Sodium hydride 氢化钠

规格: 60% dispersion in mineral oil
CAS: 7646-69-7
产品编号: H60072
MDL: MFCD00003471
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,OTsOMs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 hydride
Synonym sodium (I) hydride {uni_hamburg} SODIUM HYDRIDE, 55-65% (GASVOLUMETRIC) 氢化钠(60%分散在矿物油中) Sodiumhydride,60%inoil Sodium hydride inoil gray powder Sodium hydride dispersionin mineral oil 氢化钠, 57-63% OIL DISPERSION 氢化钠 氢化钠,油液分散氢化钠 SODIUM HYDRIDE, 60% DISPERSION IN MINERA L OIL sodiummonohydride 硫氫化鈉 NaH 氫化鈉 SODIUM HYDRIDE (60% DISPERSION) sodiumhydride[nah] SODIUM HYDRIDE Sodium hydride, 60% dispersion in mineral oil, in resealable cans Sodium monohydride NAH 80 Sodiumhydride,57-63%oildispersion Sodium hydride (NaH) SODIUM HYDRIDE, DRY, 95% NATRIUMHYDRID 60 %IGE SUSPENSION IN OEL nah80 Natriumhydrid sodium hydride sodiumhydride(nah) SodiumHydrideSuspension(60%InParaffinOil) Sodium hydride, 60%disp. in oil. In toluene or DMF solub. Bags SODIUM HYDRIDE DISPERSION
CAS Number7646-69-7
EC Number231-587-3
Beilstein Registry Number2384789
MDL NumberMFCD00003471
PubChem Substance ID24758
Merck Number8625
Chemical Name Translation钠氢60%
LabNetwork Molecule IDLN00195368
InChIInChI=1S/Na.H/q+1;-1
GHS Symbol
Signal word Danger
WGK Germany1
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • 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;
  • S33 Take precautionary measures against static discharges 对静电采取预防措施;
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
  • 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”
  • 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;
  • S7/8 Keep container tightly closed and dry 保存在严格密闭容器中,保持干燥;
    Risk Statements
    • R11 Highly flammable 非常易燃
    • R15 Contact with water liberates extremely flammable gases 遇水会释放出极端易燃的气体
    • R35 Causes severe burns 会导致严重灼伤
    • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
      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
      • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
      • 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。
      • P305+P351+P338
      • P305+P351+P338+P337+P313
      • P332+P313
      • 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
      • P370+P378
      • P402+P404
      • P422 Store contents under… 存储目录在…之下。
      • P501 Dispose of contents/container to..… 处理内容物/容器.....
        Hazard statements
        • H228 Flammable solid 易燃固体
        • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
        • 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。
        • H319 Causes serious eye irritation 严重刺激眼睛
          Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges dust mask type N95 (US), Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
          Packing GroupI
          UN Number 1427
          Storage condition Store at RT. Air & Moisture Sensitive 充氩保存 铝罐包装密封
          Hazard Codes 4.3 F F,C
          RTECSWB3910000
          Hazard Class4.3
          Warnings 危化品目录(2015)
        • 在有机合成中用作还原剂、缩合剂、烷基化试剂、氢化催化剂、克莱逊氏试剂,用作释氢剂。
        • {uni_hamburg} Short: II/24C
        • {ALF} CAUTION! Many literature procedures employ NaH in DMF, and this system is often used routinely by research workers as a 'convenient' general purpose strong base. It should be noted, especially when considering scale-up of such reactions, that thermal runaways have been observed with NaH/ DMF, with self-heating beginning at temperatures as low as 26oC in some cases: Chem. Eng. News, 60(28), 5; 60(37), 5 (1982). A similar effect was also noted with N,N-dimethylacetamide. More recently also, incidents have been reported with other dipolar aprotic solvents 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) and Dimethyl sulfoxide (DMSO): Org. Process. Res. Dev., 7, 1030 (2003).
        • {uni_hamburg} Short: II/24A
        • {ALF} For a review of sodium hydride-based complex reducing agents, see: Acta Chem. Scand., 44, 274 (1990).
        • {ALD} Merck: 14,8625
        • {ALF} Widely used strong base for the irreversible formation of Na derivatives. If required, the protective oil can be removed by repeated washing and decantation with low-boiling petroleum, see, e.g.: Org. Synth. Coll., 6, 684 (1988), but for many purposes, this is not necessary, and the oil can be removed by incorporating a suitable extraction or washing step in the work-up. There are numerous Organic Syntheses references to reactions using NaH.
        • {ALF} Used in the deprotonation of DMSO to form "dimsyl sodium", a useful strong base for e.g. the Wittig reaction: J. Org. Chem., 28, 1128 (1963).
        • 7646-69-7 H60072 Sodium hydride
氢化钠

          化学属性

          Mol. FormulaNaH
          Mol. Weight24
          Density1.2
          Melting Point800
          TSCAYes
          Solubility起反应
          Flash Point185°C
          Stability对湿度敏感
          Appearance powder (moistened with oil)