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Potassium bis(trimethylsilyl)amide 雙(三甲基硅基)氨基鉀

規格: 1.0 M solution in THF/Toluene（V/V=8/2）, SpcSeal
CAS: 40949-94-8
產品編號: H79914
MDL: MFCD00010330
品牌: INFI

產品介紹

雙(三甲基硅基)氨基鉀(KHMDS)與雙(三甲基硅基)氨基鋰(LiHMDS)和雙(三甲基硅基)氨基鈉(NaHMDS)是同系化合物，能夠溶于大多數有機溶劑，通常配置于乙醚、四氫呋喃和甲苯溶劑中使用。有非常強的堿性但親核性差，這是由于分子內具有兩個體積龐大且有親脂性的三甲基硅基(TMS)影響了它參與親核取代反應。常用于反應中的去質子化或作為堿性反應中的催化劑，應用于多種藥物分子合成。

合成工藝

經典合成方法用氫化鉀與六甲基硅氮烷在甲苯中回流反應。還有方法是利用金屬鉀與六甲基二硅氮烷在具有共軛不飽和鍵的電子載體苯乙烯存在下，在甲苯中回流反應得到雙(三甲基硅基)氨基鉀反應液。

應用(yong)實例

1. 氟(fu)型HFC-23是(shi)合成(cheng)(cheng)聚四氟(fu)乙(yi)烯的(de)工業副(fu)產品,是(shi)一種嚴重未充分利(li)用的(de)資(zi)源。文章(zhang)利(li)用HFC-23作(zuo)為廉價的(de)三氟(fu)甲(jia)基化試劑在具有(you)立體碳中(zhong)心(xin)的(de)手性(xing)胺上進行親核加成(cheng)(cheng)，合成(cheng)(cheng)富(fu)集對映體的(de)三氟(fu)甲(jia)基化乙(yi)二胺和含(han)有(you)兩個立體碳中(zhong)心(xin)的(de)異吲哚(duo)啉[1]。

圖片來源于期(qi)刊：The Journal of Organic Chemistry. 2020, 85, 7976-7985

2.文章描述利用雙(shuang)(三甲基硅基)氨(an)基鉀介導的(de)偶氮(dan)選擇性sp2 C-H硅基化反應，該方法條(tiao)件溫和簡單(dan)，即使對于一些復雜偶氮(dan)類藥物也(ye)能進行硅基化，并且具有一定的(de)選擇性[2]。

圖片(pian)來源(yuan)于期刊(kan)：Journal of the American Chemical Society. 2019, 141, 127-132

參考文(wen)獻：

[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 鉀鹽 溶液 雙(三甲基硅基)氨基鉀, 20% W/W, 0.91M IN THF 雙(三甲基硅烷基)氨基鉀 溶液 Potassium hexamethyldisilazide 六甲基二硅基胺基鉀 溶液 六甲基二硅基胺基鉀 溶液 六甲基二硅氮烷 鉀鹽 溶液
MDL NumberMFCD00010330
PubChem Substance ID3251421
Beilstein Registry Number4006754
EC Number424-100-2
CAS Number40949-94-8
Alfabeta NamePOTASSIUMBISTRIMETHYLSILYLAMIDE ()
Chemical Name Translation雙(三甲基硅烷基)氨基鉀
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.? 只能在室外或通風良好的地方使用。
  • P501 Dispose of contents/container to..… 處理內容物/容器.....
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 遠離熱源/火花/明火/熱的表面。——禁止吸煙。
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或醫生/醫師。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉塵/煙/氣體/煙霧/蒸汽/噴霧。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防護手套/防護服/眼睛的保護物/面部保護物。
  • P305+P351+P338
  • P403+P233
  • P305+P351+P338+P310
  • P264 Wash hands thoroughly after handling. 處理后要徹底洗凈雙手。
  • P301+P330+P331+P310
  • P201 Obtain special instructions before use. 使用前獲取專門指示。
  • P240 Ground/bond container and receiving equipment. 與地面接觸/連接集裝箱和接受設備。
  • P370+P378
  • P304+P340
  • P270 Do not eat, drink or smoke when using this product. 使用本產品時不要吃東西，喝水或吸煙。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆電氣/通風/照明/ .../設備。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉塵/煙/氣體/煙霧/蒸汽/噴霧。
  • P202 Do not handle until all safety precautions have been read and understood. 已閱讀并理解所有的安全預防措施之前，切勿操作。
  • P301+P310
  • P301+P310+P331
  • P273 Avoid release to the environment. 避免釋放到環境中。
  • P308+P311
    Hazard statements
    • H314 Causes severe skin burns and eye damage 導致嚴重的皮膚灼傷和眼睛損傷
    • H225 Highly flammable liquid and vapour 高度易燃液體和蒸氣
    • H302 Harmful if swallowed 吞食有害
    • H351 Suspected of causing cancer 懷疑致癌
    • H335 May cause respiratory irritation 可能導致呼吸道刺激
    • H304 May be fatal if swallowed and enters airways 吞食和進入呼吸道可能致命
    • H336 May cause drowsiness or dizziness 肯能導致嗜睡或頭暈
    • H361d Suspected of damaging the unborn child 懷疑對未出生嬰兒造成傷害
    • H373 May causes damage to organs through prolonged or repeated exposure 長期或頻繁接觸可能會損傷器官
      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 遇水會猛烈反應
      • R11 Highly flammable 非常易燃
      • R63 Possible risk of harm to the unborn child 可能危害未出生嬰兒
      • R48/20
      • R67 Vapours may cause drowsiness and dizziness 蒸汽可能導致嗜睡和昏厥
      • R65 Harmful: may cause lung damage if swallowed 若吞咽可能傷害肺部器官
      • R34 Causes burns 會導致灼傷
      • R19 May form explosive peroxides 可能生成易爆的過氧化物質
        Safety Statements
        • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 發生事故時或感覺不適時，立即求醫（可能時出示標簽）；
        • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接觸后，立即用大量水沖洗并征求醫生意見；
        • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴適當的防護服、手套和眼睛/面保護；
        • 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) 著火時使用（指明具體的消防器材種類，如果用水增加危險，注明“禁止用水”
        • S30 Never add water to this product 切勿將水加入該產品中；
        • S20 When using do not eat or drink 使用時，不得進食，飲水；
        • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入氣體/煙霧/蒸汽/噴霧；
        • S33 Take precautionary measures against static discharges 對靜電采取預防措施；
        • S16 Keep away from sources of ignition - No smoking 遠離火源，禁止吸煙；
        • S60 This material and its container must be disposed of as hazardous waste 該物質及其容器必須作為危險廢物處置；
        • S9 Keep container in a well-ventilated place 保持容器在通風良好的場所；
        • S8 Keep container dry 保持容器干燥；
          Storage condition Refrigerator Air & Moisture Sensitive 充氬保存
          Warnings IRRITANT
          Hazard Codes F,C
          Hazard Class3/8
          Restrict -
        • ⑴.常溫常壓條件下為液體。
        • ⑵.非親核性強堿。
        • ⑶.醫藥中間體，主要用于合成頭孢抗生素的生產。
        • 非親核性強堿。
        • {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 H79914 Potassium bis(trimethylsilyl)amide 雙(三甲基硅基)氨基鉀

          化學屬性

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

          *以(yi)上化合物性質及應(ying)用(yong)等信(xin)息僅供參考