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Lithium bis(trimethylsilyl)amide 雙(三甲基硅基)氨基鋰

規(guī)格: 1.0 M solution in THF, SpcSeal
CAS: 4039-32-1
產(chǎn)品編號(hào): H12010
MDL: MFCD00008261
品牌: INFI

背景介紹

雙(三甲基硅基)氨基鋰(LiHMDS)又叫六甲基二硅基氨基鋰。可用于制備低配位數(shù)的金屬配合物，因?yàn)榕潴w的位阻很大。在有機(jī)合成或藥物合成中，雙(三甲基硅基)氨基鋰通常用作非親核性強(qiáng)堿，與其他大位阻有機(jī)強(qiáng)堿，如二異丙基氨基鋰，雙三甲基硅基氨基鉀，雙三甲基硅基氨基鈉等等相比，作用類(lèi)似，但堿性更強(qiáng)，在某些反應(yīng)中有其獨(dú)特的地方，有其他有機(jī)堿不具備的優(yōu)勢(shì)。

合成工藝

一種是在惰性氣體保護(hù)下，采用正丁基鋰或氫化鋰或氨基鋰奪取六甲基二硅胺烷的質(zhì)子，利用無(wú)水無(wú)氧的有機(jī)溶劑做反應(yīng)溶劑，低溫反應(yīng)。另一種方式是采用金屬鋰和六甲基二硅胺烷高溫反應(yīng)，同時(shí)使用三氯化鐵作為催化劑，反應(yīng)完全后，再用四氫呋喃溶劑溶解，制得六甲基二硅烷胺鋰四氫呋喃溶液。還有一種是惰性氣體保護(hù)下，向反應(yīng)容器中加入金屬鋰、異戊二烯、六甲基二硅氮烷和四氫呋喃，經(jīng)一步合成反應(yīng)得到最終產(chǎn)品。

應(yīng)用實(shí)例

1.文章報(bào)道利用LiHMDS和三氟甲磺酸酐一步法將酰胺脫氫轉(zhuǎn)化為烯酰胺，其中LiHMDS和磺酸酐添加順序至關(guān)重要，需要先添加LiHMDS，否則產(chǎn)率由92%下降至52%。反應(yīng)機(jī)理利用氘代實(shí)驗(yàn)證明，首先三氟甲磺酸酐將酰胺活化從而使N的α-氫酸化，之后發(fā)生去質(zhì)子化和消除得到烯酰胺產(chǎn)物[1]。

 

  

圖片來(lái)源于期刊：Journal of the American Chemical Society, 2021, 143, 10524-10529.


2.環(huán)狀聚合物具有獨(dú)特的物理化學(xué)和生物特性，但是合成具有很大的挑戰(zhàn)性。該文章研發(fā)出利用LiHMDS促進(jìn)環(huán)膨脹聚合的簡(jiǎn)單途徑，從N-烷基-N羧酸酐(NNCA)合成具有生物活性的大環(huán)[2]。

圖片來(lái)源于期刊：Journal of the American Chemical Society 2021, 143, 3697-3702.


參考文獻(xiàn)：

[1] Journal of the American Chemical Society, 2021, 143, 10524-10529.

[2] Journal of the American Chemical Society 2021, 143, 3697-3702.


Chemical NameLithium bis(trimethylsilyl)amide
CAS Number4039-32-1
EC Number223-725-6
Beilstein Registry Number3567910
MDL NumberMFCD00008261
Synonym (LiN(SiMe3)2) Li bis(TMS)A Lithium Bis(trimethylsilyl)amide (ca. 26% in Tetrahydrofuran, ca. 1.3mol/L) {} {} {} {} {} {} {} {} {} {} {} {} {} {PubChem} lithium bis(trimethylsilyl)amide {} {} {} {} {} {} {} {} {LY} Lithium bis(trimethylsilyl)amine,1.0M solution in THF,Safeseal {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Lithium bis(trimethylsilyl)amine,1.0M solution in THF,Safeseal {} {} {} {} {} {} {} {} {} {} {} {LY} Lithium bis(trimethylsilyl)amine,1.0M solution in THF,Safeseal {} {} {} {} {} {} {} {} {} {} {} {} {LY} Lithium bis(trimethylsilyl)amine,1.0M solution in THF,Safeseal {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Lithium bis(trimethylsilyl)amine,1.0M solution in THF,Safeseal {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Lithium bis(trimethylsilyl)amine,1.0M solution in THF,Safeseal {} {} {} {} {
PubChem Substance ID2733832
Reaxys-RN8136861
Chemical Name Translation雙(三甲基硅基)氨基鋰
InChIKeyYNESATAKKCNGOF-UHFFFAOYSA-N
LabNetwork Molecule IDLN00162852
InChIInChI=1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
Canonical SMILESC[Si]([N-][Si](C)(C)C)(C)C.[Li+]
GHS Symbol
Signal word Danger
WGK Germany3
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 遠(yuǎn)離火源，禁止吸煙；
  • S20 When using do not eat or drink 使用時(shí)，不得進(jìn)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；
  • S25 Avoid contact with eyes 避免眼睛接觸；
  • 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(yī)生意見(jiàn)；
  • S29 Do not empty into drains 不要排入下水道；
  • S30 Never add water to this product 切勿將水加入該產(chǎn)品中；
  • S33 Take precautionary measures against static discharges 對(duì)靜電采取預(yù)防措施；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴適當(dāng)?shù)姆雷o(hù)服、手套和眼睛/面保護(hù)；
  • 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(shí)使用（指明具體的消防器材種類(lèi)，如果用水增加危險(xiǎn)，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) 發(fā)生事故時(shí)或感覺(jué)不適時(shí)，立即求醫(yī)（可能時(shí)出示標(biāo)簽）；
  • S57 Use appropriate containment to avoid environmental contamination 使用適當(dāng)容器避免環(huán)境污染；
  • S60 This material and its container must be disposed of as hazardous waste 該物質(zhì)及其容器必須作為危險(xiǎn)廢物處置；
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免釋放到環(huán)境中，參考特別指示/安全收據(jù)說(shuō)明書(shū)；
  • 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：立即求醫(yī)并出示該容器或標(biāo)簽；
  • S7/8 Keep container tightly closed and dry 保存在嚴(yán)格密閉容器中，保持干燥；
  • S8 Keep container dry 保持容器干燥；
  • S9 Keep container in a well-ventilated place 保持容器在通風(fēng)良好的場(chǎng)所；
    Risk Statements
    • R11 Highly flammable 非常易燃
    • R14 Reacts violently with water 遇水會(huì)猛烈反應(yīng)
    • R19 May form explosive peroxides 可能生成易爆的過(guò)氧化物質(zhì)
    • R20 Harmful by inhalation 吸入有害
    • R34 Causes burns 會(huì)導(dǎo)致灼傷
    • R35 Causes severe burns 會(huì)導(dǎo)致嚴(yán)重灼傷
    • R37 Irritating to respiratory system 刺激呼吸道
    • R40 Limited evidence of a carcinogenic effect 有限證據(jù)表明其致癌作用
    • R48/20
    • R51/53
    • R62 Possible risk of impaired fertility 有削弱生殖能力的危險(xiǎn)
    • R63 Possible risk of harm to the unborn child 可能危害未出生嬰兒
    • R65 Harmful: may cause lung damage if swallowed 若吞咽可能傷害肺部器官
    • R67 Vapours may cause drowsiness and dizziness 蒸汽可能導(dǎo)致嗜睡和昏厥
      Precautionary statements
      • P201 Obtain special instructions before use. 使用前獲取專(zhuān)門(mén)指示。
      • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 遠(yuǎn)離熱源/火花/明火/熱的表面。——禁止吸煙。
      • P240 Ground/bond container and receiving equipment. 與地面接觸/連接集裝箱和接受設(shè)備。
      • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆電氣/通風(fēng)/照明/ .../設(shè)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。
      • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉塵/煙/氣體/煙霧/蒸汽/噴霧。
      • P264 Wash hands thoroughly after handling. 處理后要徹底洗凈雙手。
      • P264+P265
      • P270 Do not eat, drink or smoke when using this product. 使用本產(chǎn)品時(shí)不要吃東西，喝水或吸煙。
      • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通風(fēng)良好的地方使用。
      • P273 Avoid release to the environment. 避免釋放到環(huán)境中。
      • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防護(hù)手套/防護(hù)服/眼睛的保護(hù)物/面部保護(hù)物。
      • P301+P312
      • P301+P317
      • P301+P330+P331
      • P302+P352
      • P302+P361+P354
      • P303+P361+P353
      • P304+P312
      • P304+P340
      • P304+P340+P310
      • P305+P351
      • P305+P351+P338
      • P305+P354+P338
      • P308+P311
      • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或醫(yī)生/醫(yī)師。
      • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感覺(jué)不適，呼叫解毒中心或醫(yī)生/醫(yī)師。
      • P316
      • P317
      • P321 Specific treatment (see … on this label). 具體治療（見(jiàn)本標(biāo)簽上的）。
      • P322 Specific measures (see …on this label). 具體治療（見(jiàn)本標(biāo)簽上的）。
      • P330 Rinse mouth. 漱口
      • P362+P364
      • P363 Wash contaminated clothing before reuse. 被污染的衣服洗凈后方可重新使用。
      • P370+P378
      • P403+P233
      • P403+P235
      • P405 Store locked up. 上鎖保管。
      • P501 Dispose of contents/container to..… 處理內(nèi)容物/容器.....
        Hazard statements
        • H225 Highly flammable liquid and vapour 高度易燃液體和蒸氣
        • H228 Flammable solid 易燃固體
        • H302 Harmful if swallowed 吞食有害
        • H304 May be fatal if swallowed and enters airways 吞食和進(jìn)入呼吸道可能致命
        • H312 Harmful in contact with skin 皮膚接觸有害
        • H314 Causes severe skin burns and eye damage 導(dǎo)致嚴(yán)重的皮膚灼傷和眼睛損傷
        • H318 Causes serious eye damage 嚴(yán)重傷害眼睛
        • H332 Harmful if inhaled 吸入有害
        • H335 May cause respiratory irritation 可能導(dǎo)致呼吸道刺激
        • H336 May cause drowsiness or dizziness 肯能導(dǎo)致嗜睡或頭暈
        • H351 Suspected of causing cancer 懷疑致癌
        • H361 Suspected of damaging fertility or the unborn child 懷疑對(duì)生育能力或未出生嬰兒造成傷害
        • H361d Suspected of damaging the unborn child 懷疑對(duì)未出生嬰兒造成傷害
        • H373 May causes damage to organs through prolonged or repeated exposure 長(zhǎng)期或頻繁接觸可能會(huì)損傷器官
        • H411 Toxictoaquaticlifewithlonglastingeffects 對(duì)水生生物有毒性并具有長(zhǎng)期影響。
        • H412 Harmfutoaquaticlifewithlonglastingeffects 對(duì)水生生物有害并具有長(zhǎng)期影響。
          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) Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
          Packing GroupII
          UN Number 2924 UN2924
          Storage condition 2-8°C, sealed storage, away from moisture 87.0 below 5° C {} {} {} {} {} {} { {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {
          Hazard Codes 3 F,C
          Hazard Class3/8
          Restrict -
        • ⑴.也稱(chēng)二(三甲基硅基)氨基鋰。熔點(diǎn)71～72℃。沸點(diǎn)114～116℃(133.322Pa)。自燃，惰氣保護(hù)下密封貯運(yùn)。對(duì)空氣與水敏感。以硅氨在乙醚中與金屬鋰反應(yīng)而得。
        • ⑵.用于醛醇縮合，是常用的有機(jī)堿。例如形成乙炔化鋰，或者制備烯醇鋰鹽。
        • ⑶. 雙(三甲基硅基)氨基鋰可用于制備低配位數(shù)的配合物，因?yàn)榕潴w(TMS)2N-的位阻很大。這樣的例子有M[N(TMS)2]3（M = Sc, Ti, V, Fe ；TMS = (CH3)3Si)）。與三甲基氯硅烷反應(yīng)產(chǎn)生三(三甲基硅基)胺，其中氮的配位數(shù)為3，空間構(gòu)
        • 非親核性強(qiáng)堿，可用于形成烯醇的反應(yīng)，烯醇酯立體專(zhuān)一克萊森重排反應(yīng)，將醛轉(zhuǎn)化為硅亞胺的反應(yīng)，生成縮水甘油酸酯的反應(yīng)，β內(nèi)酰胺的反應(yīng)，芳基烷基醚的選擇性斷裂反應(yīng)。
        • {ALF} Supplied in septum cap bottle.
        • {ALF} Versatile non-nucleophilic strong base. For examples of use in the lithiation of ethyl acetate, see: Org. Synth. Coll., 6, 598 (1988), and in the stereospecific Wadsworth-Emmons synthesis of fluoroalkenes from (E)- and (Z)-fluorovinyl sulfones: Org. Synth. Coll., 9, 442 (1998).
          • 4039-32-1 H12010 Lithium bis(trimethylsilyl)amide 雙(三甲基硅基)氨基鋰
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          化學(xué)屬性

          Mol. FormulaC6H18LiNSi2
          Mol. Weight167.33
          Density0.87
          Boiling Point55 - 56 °C
          Flash Point-17 °C - (閉杯)
          TSCAYes
          Melting Point70 - 76 °C
          Solubility水解
          Refractive indexn20/D 1.425(lit.)
          Stability對(duì)空氣和濕度敏感
          Danger-Level甲類(lèi)
          pH-:-
          Redox-

          *以上化合物性質(zhì)及應(yīng)用等信息僅供參考