三(三甲基硅烷基)硅烷醇 | 7428-60-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 三(三甲基硅烷基)硅烷醇
• 英文名称: tris(trimethylsilyl)silanol
• 英文别名: 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-ol；supersilanol；hydroxy-tris(trimethylsilyl)silane
• CAS: 7428-60-6
• 化学式: C₉H₂₈OSi₄
• 分子量: 264.663
• InChiKey: ABTWCNHNRLMBFR-UHFFFAOYSA-N

物化性质

• 沸点：
  235.1±23.0 °C(Predicted)
• 密度：
  0.833±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  室温

SDS

Version 1.0
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name TRIS(TRIMETHYLSILYL)SILANOL - 50 MG

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2 - Hazards Identification

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SPECIAL INDICATION OF HAZARDS TO HUMANS AND THE ENVIRONMENT
Not hazardous according to Directive 67/548/EEC.

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
TRIS(TRIMETHYLSILYL)SILANOL 7428-60-6 None None
Formula C9H28OSI4
Molecular Weight 264,6600 AMU

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If breathing becomes difficult,
call a physician.
AFTER SKIN CONTACT
In case of contact, immediately wash skin with soap and copious
amounts of water.
AFTER EYE CONTACT
In case of contact with eyes, flush with copious amounts of
water for at least 15 minutes. Assure adequate flushing by
separating the eyelids with fingers. Call a physician.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
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Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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METHODS FOR CLEANING UP
Absorb on sand or vermiculite and place in closed containers for
disposal. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Avoid inhalation. Avoid contact
with eyes, skin, and clothing. Avoid prolonged or repeated
exposure.
STORAGE
Conditions of Storage: Keep tightly closed.
SPECIAL REQUIREMENTS: Air and moisture sensitive.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Safety shower and eye bath. Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Respiratory protection is not required. Where
protection is desired, use multi-purpose combination (US) or type
ABEK (EN 14387) respirator cartridges.
Hand Protection: Protective gloves.
Eye Protection: Chemical safety goggles.

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9 - Physical and Chemical Properties

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Appearance Physical State: Liquid
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
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Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Stable: Stable.
Materials to Avoid: Strong oxidizing agents.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Silicon oxide, Silicon dioxide.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur

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11 - Toxicological Information

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SIGNS AND SYMPTOMS OF EXPOSURE
To the best of our knowledge, the chemical, physical, and
toxicological properties have not been thoroughly investigated.
ROUTE OF EXPOSURE
Skin Contact: May cause skin irritation.
Skin Absorption: May be harmful if absorbed through the skin.
Eye Contact: May cause eye irritation.
Inhalation: Material may be irritating to mucous membranes and
upper respiratory tract. May be harmful if inhaled.
Ingestion: May be harmful if swallowed.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Contact a licensed professional waste disposal service to dispose
of this material. Dissolve or mix the material with a combustible
solvent and burn in a chemical incinerator equipped with an
afterburner and scrubber. Observe all federal, state, and local
environmental regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
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IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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Not hazardous according to Directive 67/548/EEC.
Caution: Substance not yet fully tested (EU).

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

在双催化铜/光致氧化还原迅速发展的形势下，MacMillan实验室已证明超级硅烷醇是通过烷基卤化物和芳基卤化物的三氟甲基化大量产生烷基-CF₃和芳基-CF₃的一种极佳试剂。这两种情况下，这些反应均具有较宽的底物范围和良好的官能团耐受性。具体而言，在温和条件下，各种五元和六元杂芳基卤化物可以容易地转化为相应的三氟甲基杂芳烃。

反应信息

• 作为反应物：
  描述：

  三(三甲基硅烷基)硅烷醇 在 三甲基氯硅烷 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以90%的产率得到氯三(三甲基甲硅烷基)硅烷
  参考文献：
  名称：

  锂和三（三甲基甲硅烷基）硅烷醇钠。合成和反应性

  摘要：

  三（三甲基甲硅烷基）硅烷醇锂和钠是通过三（三甲基甲硅烷基）硅烷醇与 BunLi 或 PriONa 在己烷中的反应获得的。对于钠和锂衍生物，苯溶液中硅烷醇化物的缔合度分别为 2 和 4。(Me3Si)3SiONa 在与 Me3SiCl 的反应中明显比锂衍生物更具活性。三（三甲基甲硅烷基）硅烷醇与三甲基氯硅烷反应生成 (Me3Si)3SiCl。(Me3Si)3SiONa (Li) 在苯和己烷中水解产生相应的硅烷醇，而在 HMPA 中观察到 Si-Si 键断裂和析氢。

  DOI：

  10.1007/bf00707063
• 作为产物：
  描述：

  三(三甲基硅基)硅烷 在 水 、 三乙胺 作用下， 以 四氯化碳 、 氯仿 、 正己烷 为溶剂， 反应 28.0h， 以96.9%的产率得到三(三甲基硅烷基)硅烷醇
  参考文献：
  名称：

  早期过渡金属醇盐的三（三甲基甲硅烷基）氧化硅衍生物的合成与表征，该化合物可热转化为各种陶瓷-二氧化硅建筑材料

  摘要：

  为了生成用于生产金属硅氧化物（MSiO x）材料的单源前体，使三（三甲基硅烷基）硅烷醇（H-SST或H-OSi（SiMe 3）3（1）配体与一系列第4组和第5组金属醇盐的混合物。第4组产物的晶体学特征为[Ti（SST）2（OR）2 ]（OR = OPr i（2），OBu t（3），ONep（4））; [Ti （SST）3（OBu n）]（5）； [Zr（SST）2（OBu t）2（py）]（6）; [Zr（SST）3（OR）]（OR = OBu t（7），ONep，（8））；[Hf（SST）2（OBu t）2 ]（9）; 和[Hf（SST）2（ONep）2（py）n ]（n = 1（10），n = 2（10a））其中OPr i = OCH（CH 3）2，OBu t = OC（CH 3）3，OBu n = O（CH 2）3 CH 3，ONep ＝ OCH 2 C（CH 3）3，py ＝吡啶。

  DOI：

  10.1021/acs.inorgchem.8b00630
• 作为试剂：
  描述：

  7-溴双环[2.2.1]庚烷 、 3-氯-吲唑 在 三(三甲基硅烷基)硅烷醇 、 [Ir(dF(CF₃)-ppy)₂(4,4'dCF₃-bpy)]PF₆ 、 水 、 bis(2,2,6,6-tetramethyl-3,5-heptadionato) copper(II) 、 lithium tert-butoxide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以47%的产率得到7-(3-chloro-1H-indazol-1-yl)bicyclo[2.2.1]heptane
  参考文献：
  名称：

  通过铜金属光氧化还原和烷基卤化物的甲硅烷基自由基活化的通用 N-烷基化平台

  摘要：

  通过可见光诱导的金属光氧化还原平台实现了酰胺、磺胺、苯胺、亚胺或N-杂环与广谱电子和空间多样化烷基溴的催化结合。卤素提取-自由基捕获 (HARC) 机制的使用允许使用简单的 Cu(II) 盐在室温下耦合 C( sp 3 )-溴化物，有效绕过通常与热诱导 S N 2 或 S相关的过高障碍N 1 N-烷基化。这种区域和化学选择性方案与 >10 类药物相关的N兼容- 亲核试剂，包括已建立的药剂，以及结构多样的伯、仲和叔烷基溴。此外，通过将N-亲核试剂与环丙基溴和未活化的烷基氯（与亲核取代途径不相容的底物）结合，突出了 HARC 方法与传统惰性偶联伙伴结合的能力。初步的机械实验验证了该平台的双重催化、开壳性质，这使得在传统的基于卤化物的N-烷基化系统中无法实现的反应性成为可能。

  DOI：

  10.1016/j.chempr.2021.05.005

文献信息

• Oxidation of Triorganosilanes and Related Compounds by Chlorine Dioxide
  作者：S. A. Grabovskiy、N. N. Kabal’nova

  DOI：10.1134/s1070363221120069

  日期：2021.12

  mechanism explaining the formation of products and the observed regularities of the oxidation of silanes with chlorine dioxide has been proposed. A thermochemical analysis of some possible pathways in the gas phase using methods G4, G3, M05, and in an acetonitrile solution by the SMD-M05 method was carried out. The oxidation process can occur both with the participation of ionic and radical intermediates

  用二氧化氯氧化三乙基硅烷、叔丁基二甲基硅烷、二甲基苯基硅烷、三苯基硅烷、1,1,1,2四甲基-2-苯基二硅烷、三(三甲基甲硅烷基)硅烷、六甲基二硅烷、四(三甲基甲硅烷基)硅烷、1,1,3,3四异丙基二硅氧烷出去。研究的三有机硅烷与二氧化氯在乙腈溶液中的反应产物是相应的硅烷醇和硅氧烷。已经提出了解释产物形成和观察到的用二氧化氯氧化硅烷的规律的机制。使用方法 G4、G3、M05 对气相中的一些可能途径进行了热化学分析，并通过 SMD-M05 方法对乙腈溶液中的一些可能途径进行了热化学分析。氧化过程可以在离子和自由基中间体的参与下发生，
• Twofold Radical-Based Synthesis of <i>N</i>,<i>C</i>-Difunctionalized Bicyclo[1.1.1]pentanes
  作者：Helena D. Pickford、Jeremy Nugent、Benjamin Owen、James. J. Mousseau、Russell C. Smith、Edward A. Anderson

  DOI：10.1021/jacs.1c04180

  日期：2021.7.7

  Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs;

  双环[1.1.1] pentylamines（BCPAs）是重要性日益增加，以制药业作为藻3个苯胺和富含的bioisosters ñ -叔丁基的基团。在这里，我们报告了使用双重自由基功能化策略轻松合成 1,3-二取代 BCPA。磺胺基自由基，通过 α-碘氮丙啶的碎裂产生，经过初始添加到 [1.1.1] 丙烷中，得到碘-BCPA；然后通过甲硅烷基介导的 Giese 反应将这些产物中新形成的 C-I 键功能化。这种化学反应也可以顺利转化为 1,3-二取代碘-BCP。可容纳多种自由基受体和碘-BCPA，可直接获取一系列有价值的类苯胺等排体。
• Organophotoredox assisted cyanation of bromoarenes <i>via</i> silyl-radical-mediated bromine abstraction
  作者：Maniklal Shee、Sk. Sheriff Shah、N. D. Pradeep Singh

  DOI：10.1039/d0cc00163e

  日期：——

  The insertion of a nitrile (–CN) group into arenes through the direct functionalization of the C(sp2)–Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed

  通过C（sp 2）-Br键的直接官能化将腈基（–CN）插入芳烃中是一项具有挑战性的反应。本文中，我们报道了使用有机光氧化还原催化剂4CzIPN和甲苯磺酰氰（TsCN）作为腈源的有机光氧化还原方法，用于芳基溴化物的氰化。通过单电子转移（SET）机制，将光生甲硅烷基自由基用于从芳基溴化物中提取溴，以提供芳基基团，该芳基基团同时被TsCN拦截以提供芳族腈。已证明一系列包含给电子和吸电子基团的底物在室温下以良好的产率进行氰化。
• Highly Selective Hydroxylation and Alkoxylation of Silanes: One-Pot Silane Oxidation and Reduction of Aldehydes/Ketones
  作者：Nianhua Luo、Jianhua Liao、Lu Ouyang、Huiling Wen、Yuhong Zhong、Jitian Liu、Weiping Tang、Renshi Luo

  DOI：10.1021/acs.organomet.9b00716

  日期：2020.1.13

  An efficient chemoselective iridium-catalyzed method for the hydroxylation and alkoxylation of organosilanes to generate hydrogen gas and silanols or silyl ethers was developed. A variety of sterically hindered silanes with alkyl, aryl, and ether groups were tolerated. Furthermore, this atom-economical catalytic protocol can be used for the synthesis of silanediols and silanetriols. A one-pot silane

  开发了一种有效的化学选择性铱催化的方法，用于有机硅烷的羟基化和烷氧基化以生成氢气和硅烷醇或甲硅烷基醚。可以耐受各种具有烷基，芳基和醚基的空间位阻硅烷。此外，这种原子经济的催化方案可用于硅烷二醇和硅烷三醇的合成。还实现了一锅硅烷氧化和醛/酮的化学选择性还原。
• Cobalt-Catalyzed Selective Synthesis of Disiloxanes and Hydrodisiloxanes
  作者：Sandip Pattanaik、Chidambaram Gunanathan

  DOI：10.1021/acscatal.9b00305

  日期：2019.6.7

  independent experiments confirmed the catalytic oxidation of silane to silanol, and further dehydrocoupling processes are involved in syntheses of symmetrical siloxanes, cyclotetrasiloxanes, and siloxane cage compounds, whereas the unsymmetrical monohydrosiloxane syntheses from silanes and silanols proceeded via dehydrogenative coupling reactions. Overall these cobalt-catalyzed oxidative coupling reactions

  分别从硅烷和二氢硅烷与水的反应中获得对称的硅氧烷和环四硅氧烷的选择性合成，并且该反应由NNN H t Bu钴（II）钳形配合物催化。有趣的是，当苯硅烷用水进行催化时，获得了由12个硅和18个氧中心组成的硅氧烷笼，反应明显进行，释放出3当量的分子氢（36 H 2）在温和的实验条件下。在硅烷与不同的硅烷醇反应后，通过钴催化实现了高选择性和受控的高级单氢硅氧烷和二甲氧基单氢硅烷的合成。释放的分子氢是在所有这些转化中观察到的唯一副产物。机理研究表明，反应是通过均质途径发生的。动力学和独立实验证实了硅烷催化氧化为硅烷醇的过程，并且进一步的脱氢偶联过程还涉及对称硅氧烷，环四硅氧烷和硅氧烷笼型化合物的合成，而硅烷和硅烷醇的不对称一氢硅氧烷则通过脱氢偶联反应进行合成。总体而言，这些钴催化的氧化偶联反应基于Si–H，Si–OH，和硅烷，硅烷醇和水的O–H键活化。建议使用由Co（II）中间体组成的催化循环。