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

規格: 1.0 M solution in THF, SpcSeal
CAS: 4039-32-1
產品編號: 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的金屬配合物，因為配體的位阻很大。在有機合成或藥物合成中，雙(三甲基硅基)氨基鋰通常用作非親核性強堿，與其他大位阻有機強堿，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，作用類似，但堿性更強，在某些反應中有其獨特的地方，有其他有機堿不具備的優勢。

合成(cheng)工藝(yi)

一(yi)(yi)種是在惰性氣體保護(hu)下，采用(yong)正丁基(ji)(ji)鋰(li)或(huo)氫(qing)化鋰(li)或(huo)氨基(ji)(ji)鋰(li)奪(duo)取六(liu)甲(jia)(jia)基(ji)(ji)二(er)硅胺烷(wan)的(de)質子，利用(yong)無水無氧的(de)有機溶劑(ji)做反(fan)應(ying)溶劑(ji)，低(di)溫反(fan)應(ying)。另一(yi)(yi)種方式是采用(yong)金屬(shu)鋰(li)和(he)六(liu)甲(jia)(jia)基(ji)(ji)二(er)硅胺烷(wan)高溫反(fan)應(ying)，同時使用(yong)三氯化鐵作(zuo)為(wei)催化劑(ji)，反(fan)應(ying)完全后，再用(yong)四氫(qing)呋(fu)喃溶劑(ji)溶解，制得(de)六(liu)甲(jia)(jia)基(ji)(ji)二(er)硅烷(wan)胺鋰(li)四氫(qing)呋(fu)喃溶液。還(huan)有一(yi)(yi)種是惰性氣體保護(hu)下，向(xiang)反(fan)應(ying)容器中加入金屬(shu)鋰(li)、異戊二(er)烯(xi)、六(liu)甲(jia)(jia)基(ji)(ji)二(er)硅氮烷(wan)和(he)四氫(qing)呋(fu)喃，經一(yi)(yi)步合成反(fan)應(ying)得(de)到(dao)最終產品。

應(ying)用實例(li)

1.文(wen)章報道利(li)用LiHMDS和(he)三(san)(san)氟甲磺酸(suan)酐一步法將(jiang)酰胺脫氫(qing)轉化(hua)為烯酰胺，其中LiHMDS和(he)磺酸(suan)酐添加順序至(zhi)關(guan)重要(yao)，需要(yao)先(xian)添加LiHMDS，否則(ze)產(chan)(chan)率由92%下(xia)降至(zhi)52%。反應(ying)機理利(li)用氘代實驗(yan)證明，首(shou)先(xian)三(san)(san)氟甲磺酸(suan)酐將(jiang)酰胺活(huo)化(hua)從而使N的α-氫(qing)酸(suan)化(hua)，之(zhi)后(hou)發生(sheng)去質子化(hua)和(he)消除得到(dao)烯酰胺產(chan)(chan)物[1]。

 

  

圖(tu)片來(lai)源于期(qi)刊：Journal of the American Chemical Society, 2021, 143, 10524-10529.


2.環(huan)狀聚合(he)物(wu)具有獨特的(de)(de)物(wu)理化(hua)學(xue)和(he)生物(wu)特性(xing)，但(dan)是合(he)成具有很(hen)大的(de)(de)挑戰(zhan)性(xing)。該(gai)文章研發出利(li)用LiHMDS促進環(huan)膨脹聚合(he)的(de)(de)簡單途徑，從N-烷基-N羧酸(suan)酐(NNCA)合(he)成具有生物(wu)活性(xing)的(de)(de)大環(huan)[2]。

圖片來源(yuan)于(yu)期刊(kan)：Journal of the American Chemical Society 2021, 143, 3697-3702.


參考文(wen)獻(xian)：

[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 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 {} {} {} {} {} {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,Safes
PubChem Substance ID2733832
Reaxys-RN8136861
Chemical Name Translation雙三甲基硅基胺基鋰
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 遠離火源，禁止吸煙；
  • 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；
  • 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生意見；
  • S29 Do not empty into drains 不要排入下水道；
  • S30 Never add water to this product 切勿將水加入該產品中；
  • S33 Take precautionary measures against static discharges 對靜電采取預防措施；
  • 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”
  • 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）；
  • S57 Use appropriate containment to avoid environmental contamination 使用適當容器避免環境污染；
  • 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；
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免釋放到環境中，參考特別指示/安全收據說明書；
  • 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：立即求醫并出示該容器或標簽；
  • S7/8 Keep container tightly closed and dry 保存在嚴格密閉容器中，保持干燥；
  • S8 Keep container dry 保持容器干燥；
  • S9 Keep container in a well-ventilated place 保持容器在通風良好的場所；
    Risk Statements
    • R11 Highly flammable 非常易燃
    • R14 Reacts violently with water 遇水會猛烈反應
    • R19 May form explosive peroxides 可能生成易爆的過氧化物質
    • R20 Harmful by inhalation 吸入有害
    • R34 Causes burns 會導致灼傷
    • R35 Causes severe burns 會導致嚴重灼傷
    • R37 Irritating to respiratory system 刺激呼吸道
    • R40 Limited evidence of a carcinogenic effect 有限證據表明其致癌作用
    • R48/20
    • R51/53
    • R62 Possible risk of impaired fertility 有削弱生殖能力的危險
    • 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 蒸汽可能導致嗜睡和昏厥
      Precautionary statements
      • P201 Obtain special instructions before use. 使用前獲取專門指示。
      • 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。
      • P240 Ground/bond container and receiving equipment. 與地面接觸/連接集裝箱和接受設備。
      • 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。
      • 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. 使用本產品時不要吃東西，喝水或吸煙。
      • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通風良好的地方使用。
      • P273 Avoid release to the environment. 避免釋放到環境中。
      • 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。
      • 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生/醫師。
      • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感覺不適，呼叫解毒中心或醫生/醫師。
      • P316
      • P317
      • P321 Specific treatment (see … on this label). 具體治療（見本標簽上的）。
      • P322 Specific measures (see …on this label). 具體治療（見本標簽上的）。
      • 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 導致嚴重的皮膚灼傷和眼睛損傷
        • H318 Causes serious eye damage 嚴重傷害眼睛
        • H332 Harmful if inhaled 吸入有害
        • H335 May cause respiratory irritation 可能導致呼吸道刺激
        • H336 May cause drowsiness or dizziness 肯能導致嗜睡或頭暈
        • H351 Suspected of causing cancer 懷疑致癌
        • H361 Suspected of damaging fertility or the unborn child 懷疑對生育能力或未出生嬰兒造成傷害
        • 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
        • H411 Toxictoaquaticlifewithlonglastingeffects 對水生生物有毒性并具有長期影響。
        • H412 Harmfutoaquaticlifewithlonglastingeffects 對水生生物有害并具有長期影響。
          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 {LY} 2-8°C, sealed storage, away from moisture 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 {} {} {} {} {} {} {} {} {} {} {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
          Hazard Codes 3 F,C
          Hazard Class3/8
          Restrict -
        • ⑴.也稱二(三甲基硅基)氨基鋰。熔點71～72℃。沸點114～116℃(133.322Pa)。自燃，惰氣保護下密封貯運。對空氣與水敏感。以硅氨在乙醚中與金屬鋰反應而得。
        • ⑵.用于醛醇縮合，是常用的有機堿。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的配合物，因為配體(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產生三(三甲基硅基)胺，其中氮的配位數為3，空間構
        • 非親核性強堿，可用于形成烯醇的反應，烯醇酯立體專一克萊森重排反應，將醛轉化為硅亞胺的反應，生成縮水甘油酸酯的反應，β內酰胺的反應，芳基烷基醚的選擇性斷裂反應。
        • {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

          化學屬性

          Boiling Point55-56 °C
          Flash Point-31°(-24°F)
          TSCAYes
          Melting Point-17
          Solubility水解
          Refractive indexn20/D 1.425(lit.)
          Stability對空氣和濕度敏感
          Density0.871
          Mol. FormulaC6H18LiNSi2
          Mol. Weight167.33
          Danger-Level甲類
          pH-:-
          Redox-

          *以上化合物(wu)性質及應(ying)用(yong)等信息僅供參考