylenes. The relatively slow reduction of carbonyl compounds enables the tosylhydrazone to be generated in situ: J. Am. Chem. Soc., 93, 1793 (1971); 95, 3662 (1973). For a detailed study of the mechanism of tosylhydrazone reduction, see: J. Org. Chem., 54, 4175 (1989).
        • {ALF} Unlike borohydride reduction of carbonyl compounds which proceeds readily at the natural pH of the solution, reduction by sodium cyanoborohydride is very slow unless the pH is reduced to 3-4. Selective reduction of iminium ions occurs, however, at pH 6-8, leading to the widespread application of the reagent in reductive aminations of carbonyl compounds: J. Am. Chem. Soc., 93, 2897 (1971); Org. Synth. Coll., 6, 499 (1988). For improved methods using combinations with Ti(IV) chloride or isopropoxide, see: Tetrahedron Lett., 31, 5547 (1990); J. Org. Chem., 55, 2552 (1990).
        • {ALF} Oximes are reduced to hydroxylamines, as are O-alkyloximes: Tetrahedron Lett., 2493 (1974). Reduction in the presence of TiCl3 gives primary amines, via the imine: Synth. Commun., 18, 777 (1988).
        • {ALF} Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
        • {ALF} For reviews of the chemistry of sodium cyanoborohydride, see: Synthesis, 135 (1975); Org. Prep. Proced. Int., 11, 201 (1979).
          • 25895-60-7 H55156 Sodium cyanoborohydride 氰基硼氢化钠

          化学属性

          Mol. FormulaCH3BNNa
          Mol. Weight63
          Melting Point>242
          Density1.083 g/mL at 25 °C
          SolubilitySoluble in water, THF, methanol
          TSCAYes
          Flash Point-1 °F
          Appearance 白色或微黄色固体粉末，是一种温和的还原剂，它广泛用于醛、酮的还原，特别是酮的还原胺化作用。熔点242-243℃
          Boiling Point307°C
          Stability对湿度敏感