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Potassium bis(trimethylsilyl)amide 双(三甲基硅基)氨基钾

规格: 0.5 M solution in toluene, SpcSeal
CAS: 40949-94-8
产品编号: H12639
MDL: MFCD00010330
品牌: INFI

产品介绍

双(三甲基硅基)氨基钾(KHMDS)与双(三甲基硅基)氨基锂(LiHMDS)和双(三甲基硅基)氨基钠(NaHMDS)是同系化合物，能够溶于大多数有机溶剂，通常配置于乙醚、四氢呋喃和甲苯溶剂中使用。有非常强的碱性但亲核性差，这是由于分子内具有两个体积庞大且有亲脂性的三甲基硅基(TMS)影响了它参与亲核取代反应。常用于反应中的去质子化或作为碱性反应中的催化剂，应用于多种药物分子合成。

合成工艺

经典合成方法用氢化钾与六甲基硅氮烷在甲苯中回流反应。还有方法是利用金属钾与六甲基二硅氮烷在具有共轭不饱和键的电子载体苯乙烯存在下，在甲苯中回流反应得到双(三甲基硅基)氨基钾反应液。

应用实例

1. 氟型HFC-23是合成聚四氟乙烯的工业副产品,是一种严重未充分利用的资源。文章利用HFC-23作为廉价的三氟甲基化试剂在具有立体碳中心的手性胺上进行亲核加成，合成富集对映体的三氟甲基化乙二胺和含有两个立体碳中心的异吲哚啉[1]。

图片来源于期刊：The Journal of Organic Chemistry. 2020, 85, 7976-7985

2.文章描述利用双(三甲基硅基)氨基钾介导的偶氮选择性sp2 C-H硅基化反应，该方法条件温和简单，即使对于一些复杂偶氮类药物也能进行硅基化，并且具有一定的选择性[2]。

图片来源于期刊：Journal of the American Chemical Society. 2019, 141, 127-132

参考文献：

[1]The Journal of Organic Chemistry. 2020, 85, 7976-7985

[2]Journal of the American Chemical Society. 2019, 141, 127-132

Chemical NamePotassium Bis(Trimethylsilyl)Amide
Synonym 六甲基二硅氮烷 钾盐 溶液 双(三甲基硅基)氨基钾, 20% W/W, 0.91M IN THF 双(三甲基硅烷基)氨基钾 溶液 Potassium hexamethyldisilazide 六甲基二硅基胺基钾 溶液 六甲基二硅基胺基钾 溶液 六甲基二硅氮烷 钾盐 溶液
MDL NumberMFCD00010330
PubChem Substance ID3251421
Beilstein Registry Number4006754
EC Number424-100-2
CAS Number40949-94-8
Alfabeta NamePOTASSIUMBISTRIMETHYLSILYLAMIDE ()
Chemical Name Translation双(三甲基硅烷基)氨基钾
Reaxys-RN4006754
LabNetwork Molecule IDLN00163929
InChIInChI=1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
InChIKeyIUBQJLUDMLPAGT-UHFFFAOYSA-N
GHS Symbol
WGK Germany3
Precautionary statements
  • 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。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • 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。
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • 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
  • P403+P233
  • P305+P351+P338+P310
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P301+P330+P331+P310
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P370+P378
  • P304+P340
  • 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。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • 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。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P301+P310
  • P301+P310+P331
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P308+P311
    Hazard statements
    • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
    • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
    • H302 Harmful if swallowed 吞食有害
    • H351 Suspected of causing cancer 怀疑致癌
    • H335 May cause respiratory irritation 可能导致呼吸道刺激
    • 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
    • H361d Suspected of damaging the unborn child 怀疑对未出生婴儿造成伤害
    • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
      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 Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
      Signal word
      Packing GroupII
      UN Number UN2924
      Risk Statements
      • R14 Reacts violently with water 遇水会猛烈反应
      • R11 Highly flammable 非常易燃
      • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
      • R48/20
      • R67 Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
      • R65 Harmful: may cause lung damage if swallowed 若吞咽可能伤害肺部器官
      • R34 Causes burns 会导致灼伤
      • R19 May form explosive peroxides 可能生成易爆的过氧化物质
        Safety Statements
        • 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）；
        • 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；
        • 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”
        • S30 Never add water to this product 切勿将水加入该产品中；
        • S20 When using do not eat or drink 使用时，不得进食，饮水；
        • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾；
        • S33 Take precautionary measures against static discharges 对静电采取预防措施；
        • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
        • 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；
        • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
        • S8 Keep container dry 保持容器干燥；
          Storage condition Refrigerator Air & Moisture Sensitive 充氩保存
          Warnings IRRITANT
          Hazard Codes F,C
          Hazard Class3/8
          Restrict -
        • ⑴.常温常压条件下为液体。
        • ⑵.非亲核性强碱。
        • ⑶.医药中间体，主要用于合成头孢抗生素的生产。
        • 非亲核性强碱。
        • {ALF} Also used in the Wittig reaction, to give Li salt-free product distribution for selective (Z)-alkene formation: J. Org. Chem., 45, 4260 (1980). Has also been used with 18-crown-6 for selective formation of (Z)-ɑß-unsaturated esters from phosphonates: Tetrahedron Lett., 24, 4405 (1983).
        • {ALF} Sterically hindered strong base, compare Sodium bis(trimethyl­silyl)­amide, L13352 and Lithium bis(trimethyl­silyl)­amide, L15012. Used in the generation of K enolates, preferred to their Li or Na counterparts in some reactions, see e.g.: Tetrahedron Lett., 32, 1779 (1991); J. Am. Chem. Soc., 109, 6881 (1987); 111, 1063 (1989).
          • 40949-94-8 H12639 Potassium bis(trimethylsilyl)amide 双(三甲基硅基)氨基钾

          化学属性

          Refractive index1.4920
          Flash Point-14°(6°F)
          TSCANo
          Boiling Point66°
          Vapor Density3.2 (vs air)
          Vapor Pressure54 mmHg ( 25 °C)
          Stability对湿度敏感
          Density0.912
          Mol. FormulaC6H18KNSi2
          Mol. Weight199.48
          Danger-Level甲类
          pH-:A
          Redox-

          *以上化合物性质及应用等信息仅供参考

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