1,2-双(三甲基硅烷基)苯 | 17151-09-6

• 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: 1,2-双(三甲基硅烷基)苯
• 中文别名: 1,2-双(三甲基硅)苯
• 英文名称: 1,2-bis(trimethylsilyl)benzene
• 英文别名: 1,2-Bis(trimethylsilyl)benzol；o-Bis-(trimethylsilyl)-benzol；o-bis(trimethylsilyl)benzene；bis(o-trimethylsilyl)benzene；trimethyl-(2-trimethylsilylphenyl)silane
• CAS: 17151-09-6
• 化学式: C₁₂H₂₂Si₂
• mdl: MFCD00015590
• 分子量: 222.478
• InChiKey: YHMJZIJXVNRXIN-UHFFFAOYSA-N

物化性质

• 沸点：
  115 °C (10 mmHg)
• 密度：
  0.91

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090
• 安全说明：
  S24/25
• 储存条件：
  存储条件为0-10°C，并需置于惰性气体中，避免与空气接触及加热。

SDS

Name:	1 2-Bis(trimethylsilyl)benzene 98% Material Safety Data Sheet
Synonym:	None
CAS:	17151-09-6

Section 1 - Chemical Product MSDS Name:1 2-Bis(trimethylsilyl)benzene 98% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17151-09-6	1,2-Bis(trimethylsilyl)benzene	98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 17151-09-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear light yellow
Odor: benzene-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 115 deg C @ 10 mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H22Si2
Molecular Weight: 222.48

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, silicon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17151-09-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2-Bis(trimethylsilyl)benzene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 17151-09-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17151-09-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17151-09-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,2-双(三甲基硅烷基)苯 在 溴 、 一溴化碘 作用下， 生成 邻碘溴苯
  参考文献：
  名称：

  Felix,G. et al., Angewandte Chemie, 1977, vol. 89, p. 502 - 504

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-bis(trimethylsilyl)cyclohexa-1,4-diene 反应 2.0h， 以90%的产率得到1,2-双(三甲基硅烷基)苯
  参考文献：
  名称：

  钛催化的共轭二烯与双（三甲基甲硅烷基）乙炔的Diels-Alder环加成反应。1,2-双（三甲基硅烷基）环己-1,4-二烯，1,2-双（三甲基硅烷基）苯及其甲基衍生物

  摘要：

  催化体系Et 2 AlCl / TiCl 4诱导双（三甲基甲硅烷基）乙炔的Diels-Alder环加成反应成1,3-丁二烯，异戊二烯，2,3-二甲基-1,3-丁二烯和（E）-1,3-戊二烯以高收率得到1,2-双（三甲基磺酰基）环己-1,4-二烯。在加热至240℃时，环己二烯易于转化为相应的1，2-双（三甲基甲硅烷基）苯。报告并简要讨论了所有所得产物的质谱，红外，1 H，13 C和29 Si NMR光谱。芳香族化合物的拥挤特征反映在其质量，13 C和29 Si NMR光谱中。

  DOI：

  10.1016/0022-328x(85)87410-6
• 作为试剂：
  描述：

  二正戊基酮 在 二甲氨基三氟化硫 、 4,4'-二叔丁基苯并 、 1,2-双(三甲基硅烷基)苯 、 lithium 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 6-butylundecane
  参考文献：
  名称：

  氟代烷烃的还原脱氟

  摘要：

  在亚化学计量的1,2-双（三甲基甲硅烷基）苯1的存在下，过量的锂粉和催化量的DTBB与伯，仲和叔氟烷烃反应，得到相应的烷烃，这是由氟-氢交换产生的。该方法可以扩展到非二元的二氟化物。还研究了二甲硅烷基化的化合物在萘催化的氟苯和苄基氟化物的锂化反应中的作用。

  DOI：

  10.1016/s0040-4020(03)00019-x

文献信息

• Halogen−Metal Exchange in 1,2-Dibromobenzene and the Possible Intermediacy of 1,2-Dilithiobenzene
  作者：Holger F. Bettinger、Matthias Filthaus

  DOI：10.1021/jo7013033

  日期：2007.12.1

  The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine−lithium exchange and subsequent

  报道了使用叔丁基锂和三甲基甲硅烷基磺酸盐由1，2-二溴苯一步一步高产率合成1，2-双（三甲基甲硅烷基）苯。机理研究表明1，2-二硫代苯不是该反应的中间体。三甲基甲硅烷基三氟甲基磺酸盐和叔丁基锂在非常低的温度下共存，可以进行一系列的溴-锂交换和随后的衍生化反应。
• Lewis Acid Directed Regioselective Metalations of Pyridazine
  作者：Moritz Balkenhohl、Harish Jangra、Tobias Lenz、Marian Ebeling、Hendrik Zipse、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1002/anie.201903839

  日期：2019.7

  Mono‐ or bidentate boron Lewis acids trigger a regioselective magnesiation or zincation of pyridazine in position C3 (ortho product) or C4 (meta product). The regioselectivity of the metalation was rationalized with the help of calculated pKa values of both pyridazine and pyridazine/Lewis acid complexes.

  单或二齿硼路易斯酸在位置C3（邻位产物）或C4（间位产物）处引发哒嗪的区域选择性镁化或锌化。借助于计算的哒嗪和哒嗪/路易斯酸络合物的p K a值，使金属化的区域选择性合理化。
• (Phenyl)[o-(trimethylsilyl)phenyl]iodonium triflate. A new and efficient precursor of benzyne
  作者：Tsugio Kitamura、Masakatsu Yamane

  DOI：10.1039/c39950000983

  日期：——

  (Phenyl)[o-(trimethylsilyl)phenyl]iodonium triflate readily prepared from o-bis(trimethylsilyl)benzene and the hypervalent iodine(III) reagent [Phl(OAc)2·2TfOH] shows excellent formation of benzyne under mild and neutral conditions and efficiently provides adducts with typical trapping agents, e.g. furan, anthracene, diphenylisobenzofuran and tetraphenylcyclopentadienone.

  (Phenyl)[o-(trimethylsilyl)phenyl]碘鎓三氟甲磺酸盐，由o-双(三甲基硅基)苯与高价碘(III)试剂[PhI(OAc)2·2TfOH]制备而成，在温和中性条件下表现出优异的苯炔形成能力，并能高效地与典型的捕获剂如呋喃、蒽、二苯基异苯并呋喃及四苯基环戊二烯酮生成加合物。
• A New and Efficient Hypervalent Iodine−Benzyne Precursor, (Phenyl)[<i>o</i>-(trimethylsilyl)phenyl]iodonium Triflate:  Generation, Trapping Reaction, and Nature of Benzyne
  作者：Tsugio Kitamura、Masakatsu Yamane、Kensuke Inoue、Mitsuru Todaka、Norihiko Fukatsu、Zhaohong Meng、Yuzo Fujiwara

  DOI：10.1021/ja992324x

  日期：1999.12.1

  the reaction in the presence of furan indicates a quantitative generation of benzyne and its efficient capture by the furan. Similarly, methylbenzynes (22 and 27) are efficiently generated from the corresponding methyl-substituted (trimethylsilyl)phenyliodonium triflates (12 and 13). The preparation of the hypervalent iodine−benzyne precursors, the generation of benzynes, the trapping reactions, and

  报道了一种新的高效高价碘-苄前体，(苯基)[2-(三甲基甲硅烷基)苯基]碘鎓三氟甲磺酸盐 (10)。高价碘-苄前体 10 很容易通过 1,2-双（三甲基甲硅烷基）苯与 PhI(OAc)2/TfOH 试剂系统反应制备。在诸如呋喃、2-甲基呋喃、蒽、四苯基环戊二烯酮或 1,3-二苯基异苯并呋喃的捕集剂存在下，在室温下在 CH2Cl2 中用 Bu4NF 处理 10 可得到高产率的苯炔加合物。特别是，在呋喃存在下反应的结果表明苯的定量产生及其被呋喃有效捕获。类似地，从相应的甲基取代的（三甲基甲硅烷基）苯基碘鎓三氟甲磺酸盐（12 和 13）有效地生成甲基苄（22 和 27）。
• Tridentate Lewis-acids based on triphenylsilane
  作者：Janek Tomaschautzky、Beate Neumann、Hans-Georg Stammler、Andreas Mix、Norbert W. Mitzel

  DOI：10.1039/c6dt04293g

  日期：——

  Several derivatives of the propeller-shaped ortho-substituted triphenylsilanes, carrying metal- or silicon-based acceptor groups, are reported. They were synthesized starting from tris(2-bromophenyl)fluorosilane, tris(2-vinylphenyl)fluorosilane and tris(2-ethynylphenyl)fluorosilane to generate a scope of Lewis-acidic molecules with different cavities. An improved synthetic protocol for donor-free

  报道了带有金属或硅基受体基团的螺旋桨状邻位取代的三苯基硅烷的几种衍生物。它们是从三（2-溴苯基）氟硅烷，三（2-乙烯基苯基）氟硅烷和三（2-乙炔基苯基）氟硅烷开始合成的，以产生一定范围的具有不同空穴的路易斯酸性分子。描述了一种用于无供体的三（2-锂基苯基）硅烷的改进的合成方案。首次提出了在客体-客体化学中尝试探测三倍烷烃官能化的邻位取代的三苯基硅烷与三齿Lewis碱性客体分子之间结合的方法。报道了双马来三茂铁的结晶状态下的合成和第一分子结构测定。