Tributyltin Hydride 三正丁基氢化锡

规格: 97%
CAS: 688-73-3
产品编号: H57821
MDL: MFCD00009416
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 NameTributyltin
Synonym Hydridotris(butyl)tin Stannane, tributyl- TBTHTri-n-butylstannane TIN TRIBUTYL HYDRIDE TRI-N-BUTYLTIN TRI-N-BUTYLTIN HYDRIDE TRIBUTYLSTANNANE TRIBUTYLTINHYDRIDE,TECHNICAL Tin, tri-n-butyl-, hydride Tri-n-butyl tin hydride Tri-n-butylstannane Tri-n-butyltin Tri-n-butyltin; Tributylstannane Tri-n-butyltinhydride,min.95% Tributylstannane Tributylstannyl hydride Tributylstannyl hydride solution Tributyltin Tributyltin hydride Tributylzinnhydrid tbth tri-n-butylstannanehydride tributyl-stannane 三丁基氢化锡 溶液 三正丁基氢化锡 三正丁基氢锡 氢化三丁锡
CAS Number688-73-3
EC Number211-704-4
Beilstein Registry Number3587329
MDL NumberMFCD00009416
PubChem Substance ID87577235
Reaxys-RN3587329
Chemical Name Translation三正丁基氢锡
Wiswesser Line Notation4-SN-H4&4
LabNetwork Molecule IDLN00193590
GHS Symbol
TYPE OF TEST            : LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1460 mg/m3/10M
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - lacrimation
   Behavioral - convulsions or effect on seizure threshold
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   NDRC** National Defense Research Committee, Office of Scientific Research
   and Development, Progress Report.  Volume(issue)/page/year:
   NDCrc-132,FEB1942

Signal word Danger
WGK Germany3
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • 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;
  • S35 This material and its container must be disposed of in a safe way 该物料及其容器必须以安全方式处置;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • 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);
  • 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;
  • 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;
  • S62 If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label where possible 吞食后不要催吐:立即求医并出示该容器或标签;
    Risk Statements
    • R10 Flammable 易燃
    • 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
    • R21 Harmful in contact with skin 与皮肤接触有害
    • R25 Toxic if swallowed 吞咽有毒
    • R30/38
    • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
    • R48/23/25
    • R50/53
    • R65 Harmful: may cause lung damage if swallowed 若吞咽可能伤害肺部器官
    • R67 Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
      Precautionary statements
      • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
      • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
      • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
      • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
      • 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。
      • 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。
      • P301+P310
      • P303+P361+P353
      • P305+P351+P338
      • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
      • P332+P313
      • P337+P313
      • P403+P235
      • P501 Dispose of contents/container to..… 处理内容物/容器.....
        Hazard statements
        • H315 Causes skin irritation 会刺激皮肤
        • H301 Toxic if swallowed 吞食有毒
        • H312 Harmful in contact with skin 皮肤接触有害
        • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
        • H319 Causes serious eye irritation 严重刺激眼睛
        • H372 Causes damage to organs through prolonged or repeated exposure 长期或频繁接触会损伤器官
        • H226 Flammable liquid and vapour 易燃液体和蒸气
        • H304 May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
        • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
        • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
        • H302+H332
        • H302 Harmful if swallowed 吞食有害
          Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
          RTECSWH8675000
          Packing GroupI
          UN Number 1993 2929 3399
          Storage condition Air & Moisture Sensitive 2-8℃保存。 0-10°C 0-10 储存温度2-8℃; 充氩保存 2-8°C
          Hazard Codes 3 4.3 T,N T,N,F
          Hazard Class6.1/3
          Warnings 危化品目录(2015)
        • 广泛使用的自由基试剂,可用于还原裂解、自由基脱卤以及分子内自由基环化。
        • {ALF} Dialdehydes and keto aldehydes undergo free-radical intramolecular pinacol coupling to give cyclic diols: J. Am. Chem. Soc., 117, 7283 (1995); J. Org. Chem., 63, 6357 (1998).
        • {ALD} Merck: 14,10451
        • Beilstein:4(4)4312
        • {
        • {uni_hamburg} Short: III/38A
        • {ALF} TBTH also cleaves other C-heteroatom bonds, controlled by the stability of the resulting radical: Nitro-groups at tertiary centers are readily cleaved: Synthesis, 693 (1986). Azides are readily reduced to amines: Synlett, 342 (1991). C-S and C-Se bonds are also cleaved. J. Am. Chem. Soc., 104, 2046 (1982); 112, 4008 (1990); J. Org. Chem., 49, 5206 (1984); 54, 1234 (1989).
        • {uni_hamburg} Short: III/35C4
        • {ALF} Reducing agent and source of tributyltin radicals. Widely used for selective reduction of alkyl halides to alkanes by a radical chain mechanism. The reaction is tolerant of a wide range of functionality, including OH and NH, in contrast to polar metal hydride reagents. For reviews, see: Synthesis, 499 (1970); 665 (1987). For a brief feature on uses of this reagent in synthesis, see: Synlett, 173 (2007). For use in the synthesis of deoxy sugars via reductive rearrangement of glycosyl bromides, see: Org. Synth. Coll., 8, 583 (1993). Cyclization of the initially-formed alkyl radical to a suitably positioned double bond may occur. Formation of 5-membered rings is strongly favoured, and ring closure onto an existing ring gives the cis-fused product. See, e.g.: J. Am. Chem. Soc., 108, 5893 (1986):
        • {ALF} Free-radical hydrostannylation of alkenes occurs with TBTH to give alkylstannanes. The reaction is catalyzed by, e.g. Rh complexes: Chem. Lett., 881 (1988), or Pd complexes: Angew. Chem. Int. Ed., 35, 1329 (1996), and refs therein. Syn-addition to alkynes gives vinylstannanes, useful intermediates which undergo electrophilic substitution reactions with retention of configuration. Thus, iodine, NIS and NBS give vinyl halides: J. Org. Chem., 47, 404 (1982); Tetrahedron, 42, 3575 (1986), and alkyllithium compoun
        • 688-73-3 H57821 Tributyltin Hydride 
三正丁基氢化锡

          化学属性

          Mol. FormulaC12H28Sn
          Mol. Weight291
          Density1.08
          Refractive index1.4710 to 1.4740
          Boiling Point80
          Flash Point40°C(lit.)
          TSCAYes
          Melting Point0-1°
          Solubility起反应
          Stability对空气, 湿度和热敏感