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Sodium bis(trimethylsilyl)amide 雙(三甲基硅基)氨基鈉

規格: 2.0 M solution in THF, SpcSeal
CAS: 1070-89-9
產品編號: H12013
MDL: MFCD00009835
品牌: INFI

產品介紹

和去質子化得到其衍生物、還可以與鹵代烷烴反應得到胺的衍生物。

合成工藝

該產品與雙(三甲基硅基)氨基鋰生產工藝類似。有一種是由氫化鈉或氨基鈉與六甲基二硅氮烷在甲苯中回流反應。還有由金屬鈉和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1,4-二氧六環溶劑中回流反應，得到雙(三甲基硅基)氨基鈉。

應用實例(li)

1. 文章發展一(yi)種利(li)用堿(jian)金屬催化(hua)醛與(yu)甲(jia)(jia)苯(ben)的一(yi)鍋法氨(an)基(ji)芐(xia)基(ji)化(hua)反應(ying)。首先雙(三甲(jia)(jia)基(ji)硅基(ji))氨(an)基(ji)與(yu)碳(tan)酸(suan)銫原位(wei)生(sheng)產N-三甲(jia)(jia)基(ji)硅基(ji)醛亞(ya)胺，然(ran)后與(yu)甲(jia)(jia)苯(ben)衍生(sheng)物發生(sheng)芐(xia)基(ji)化(hua)反應(ying)，反應(ying)效率高且多種官能(neng)團耐受性好[1]。

圖片來源于期刊：Organic Letters. 2019, 21, 8514-8518

2. 文章中(zhong)的(de)(de)底(di)物利用雙(三甲基(ji)硅基(ji))氨基(ji)鈉烯(xi)醇(chun)化(hua)在不(bu)同溶劑溶劑和(he)底(di)物間表現出(chu)不(bu)同的(de)(de)選(xuan)擇(ze)性，只有在四氫呋(fu)喃中(zhong)表現出(chu)很好的(de)(de)立(li)體選(xuan)擇(ze)性，文獻(xian)中(zhong)利用密度(du)泛函理論計算對反應進(jin)行了詳細的(de)(de)研究(jiu)[2]。

圖(tu)片來源于期刊：Journal of the American Chemical Society. 2021, 143, 17452-17464

參考文(wen)獻：

[1] Organic Letters. 2019, 21, 8514-8518

[2]Journal of the American Chemical Society. 2021, 143, 17452-17464


Chemical NameSodium bis(trimethylsilyl)amide, 95+%, pure
Synonym HEXAM HMN NA SALT HMN-Na 溶液 六甲基二硅氮烷 鈉鹽 溶液 N-SODIUMHEXAMETHYLDISILAZANE N-Sodiohe N-Sodiohexamethyldisilazane N-Sodiumhexamethyldisilazane N-lithiohexamethyldisilazane NAHMDS Natrium-bis-(trimethylsilyl)-amid Natriumbis-(t SOD SODIU SODIUM BIS(TRIMETHYLSILYL)AMIDE SOL., ~0 .6 M IN TOLUENE SODIUM BIS(TRIMETHYLSILYL)AMIDE, ~1 M IN THF Sodium bis(trimethylsilyl)amide Sodium bis(trimethylsilyl)amide (95%) {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00009835
CAS Number1070-89-9
EC Number213-983-8
Beilstein Registry Number3629917
PubChem Substance ID2724254
Reaxys-RN3629917
Chemical Name Translation雙(三甲基硅基)氨基鈉
InChIKeyWRIKHQLVHPKCJU-UHFFFAOYSA-N
InChIInChI=1S/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
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；
  • 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；
  • 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）；
  • 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；
  • S8 Keep container dry 保持容器干燥；
    Risk Statements
    • R11 Highly flammable 非常易燃
    • R14 Reacts violently with water 遇水會猛烈反應
    • R14/15 Reacts violently with water, liberating extremely flammable gases 遇水劇烈反應，釋放出高度可燃氣體
    • R19 May form explosive peroxides 可能生成易爆的過氧化物質
    • R34 Causes burns 會導致灼傷
    • 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
    • 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
      • 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。
      • P233 Keep container tightly closed. ?保持容器密閉。
      • 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。
      • P241+P242+P243
      • 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
      • P301+P330+P331+P310
      • P302+P352
      • P302+P361+P354
      • P303+P361+P353
      • P303+P361+P353+P310+P363
      • P304+P312
      • P304+P340
      • P304+P340+P310
      • P305+P351+P338
      • P305+P351+P338+P310
      • 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。
      • P403+P233
      • 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
        • 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
        • 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
        • 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), type ABEK (EN14387) respirator filter
          Packing GroupII
          UN Number 2924 UN2924 UN3096
          Storage condition Moisture Sensitive 易吸潮，密封保存。充入惰性氣體，密閉保存。 Air & Moisture Sensitive 充氬保存 2-8°C
          Hazard Codes 3 F,C
          Hazard Class3/8
          Restrict -
        • ⑴. 常溫下為微黃色至淺灰色結晶粉末，一般溶于四氫呋喃溶液中。
        • ⑵. 與銠(I)催化共同作用可顯著加快苯乙炔的聚合反應。
        • ⑶.又稱雙(三甲基癸基)氨化鈉
        • Significantly accelerated the polymerization of pheneylacetylene in conjunction with rhodium (I) catalysis
        • {ALF} Sufficiently nucleophilic to act as a protected form of ammonia in the synthesis of primary amines from halides and tosylates: Chem. Ber., 117, 1250 (1984).
        • {ALF} Useful sterically hindered base (NaHMDS) for, e.g. generation of enolates, Wittig reagents or carbenes.
        • {ALF} In the Wittig reaction, gives Li salt-free product distribution patterns, with selective (Z)-alkene formation: Chem. Ber., 109, 1694 (1976); Tetrahedron Lett., 30, 2173 (1989). For formation of anions of benzylic phosphonates and subsequent ɑɑ-difluorination, see N-Fluorobenzenesulfonimide, L13955.
        • {ALF} Used as a base for the preparation of ester enolates: J. Am. Chem. Soc., 93, 4945 (1971). Has been found to be superior to LDA for preparation of (Z)-enolates of ketones under thermodynamic control: Tetrahedron Lett., 30, 2779 (1989).
        • {uni_hamburg} Short: EINECS
        • {ALD} Beilstein: 4,IV,4014
        • {uni_hamburg} Short: III/35F
        • {ALF} Found to give better yields than LiHMDS or KHMDS for the carbenoid reactions with Dibromomethane, A10456: Synthesis, 201 (1972); Angew. Chem. Int. Ed., 11, 326 (1972).
          • 1070-89-9 H12013 Sodium bis(trimethylsilyl)amide 雙(三甲基硅基)氨基鈉

          化學屬性

          Melting PointNo Data Available
          SolubilitySoluble in hexane, toluene, ether
          TSCAYes
          Flash Point-17°(1°F)
          Stability易吸潮
          Boiling Point
          Density0.9197
          Mol. FormulaC6H18NNaSi2
          Mol. Weight183.37
          Danger-Level-
          pH-:-
          Redox-

          *以上化合物性質及應用等(deng)信息(xi)僅供參考