有机硅烷综述 硅烷保护及其衍生试剂 有机硅烷用作还原剂 交叉偶联化学中的硅烷 烯丙基甲硅烷用于稳定 α- 碳负离子和 β- 碳正离子

Transcription

1 有机硅烷综述 硅烷保护及其衍生试剂 有机硅烷用作还原剂 交叉偶联化学中的硅烷 烯丙基甲硅烷用于稳定 α- 碳负离子和 β- 碳正离子

2 引言 在有机化学中, 有机硅烷的运用形式很多, 其常用于保护有机合成中间产物的官能团 Acros rganics 有机硅烷系列将不断 扩大以满足您的化学需求 通过本文, 您可以了解有机硅烷 4 种最重要的应用 : 1,2 硅烷保护及其衍生试剂 3 有机硅烷用作还原试剂 4 交叉偶联化学中的硅烷 4 烯丙基硅烷用于稳定 α- 碳氟离子和 β- 碳正离子 有机硅保护及其衍生试剂 硅保护基是最常用的保护基团, 没有它, 现代天然产物合成将变得极为不便 5 硅烷化试剂通常用于保护醇类和酚类, 也 用于保护氨基 羧基 酰胺 硫醇以及炔烃 硅上可以连接不同的取代基, 被保护官能团的空间构象和电子特征也随之改变, 使得反应和脱保护反应的条件多样化 离 去的官能团和硅保护基团的选择在反应中起很重要的作用, 三甲基氯硅烷 [ 产品代号 :42643] 在反应中生成氯化氢, 其它的 TMS 保护试剂在反应中生成中性或者碱性的副产物 例如,N,N- 二乙基三甲基硅烷基胺 [15569] 是很强的硅烷化式, 反应中生成易挥 发的二乙胺, 然而烯丙基三甲基硅烷 [19699] 用于保护羧基和硫醇, 其在反应的过程中生成副产物丙烯 6 由于硅对氟有较高的亲和性, 使用四丁基氟化铵 [20195] 可以脱去硅保护基 四丁基氟化铵能和许多保护基团和官能团共存 硅保护基团的稳定性取决于介质的 ph 反应条件 立体和电子效应, 通常来说, 其稳定性与水解条件有关 7 Acidic hydrolysis: 3 < Ph 2 < Et 3 < t Bu 2 < i Pr 3 < t BuPh 2 Basic hydrolysis: 3 ~ Ph 2 < Et 3 < t Bu 2 ~ t BuPh 2 < i Pr 3 Acros rganics 近来引进了采用 AcroSeal 包装的一系列常用的氯硅烷,AcroSeal 包装方便使用, 并且能够很好地保护试剂免受湿气的影响 Acros rganics 已经有很多的甲基硅烷保护合成中间体, 这里列举出几个典型的产品 对于更多的产品, 可以在文章后面的产品清单上看到或者登陆 浏览 H N H Br H B N H [33784] [43024] [42817] [42817] [43869] 参考文献 1. Greene, T.; Wuts, P.; Protecting Groups in rganic Synthesis, 2nd Ed., Wiley, New York, Blau, K.; Halket, J.; Handbook of Derivatives for Chromatography, 2nd Ed., J. Wiley and Sons, New York, Chatgilialoglu, C.; Acc. Chem. Res., 1992, 25, Coats, R. M.; Denmark, S.; Handbook of Reagents for rganic Synthesis. Reagents, Auxillaries and Catalysts for C-C Bond Formation ; J. Wiley and Sons, GB, Kocienski; P. J.; Protecting Groups, 3rd Ed., Thieme: Stuttgart, Morita, T. et al.; Tetrahedron Lett., 1983, 21, Nelson, T. D.; Crouch, R. D.; Synthesis, 1996,

3 以下试剂是采用 AcroSeal 包装试剂的有机氯硅烷保护基团试剂 Group Reagent Code Notes 3 (TMS) Chlorotrimethylsilane Chlorotrimethylsilane, 1M solution in THF Chlorotrimethylsilane, 1M solution in DCM Et 3 (TES) Chlorotriethylsilane, 1M solution in THF t Bu 2 (TBDMS) t BuPh 2 (TBDPS) Used for the protection of alcohols, alkynes, amines and amino acids, carboxylic acids, phenols, ketones. Most easily cleaved of all silyl protecting groups in acid and base. Used for the protection of alcohols. TES ethers can be selectively deprotected in the presence of TBDMS ethers 8. tert-butyldimethylsilyl chloride, 1.0M in DCM tert-butyldimethylsilyl chloride, 50 wt.% in Ph Used for the protection of alcohols, amines, thiols, lactams and carboxylic acids. Reaction with an alcohol requires a catalyst such as imidazole. BDCS, silylation reagent [20094] is a convenient, ready-to-use DMF solution of TBDMSCl (0.5M) and imidazole (1.0M). tert-butylchlorodiphenylsilane Greater steric demand. Therefore, more stable than TBDMS to acid hydrolysis (>100x). Primary alcohols are protected in the presence of secondary alcohols. Ph 2 Dichlorophenylsilane Used for the protection of diols, diamines and hydroxyacids. 9 和硅烷化试剂反应产生的衍生物可以采用气相色谱 (GC) 分析 对于分子中含有羧酸 羟基 氨基 硫醇 磷酸盐等官能团的物质, 气相色谱法无法分析其成分, 可以将其转换成极性小 易挥发 热稳定性好的硅烷化的衍生品, 这样就能够采用气相色谱分析 以下是 Acros rganics 产品中典型的衍生试剂 Derivatisation Reagent Code Structure Notes N,-Bis(trimethylsilyl)acetamide N Commonly used derivatisation agents for acidic functional groups; i.e., alcohols, enols, amines, amides, carboxylic acids, amino acids, 2, 10 phenols, steroids, biogenic amines, alkaloids, phosphites and thiols. N,-Bis(trimethylsilyl)trifluoroacetamide N,-Bis(trimethylsilyl)trifluoroacetamide, with 1% TMSCl N,-Bis(trimethylsilyl)trifluoroacetamide, packaged in 1 ml ampoules F F F N ne of the most potent silylation reagents used today. It has two advantages over BSA in GC analysis: i) The by-products and the reagent itself are highly volatile so they cause minimal interference with the GC analysis. ii) The presence of fluorine atoms results in less fouling of flameionisation detectors. [38932] contains 1% TMSCl, which increases the silylating power of the mixture for analytical derivatisations. N-thyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) F N F F MSTFA and its by-product are even more volatile than BSTFA and its by-product. Used in the analysis of steroids 11, fatty acids 12 and nucleic acids by GC/MS. Dichloromethylsilane AcroSeal Cl Cl Used for derivatisation of diols, diamines and hydroyxacids. 参考文献 8. Toshima et al.; Tetrahedron Lett. 1989, 30, Barlos, K. et al.; J. rg. Chem., 1982, 47, Knapp, D. R.; Handbook of Analytical Derivatization Reactions John Wiley & Sons, New York, Donike, M.; Zimmermann, J.; J. Chromatogr., 1980, 202, Blum, W.; J. High Res. Chromatogr., Chromatogr. Commun., 1985, 718 & 1986,

4 有机硅烷用作还原剂 有机硅烷中的硅上连接多个 H 原子, 使得其具有类似离子或自由基性质的还原能力 改变连接到硅上的官能团能够改变 -H 键的特性, 从而使有机硅烷试剂用于特定的还原反应 当反应底物为醇类 烯烃 酯类 内酯 醛类 酮类 缩醛类 缩酮类 亚胺等碳正离子中间体时, 可以被三乙基硅烷 [21292] 还原, 三乙基硅烷通常在酸性条件下使用 三苯基硅烷 [16482] 和三甲基硅 烷 [29106] 可代替三正丁基氢化锡用于自由基还原 13 有机硅烷还原反应的范围列举在下面 相对于传统的还原试剂如氢化铝锂 三正丁基氢化锡, 这些有机硅烷和还原反应副产物比较安全而且容易处理 Acros rganics 能够提供各种参与官能团还原反应的硅氧化物 lyl hydride Acros rganics Code Cl 3 H Et 3 H Ph 3 H Ph 2 H PhH TMS 3 H PMHS (a) ( (a) 高分子质量还原试剂 氢化硅烷化 炔烃 烯烃以及酮类和硅氢化物可进行自由基氢化硅烷化反应 其区域和立体选择性与底物的取代基 有机硅烷以及所用的催化剂有关 例如, 使用 [CpRu(CN)3]PF[37789] 14 时, 三乙氧基硅烷和一系列端炔 [16481] 反应, 生成 α- 乙烯基硅烷, 并且产率较高 TBDPS (Et) 3 H [16481] TBDPS TBDPS (Et) 3 [CpRu(CN) 3 ]PF 6 [37789] 0 C to r.t, 1 h, DCM (Et) 3 20 : 1 (87% yield) α β 参考文献 13. Burke, S. D.; Danheiser. R.; Handbook of Reagents for rganic Synthesis - xidising and Reducing Reagents John Wiley and Sons Ltd., Trost, Barry M.; Ball, Zachary T. ; J. Am. Chem. Soc., 2005, 127,

5 交叉偶联化学中的硅烷 通过使用有机金属化合物, 许多金属催化偶联方法可以用于合成 C-C 键 例如 Stille (Sn),Kumada (Mg),Suzuki (B) 以及 Negishi (Zn) 偶联 有关这类方法的概述, 可以登入 Acros rganics 的官网 查看钯催化偶联反应手册 Hiyama 偶联是典型的钯或镍催化的机卤化物或三氟甲烷磺酸与有机硅烷的偶联反应 15 有机硅烷代替有机金属试剂(Mg Zn 和 Sn) 更有优势, 因为他们毒性低 化学稳定性好以及容易处理 用氟化物激活有机硅烷, 可以提高偶联反应速率 氟化物可以使硅化物 RR' 3 转化为更易金属化的 R-R' 3 F 中间体, 也可以 选择强碱以提高反应速率许多有机硅化合物可以发生偶联反应, 如二烷基硅醇基 16 三烷氧基硅烷 R R H dialkylsilanols R R R trialkoxysilanes R2-X Pd(0) catalyst Fluoride source or base R2- where R= normally or Et = Aryl, alkenyl, alkynyl, allyl, (alkyl) R2 = aryl, alkenyl, allyl 三烷氧基硅烷 17,18 正硅酸甲酯 [20382] 和正硅酸乙酯 [42036] 与有机金属试剂反应能够制备合成三甲氧基和三乙氧基硅烷, 或者在过渡金属 催化作用下, 三乙氧基硅烷 [16481] 进行硅烷化 有机三甲氧基硅烷与芳基氯 溴化物 乙烯卤化物 芳基三氟甲磺酸 烯丙基 20,21,22 苯甲酸发生 Hiyama 反应, 三甲氧基硅烷作为偶联剂 X X= Br, I i) Mg ii) (R) 4 or i) Rh or Pd catalyst ii) (R) 3 H (R) 3 Bz + + X R2 X= Cl, Br Et Et Et 3 mol % Pd(Ac) 2 3 mol % IPrHCl 2 eq. TBAF in THF/dioxane or {[(t-bu) 2 P(H)(t-Bu) 2 P)]PdCl} 2 TBAF, THF/CN 10 mol % Pd 2 (dba) TBAF, THF R2 参考文献 15. Hatanaka, Y.; Hiyama, T.; J. rg. Chem., 1988; 53, Denmark, S. E.; Regens, C. S.; Acc. Chem. Res., 2008, 41, Murata, Miki; Shimazaki, Ryuta; Watanabe, Shinji; Masuda, Yuzuru.; Synthesis, 2001, 15, Manoso, Amy S.; Ahn, Chuljin; Soheili, Arash; Handy, Christopher J.; Correia, Reuben; Seganish, W. Michael; DeShong, Philip; J. rg. Chem, 2004, 69, Manoso, Amy S.; DeShong, Philip; J. rg. Chem, 2001, 66, Lee, Hon Man; Nolan, Steven P.; rg. Lett., 2000, 2, Wolf, Christian; Lerebours, Rachel; Tanzini, Elizabeth H.; Synthesis, 2003, 13, Correia, Reuben; DeShong, Philip; J. rg. Chem, 2001, 66,

6 近来, 在纳米钯 (Pd) 的作用下, 苄基卤化物和芳基三烷氧基硅烷发生高效的 Hiyama 偶联反应, 这个反应适用于多种官能团, 能够生成不同种类的二芳基甲烷 23, 并且产率较高 制备合成纳米钯不需要昂贵的配体, 只需将 K 2 PdCl 4 [19512] 和 PEG-600[19224] 在 70 搅拌 15 分钟就可以得到, 其中 PEG 在反应中即是还原剂也是稳定剂 or X + R2 (R) 3 K2PdCl4 PEG-600 TBAF in THF, 70 C or R2 X X= Cl, Br, Ts R=, Et R2 在常温或者微波加热的条件下, 乙烯基三甲氧基硅烷 [43306] 乙烯基三乙氧基硅烷 [17461] 以及乙烯基三 (2 - 甲氧基乙氧基 ) 硅烷 [25051], 在氢氧化钠溶液中与芳基卤化物反应, 生成苯乙烯其产率较高 Pd(Ac)2[19518] 在反应中作为 Pb 纳米粒子 Pd 来源, 纳米粒子 Pd 的浓度大约在 0.1mol% R X (R) 3 R Pd(Ac) 2, NaH, water X= Br, I heat or MW R= C,, Bn, Cl, Yields 70-98% 二甲基硅醇 芳基二甲基硅醇和烯基二甲基硅醇可以通过杂环化合物金属化来制备, 或者芳基或烯基卤化物发生金属 - 卤素交换反应, 随后用六甲基环三硅氧烷 - 八甲基环四硅氧烷 [21646] 或者二氯二甲基硅烷 [11331] 淬火 Denmark 等人研究发现, 在 Pd2(dba)3. CHCl3[36934] 存在的条件下, 杂芳基二甲基硅醇与芳基碘化物能够进行高效的交叉偶联反应 由于在 C-2 处的亲核性减弱,Boc- 保护的二甲基 (2 - 吲哚基 ) 硅烷醇非常难进行交叉偶联反应 他们研究发现, 在碘化铜和叔丁醇钠存在时, 用金属 Pb 作为催化剂, 硅烷醇与芳基碘进行交叉偶联反应 这个方法可以扩展到噻吩, 呋喃以及吡咯等亲核试剂与缺电子或者富电子的芳基碘的交叉偶联反应 N boc N i) LDA, 2 Cl 2, THF, 0 C, 18h ii) sat. NaHC 3 i) n-buli, Et 2, reflux, 5h ii) 71% 57% H N boc H N R NaH or NatBu /CuI Pd 2 (dba) 3. CHCl 3 (5 mol %) toluene I N boc N Yields 70-85% R R 参考文献 23. Srimani, Dipankar; Bej, Ansuman; Sarkar, Amitabha; J. rg. Chem, 2010, 75, Alacid, Emilio; Najera, Carmen; J. rg. Chem, 2008, 73, Denmark, Scott E.; Baird, John D.; Regens, Christopher S.; J. rg. Chem, 2008, 73,

7 烯丙基甲硅烷用于稳定 α- 碳负离子和 β- 碳正离子 硅原子的电子性质比碳原子更显正电性, 硅原子会对 α 位和 β 位碳原子产生相当大的电子效应 α 位被激活的硅烷能够 形成稳定的碳负离子, 从而能够提高其金属化反应以及与随后的与亲电试剂再反应性即反应活性 乙烯基, 芳基, 烯丙基以及 炔基硅烷中的稳定 β 碳正离子, 可以发生亲电取代反应, 其中, 硅基基团是离去基团 在有机合成中, 烯丙基硅烷是 很有效的中间产物, 因为其中的硅 能够稳定 α- 碳负离子和 β- 碳正离 子 26 E Elimination E + stabilised -cation E + BuLi (-) stabilised -anion E + E 通过烯丙基金属硅烷化能够直接制备简单的烯丙基硅烷, 但比较复杂的化合物体系需要采用其它的方法 [30741] Br i) Mg ii) 3 Cl 在合成三环核心的 neoliacinic 酸时 27, 需要通过烯丙基硅烷 (A) 引入侧链有机铈试剂和酯 [43618] 反应可以得到加成两个 TMSCH 2 δ- 的产物, 其中的有机铈是通过三甲基硅甲基氯化镁 [37746] 与无水氯化铈 ( 三价 ) 反应合成的 后处理之后, 三级醇经过硅胶处理更易于进行 Peterson 消除反应, 从而能够提供需要的烯丙基硅烷 H [43618] R' i) TIPS-Cl [22126] TIPS ii) MgCl [37746] CeCl 3, THF, -78 o C TIPS H 2 Peterson Elimination (A) TES H TES H H H H Tricyclic core of neoliacinic acid TIPS 在路易斯酸存在条件下, 烯丙基硅烷和不同的亲电试剂发生定向反应生成烯丙基产物 在 TMSTF[20944] 催化作用下 28,(3- 甲基环己 -1- 烯基甲基 ) 三甲基硅烷 [33904] 与 1,1- 乙醛缩二乙醇 [10222] 反应生成外消旋的烯丙基产物, 其产率高达 79% Electrophilic addition Et + + Et Et -silyl cation 3 TMSTf DCM, -75 C 3hours Et Elimination 参考文献 26. Thomas, S. E.; rganic Synthesis. The Roles of Boron and licon. xford Uni. Press, Clark, J. S.; Baxter, C. A., Dossetter, A.; Poigny, S.; Castro, J. L.; Whittingham, W. G.; J. rg. Chem., 2008, 73, Polla, M; Frejd, T.; Acta Chemica Scandinavica, 1993, 47,

8 ACRS RGANICS 有机硅烷 产品描述 货号与规格 CAS 纯度 Allyl(chloromethyl)dimethylsilane sum of isomers , 1 g; , 5 g % Allyl(diisopropyl)(4-methoxyphenyl)silane M01086DA, 1 g % Allyltrichlorosilane , 5 g; , 25 g % Allyltrimethoxysilane , 5 ml; , 25 ml % Allyltrimethylsilane , 10 ml; , 50 ml; , 250 ml % Allyltrimethylsilane , 10 ml; , 50 ml % 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane tech , 25 ml; , 100 ml; , 500 ml Aminopropyldimethylmethoxysilane , 1 g; , 5 g % 3-Aminopropyltriethoxysilane , 5 g; , 100 g; , 500 g; , 2.5 kg % 3-Aminopropyltriethoxysilane AcroSeal , 100 ml; , 800 ml % 3-Aminopropyltrimethoxysilane , 100 ml; , 500 ml % Azidotrimethylsilane , 10 ml; , 50 ml; , 250 ml % BDCS silylation reagent, AcroSeal , 100 ml; , 800 ml N-Benzyl-3-(tert-butyldimethylsilanyloxymethyl)piperid-4-one M07912DA, 1 g; M07912DE, 5 g % Benzyloxytrimethylsilane , 5 g; , 25 g; , 100 g % 1,2-Bis(chlorodimethylsilyl)ethane , 5 g; , 25 g % Bis(1H-inden-1-yl)dimethylsilane , 1 g; , 5 g % Bis(2,3,4,5-tetramethyl-2,4-cyclopentadiene-1-yl)dimethylsilane , 100 mg; , 500 mg % 1,1-Bis(trichlorosilylmethyl)ethylene , 1 g; , 5 g N,-Bis(trimethylsilyl)acetamide , 25 ml; , 100 ml; , 1 L % Bis(trimethylsilyl)acetylene , 10 g; , 50 g % Bis(trimethylsilyl)-N-tert-butylacetaldimine , 1 g % alpha,alpha-bis(trimethylsilyl)-tert-butylketimine , 500 mg Bis(trimethylsilyl)carbodiimide , 1 g; , 5 g; , 25 g % 1,4-Bis[(trimethylsilyl)ethynyl]benzene , 1 g; , 5 g % N,-Bis(trimethylsilyl)hydroxylamine , 1 g; , 5 g; , 25 g % Bis(trimethylsilyl) malonate , 10 g; , 50 g % 1,1-Bis(trimethylsilyloxy)-1,3-butadiene , 1 g ,2-Bis(trimethylsilyloxy)ethane , 10 g; , 50 g % beta,beta-bis(trimethylsilyloxy)styrene , 1 g Bis(trimethylsilyl)sulfide , 1 g; , 5 g; , 25 g % Bis(trimethylsilyl)telluride , 5 ml % N,-Bis(trimethylsilyl)trifluoroacetamide , 5 g; , 25 g; , 100 g; , 500 g % N,-Bis(trimethylsilyl)trifluoroacetamide packaged in 1 ml ampoules , 10 ml % N,-Bis(trimethylsilyl)trifluoroacetamide with 1% trimethylsilyl chloride , 25 g; , 100 g; , 500 g N-BC-2-trimethylsilylindole , 1 g; , 5 g % (2-Bromoethoxy)-tert-butyldimethylsilane , 1 g; , 10 g % 8

9 产品描述 货号与规格 CAS 纯度 (Bromomethyl)chlorodimethylsilane , 5 g; , 25 g % (4-Bromophenoxy)-tert-butyldimethylsilane , 5 ml; , 25 ml % (3-Bromophenoxy)triisopropylsilane M07899DA, 1 g % (3-Bromopropoxy)-tert-butyldimethylsilane stabilized over sodium carbonate , 1 ml; , 5 ml; , 25 ml % Bromotriethylsilane , 5 ml; , 25 ml % 4-Bromo-1-(triisopropylsilyl)-1H-indole CC39510CB, 250 mg; CC39510DA, 1 g; CC39510DE, 5 g % 5-Bromo-1-(triisopropylsilyl)-1H-indole M00980DA, 1 g; M00980EA, 10 g % Bromotrimethylsilane , 5 g; , 25 g; , 100 g; , 500 g % Bromotrimethylsilane AcroSeal , 100 ml % tert-butylchlorodimethylsilane , 5 g; , 25 g; , 100 g; , 500 g % tert-butylchlorodimethylsilane 1.0M solution in dichloromethane, AcroSeal , 100 ml tert-butylchlorodiphenylsilane , 10 g; , 50 g; , 250 g % tert-butylchlorodiphenylsilane AcroSeal , 100 ml % n-butyldimethylchlorosilane , 10 ml; , 50 ml % (tert-butyldimethylsiloxy)acetaldehyde , 1 g; , 5 g % (tert-butyldimethylsilyl)acetylene , 1 g; , 5 g % (4R)-N-(tert-Butyldimethylsilyl)azetidin-2-one-4-carboxylic acid , 1 g; , 5 g % (4S)-N-(tert-Butyldimethylsilyl)azetidin-2-one-4-carboxylic acid , 250 mg; , 1 g % tert-butyldimethylsilyl chloride 50 wt.% solution in toluene, AcroSeal , 100 ml (tert-Butyldimethylsilyl)-1H-indol-6-ylboronic acid , 1 g % N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide , 1 g; , 5 g; , 25 g % 4-(tert-Butyldimethylsilyloxy)cyclohexanone , 5 g % 3-(tert-Butyldimethylsilyloxy)phenylboronic acid , 1 g; , 5 g % 1-(tert-Butyldimethylsilyloxy)-2-propanone , 5 ml; , 25 ml % tert-butyldimethylsilyl trifluoromethanesulfonate , 5 ml; , 25 ml % Butyltrichlorosilane , 25 ml % (3-Butynyloxy)trimethylsilane , 1 g; , 5 g % 2-Carbomethoxyethyldimethoxymethylsilane , 1 g; , 5 g Chloro(chloromethyl)dimethylsilane AcroSeal , 100 ml % Chlorodiethylisopropylsilane , 25 ml % Chlorodiisopropylsilane , 5 g % Chlorodimethylethylsilane , 5 g; , 25 g % Chlorodimethylphenylsilane , 5 g; , 25 g; , 100 g % Chlorodimethylsilane , 10 g; , 50 g; , 250 g % Chlorodimethylthexylsilane , 5 g; , 25 g; , 100 g % (Chloromethyl)trichlorosilane , 5 g; , 25 g % Chloromethyltrimethylsilane , 25 g; , 100 g % 9

10 产品描述货号与规格 CAS 纯度 (3-Chloropropyl)triethoxysilane , 5 g; , 25 g; , 1 kg % (3-Chloropropyl)trimethoxysilane , 25 ml; , 100 ml; , 500 ml % 2-(4-Chlorosulfonylphenyl)ethyltrimethoxysilane 50% solution in dichloromethane , 5 g; , 25 g (4-Chlorosulfonylphenyl)ethyltrimethoxysilane 50% solution in dichloromethane, AcroSeal , 100 ml Chlorotriethylsilane , 5 ml; , 25 ml; , 100 ml; , 500 ml % Chlorotriethylsilane 1M solution in THF, AcroSeal , 100 ml Chlorotriisopropylsilane , 10 g; , 50 g; , 250 g % Chlorotriisopropylsilane , 25 g; , 100 g % Chlorotrimethylsilane , 25 ml; , 100 ml; , 250 ml; , 1 L % Chlorotrimethylsilane AcroSeal , 100 ml % Chlorotrimethylsilane 1M solution in dichloromethane, AcroSeal , 100 ml; , 800 ml Chlorotrimethylsilane 1M solution in THF, AcroSeal , 100 ml; , 800 ml Chlorotriphenylsilane , 25 g; , 100 g % Chlorotripropylsilane , 5 g; , 25 g % 3-Cyanopropyldimethylchlorosilane , 10 ml; , 50 ml % Cyanopropylmethyldichlorosilane , 5 ml; , 25 ml % 3-Cyanopropyltrichlorosilane , 25 ml; , 100 ml % Cyclohexylmethyldichlorosilane , 10 ml; , 50 ml % Cyclopentadienyltrimethylsilane , 1 g Cyclopropyl(trimethylsilyl)acetylene , 1 g; , 5 g % Decyldimethylchlorosilane , 5 ml; , 25 ml % Diacetoxydimethylsilane , 25 g % Di-tert-Butylchlorosilane , 1 g; , 5 g; , 25 g % Dichloro(chloromethyl)methylsilane , 25 g; , 100 g % Dichlorodiethylsilane , 5 g; , 25 g % Dichlorodimethylsilane , 5 ml; , 250 ml; , 1 L; , 2.5 L % Dichloromethylsilane AcroSeal , 100 ml; , 800 ml % Dichlorodiphenylsilane , 100 ml; , 500 ml; , 2.5 L % Dichlorophenylsilane AcroSeal , 100 ml; , 800 ml % Dichloromethylphenylsilane , 10 ml; , 100 ml; ml % Dichloromethylsilane , 100 ml; , 500 ml; L % Dichloromethylsilane AcroSeal , 100 ml; , 800 ml % Dichloromethylvinylsilane , 10 g; , 100 g; , 500 g; , 2.5 kg % Dichlorophenylsilane , 25 ml % 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane , 5 ml; , 25 ml % Diethoxydimethylsilane , 100 ml; , 500 ml % N,N-Diethyl-1,1,1-trimethylsilylamine , 5 g; , 25 g; , 100 g % 10

11 产品描述 货号与规格 CAS 纯度 Diiodosilane , 1 g; , 5 g Diisopropyldichlorosilane , 5 g; , 25 g % Dimethoxydimethylsilane AcroSeal , 100 ml; , 1 L % (3,3-Dimethylcyclohex-1-enylmethyl)trimethylsilane , 1 g % Dimethyldi-2-thienylsilane , 1 g; , 5 g % Dimethylethoxysilane , 5 g; , 25 g; , 100 g % Dimethylmethoxychlorosilane , 10 ml Dimethyloctadecyl[3-(trimethoxysilyl)propyl]ammonium chloride 60% in methanol , 100 ml Dimethylphenylsilane , 5 g % Dimethylphenylsilanol , 1 g; , 5 g % 1,3-Dimethyl-1,1,3,3-tetravinyldisiloxane , 1 g % Dimethyl (p-tolyl)silanol , 1 g; , 5 g % N,N-Dimethyltrimethylsilylamine , 10 ml; , 50 ml % Dimethylvinylchlorosilane , 5 g; , 25 g % 2-(Diphenylphosphino)ethyltriethoxysilane , 1 g; , 5 g; , 25 g % Diphenylsilane , 5 g; , 25 g % Diphenyltetramethyldisilane , 1 g % Divinyltetramethyldisiloxane , 10 g; , 50 g; , 250 g % Dodecyldimethylchlorosilane , 25 ml; , 100 ml % (1-Ethoxycyclopropoxy)trimethylsilane , 5 g; , 25 g; , 100 g % Ethoxytrimethylsilane , 5 g; , 25 g; , 100 g % Ethylmethyldichlorosilane , 25 ml % (Ethylthio)trimethylsilane , 1 g; , 10 g % Ethyltrichlorosilane AcroSeal , 1 L % Ethyltrimethoxysilane AcroSeal , 100 ml; , 1 L % Ethyl 3-(trimethylsilyl)propiolate , 1 g; , 25 g % Fluorodimethylphenylsilane , 1 g; , 5 g % Fluorodiphenylmethylsilane , 1 g; , 5 g % 3-Glycidoxypropyltrimethoxysilane , 5 g; , 100 g; , 500 g; , 2.5 kg % Hexakis-6-(dimethyl-tert-butylsilyl)-alpha-cyclodextrin , 1 g % Hexamethylcyclotrisiloxane , 25 g; , 100 g % Hexamethyldisilane , 10 ml; , 50 ml; , 250 ml % 1,1,1,3,3,3-Hexamethyldisilazane , 10 ml; , 100 ml; , 500 ml; , 2.5 L % 1,1,1,3,3,3-Hexamethyldisilazane AcroSeal , 100 ml % Hexamethyldisiloxane , 10 ml; , 100 ml; , 500 ml; , 2.5 L % 1,1,3,3,5,5-Hexamethyltrisiloxane , 5 ml; , 25 ml % 1,1,3,3,5,5-Hexamethyltrisiloxane AcroSeal , 100 ml % (Iodomethyl)trimethylsilane , 5 ml; , 25 ml % 11

12 产品描述货号与规格 CAS 纯度 Iodotrimethylsilane stabilized , 5 ml; , 25 ml; , 100 ml % Iodotrimethylsilane stabilized, AcroSeal , 100 ml % (3-Isocyanatopropyl)triethoxysilane , 25 g; , 100 g % Isopropyldimethylchlorosilane , 25 g % Lithium bis(trimethylsilyl)amide , 10 g; , 50 g; , 250 g % Lithium bis(trimethylsilyl)amide 0.9M solution in methylcyclohexane, AcroSeal , 100 ml; , 800 ml Lithium bis(trimethylsilyl)amide 1.0M sol. in methyl tert-butyl ether, AcroSeal , 100 ml; , 800 ml Lithium bis(trimethylsilyl)amide 1M solution in THF/Ethylbenzene, AcroSeal , 100 ml; , 800 ml Lithium (trimethylsilyl)acetylide 0.5M solution in THF, AcroSeal , 100 ml; , 800 ml (3-rcaptopropyl)trimethoxysilane tech , 50 g; , 250 g % thoxy(4-methoxyphenyl)dimethylsilane , 1 g; , 5 g % N-(thoxymethyl)-N-(trimethylsilylmethyl)benzylamine , 5 g; , 25 g % thoxytrimethylsilane , 25 g; , 100 g; , 250 g % 1-thoxy-3-(trimethylsilyloxy)-1,3-butadiene , 5 g % thyl (S)-(-)-4-bromo-3-tert-butyldimethylsilyloxybutanoate , 250 mg % thyldiethoxysilane , 5 g; , 25 g; , 100 g % thylphenylvinylsilane , 5 g % thylpropyldichlorosilane , 25 ml % thyltriallylsilane , 1 g % thyltrichlorosilane , 10 ml; , 500 ml; , 2.5 L % thyltriethoxysilane , 25 ml; , 250 ml % thyltrimethoxysilane , 5 ml; , 50 ml; , 250 ml; , 1 L % thyltrimethoxysilane AcroSeal , 100 ml; , 1 L % N-thyl-N-(trimethylsilyl)acetamide , 1 g; , 10 g % thyl (trimethylsilyl)acetate , 5 g % N-thyl-N-(trimethylsilyl)trifluoroacetamide , 5 g; , 25 g; , 100 g % 4-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate , 5 g; , 25 g % ctadecyltrichlorosilane , 25 ml; , 100 ml; , 500 ml % ctadecyltrimethoxysilane tech , 25 ml; , 100 ml % ctamethylcyclotetrasiloxane , 25 g; , 100 g; , 500 g % ctylmethyldichlorosilane , 25 ml % ctyltrichlorosilane , 100 g; , 500 g % n-ctyltriethoxysilane , 25 ml; , 100 ml % 1,1,3,5,5-Pentaphenyl-1,3,5-trimethyltrisiloxane , 500 ml Pentyltrichlorosilane , 50 g Phenethyltrichlorosilane , 1 g % Phenoxytrimethylsilane , 5 ml; , 25 ml % Phenylsilane , 5 ml; , 25 ml; , 100 ml % 12

13 产品描述货号与规格 CAS 纯度 Phenyltrichlorosilane , 10 ml; , 250 ml; , 1 L % Phenyltriethoxysilane , 250 g; , 1 kg % Phenyltrimethoxysilane , 50 ml; , 250 ml; , 1 L % Poly(dimethylsiloxane) , 250 g; , 500 g; , 2.5 kg Polymethylhydrosiloxane , 100 g; , 500 g Potassium bis(trimethylsilyl)amide 0.7M (15 wt.%) solution in toluene, AcroSeal ,800 ml Potassium trimethylsilanolate , 25 g; , 100 g % Propargyloxytrimethylsilane , 2.5 g; , 10 g % Propargyltrimethylsilane stabilized , 1 g; , 5 g % n-propyltrichlorosilane , 100 ml; , 1 L % licon(iv) chloride , 50 ml; , 500 ml; , 2.5 L % licon(iv) chloride 1M solution in methylene chloride, AcroSeal , 100 ml Sodium bis(trimethylsilyl)amide , 5 g; , 25 g; , 100 g % Sodium bis(trimethylsilyl)amide 2M solution in THF, AcroSeal , 100 ml; , 800 ml Tetraallylsilane , 1 g % Tetrabutyl orthosilicate , 5 g; , 25 g % Tetraethyl orthosilicate , 100 ml; , 250 ml; , 1 L; , 2.5 L % Tetraethyl orthosilicate AcroSeal , 100 ml; , 1 L [4 -(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]trimethylsilane , 1 g; , 5 g 98+% 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1Hindole 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1Hindole CC39539CB, 250 mg; CC39539DA, 1 g % M00983CB, 250 mg; M00983DA, 1 g % 1,1,3,3-Tetramethyldisiloxane , 25 ml; , 100 ml; , 500 ml % Tetramethyl orthosilicate , 25 g; , 100 g; , 500 g; , 2.5 kg % Tetramethylsilane NMR gade , 25 g; , 100 g % Tetramethylsilane , 100 ml; , 500 ml; , 2.5 L % Tetramethylsilane AcroSeal , 100 ml % N-TIPS indole-3-boronic acid pinacol ester , 1 g; , 5 g % N-TIPS pyrrole-3-boronic acid pinacol ester , 1 g; , 5 g % p-tolyltrimethylsilane , 1 g; , 5 g % Triethoxysilane , 10 g; , 50 g % Triethoxyvinylsilane , 25 g; , 500 g % Triethylsilane , 5 g; , 25 g; , 100 g; , 500 g % Triethylsilanol , 1 ml % 5-Triethylsilyl-4-pentyn-1-ol , 5 g % Triethylsilyl trifluoromethanesulfonate , 10 g; , 50 g % Triethylvinylsilane , 5 g % 13

14 产品描述货号与规格 CAS 纯度 (Trifluoromethyl)trimethylsilane , 1 ml; , 5 ml; , 25 ml % (Trifluoromethyl)trimethylsilane 0.5M solution in THF , 5 ml; , 25 ml; , 100 ml (Trifluoromethyl)trimethylsilane 0.5M solution in THF, AcroSeal , 100 ml (3,3,3-Trifluoropropyl)chlorodimethylsilane , 5 g; , 25 g % Triisopropylsilane , 10 g; , 50 g; , 250 g % Triisopropylsilane , 10 g; , 50 g % (Triisopropylsilyl)acetylene , 5 g; , 25 g % Triisopropylsilyl-trifluoromethanesulfonate , 10 g % Trimethoxysilane , 5 g; , 25 g; , 100 g % 3-(Trimethoxysilyl)propyl acrylate stabilized , 5 g % N-[3-(Trimethoxysilyl)propyl]ethylenediamine , 100 g; , 500 g % 3-(Trimethoxysilyl)propyl methacrylate , 5 ml; , 100 ml; , 500 ml % N-(Trimethylsilyl)acetamide , 25 g; , 100 g % Trimethylsilyl acetate , 25 g; , 100 g % (Trimethylsilyl)acetonitrile , 1 g; , 5 g % Trimethylsilylacetylene , 5 g; , 25 g; , 100 g % N-(Trimethylsilyl)allylamine , 1 g; , 5 g % 2-Trimethylsilylanisole , 1 g; , 5 g % 3-Trimethylsilylanisole , 1 g; , 5 g % 4-Trimethylsilylanisole , 1 g; , 5 g % 1-(Trimethylsilyl)-1H-benzotriazole , 1 g; , 5 g % Trimethylsilyl bromoacetate , 5 g % 2-Trimethylsilyl-N-tert-butylacetaldimine , 1 g Trimethylsilyl-N-tert-butyl-2,4-hexadienaldimine , 250 mg Trimethylsilyl-3-butyn-1-ol , 5 g % Trimethylsilyl cyanide , 500 g % (Trimethylsilyl)diazomethane approx. 2M solution in diethyl ether , 5 ml; , 25 ml; , 100 ml (Trimethylsilyl)diazomethane approx. 2M solution in diethyl ether, AcroSeal , 100 ml (Trimethylsilyl)diazomethane ca. 2.0M solution in hexanes, tech , 5 ml; , 25 ml; , 100 ml; , 500 ml (Trimethylsilyl)diazomethane approx. 2.0M solution in hexanes, AcroSeal , 100 ml;, Trimethylsilyl diethylphosphonoacetate , 1 ml; , 5 ml; , 25 ml % Trimethylsilyl 3,3-dimethylacrylate , 1 g (Trimethylsilyl)ethanol , 10 ml; , 50 ml; , 250 ml % 2-(Trimethylsilyl)ethoxymethyl chloride tech., stabilized , 5 ml; , 25 ml; , 100 ml % -(Trimethylsilyl)hydroxylamine , 1 g; , 5 g % N-(Trimethylsilyl)imidazole , 25 g; , 100 g; , 250 g % Trimethylsilyl isocyanate , 5 g; , 25 g % Trimethylsilyl isothiocyanate , 10 g; , 50 g % Trimethylsilyl methacrylate stabilized , 5 g % 14

15 产品描述货号与规格 CAS 纯度 Trimethylsilylmethyl acetate , 5 g % 2-(Trimethylsilylmethyl)allyl acetate , 1 g; , 5 g; , 25 g % (Trimethylsilyl)methyllithium 0.7M (10 wt%) solution in hexanes, AcroSeal , 100 ml; , 800 ml (Trimethylsilyl)methylmagnesium chloride 1.3M solution in THF, AcroSeal , 100 ml; , 800 ml (Trimethylsilyl)methyl trifluoromethanesulfonate , 5 g % 4-(Trimethylsilyl)morpholine , 5 g; , 25 g % 3-(Trimethylsilyloxy)-1-butyne , 5 g; , 25 g % 5-Trimethylsilyl-4-pentyn-1-ol , 5 g; , 25 g % 3-(Trimethylsilyl)-1-propanol , 5 g % 3-Trimethylsilylpropargyl aldehyde diethyl acetal , 1 g; , 5 g % 3-(Trimethylsilyl)propargyl bromide , 1 g; , 5 g % 3-(Trimethylsilyl)propionic acid-d4 sodium salt , 1 g atom% D 1-(Trimethylsilyl)-1-propyne , 1 g; , 5 g % 3-Trimethylsilyl-2-propyn-1-ol , 1 g % 2-(Trimethylsilyl)pyridine , 1 g; , 10 g % 2-(Trimethylsilyl)thiazole , 1 ml; , 5 ml; , 25 ml % Trimethylsilyl trifluoromethanesulfonate , 10 ml; , 50 ml; , 250 ml % Trimethylstannylbutyldimethylsilane , 1 g % Trimethylstannyldimethylphenylsilan , 5 g % Trimethylstannylmethyldiphenylsilan , 1 g % Trimethyl-2-thienylsilane , 5 g % Trimethyl(2-thienyl)silane AC30828EA, 10 g % Trioctylsilane , 5 g; , 25 g % Tri-n-propylsilane , 5 g; , 25 g % Tris[N,N-bis(trimethylsilyl)amide]erbium(III) , 1 g % Tris(trimethylsilyl)amine , 5 g; , 25 g % Tris(trimethylsilyl) borate , 25 g; , 100 g Tris(trimethylsilyloxy)ethylene , 1 g; , 5 g; , 25 g % Tris(trimethylsilyloxy)silane , 5 g; , 25 g % Tris(trimethylsilyl) phosphite , 5 g; , 25 g % Tris(trimethylsilyl)silane , 2.5 ml; , 25 ml % Vinyloxytrimethylsilane , 1 g; , 5 g % Vinyltrimethoxysilane , 100 g; , 500 g % Vinyltrimethoxysilane AcroSeal , 100 ml; , 1 L % Vinyltrimethylsilane , 25 ml; , 100 ml % Vinyl tris(2-methoxyethoxy) silane , 10 ml; , 100 ml % Vinyltris(trimethylsilyloxy)silane , 1 ml % 15

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