苯基三乙氧基硅烷 | 780-69-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硅烷
• 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: 苯基三乙氧基硅烷
• 中文别名: 三乙氧基苯基硅烷；苯基三乙氧基
• 英文名称: Phenyltriethoxysilan
• 英文别名: triethoxyphenylsilane；triethoxyphenylsilan；phenyltriethoxysilane；triethoxy(phenyl)silane
• CAS: 780-69-8
• 化学式: C₁₂H₂₀O₃Si
• mdl: MFCD00009065
• 分子量: 240.374
• InChiKey: JCVQKRGIASEUKR-UHFFFAOYSA-N

物化性质

• 沸点：
  112-113 °C10 mm Hg(lit.)
• 密度：
  0.996 g/mL at 25 °C(lit.)
• 蒸气密度：
  >1 (vs air)
• 闪点：
  109 °F
• LogP：
  -0.31-3.4 at 22℃
• 物理描述：
  Liquid
• 保留指数：
  1298.8
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂和水分直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  3.2
• 危险品标志：
  Xn
• 安全说明：
  S16,S24/25,S26,S37/39
• 危险类别码：
  R10,R21
• WGK Germany：
  3
• 海关编码：
  29310095
• 危险品运输编号：
  UN 1993 3/PG 3
• 危险类别：
  3.2
• RTECS号：
  VV4900000
• 包装等级：
  III
• 危险标志：
  GHS02
• 危险性描述：
  H226
• 危险性防范说明：
  P210,P260,P370+P378
• 储存条件：
  储存于干燥的惰性气体中，并保持容器密封。将其存放在阴凉、干燥处。

SDS

Name:	Phenyltriethoxysilane 98% Material Safety Data Sheet
Synonym:	Triethoxyphenylsilane
CAS:	780-69-8

Section 1 - Chemical Product MSDS Name:Phenyltriethoxysilane 98% Material Safety Data Sheet
Synonym:Triethoxyphenylsilane

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
780-69-8	Phenyltriethoxysilane	98	212-305-8

Hazard Symbols: XN
Risk Phrases: 10 21

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable. Harmful in contact with skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Ingestion of large amounts may cause CNS depression.
Inhalation:
Causes respiratory tract irritation.
Chronic:
Ethanol is mainly metabolized in the liver, which is also one of the primary target organs. While ethanol is well known to cause cirrhosis of the liver in alcoholics, liver cirrhosis has also been produced in rabbits exposed by inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid. Get medical aid immediately. 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:
Treat symptomatically and supportively.

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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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Contact with water liberates highly flammable gases.
Extinguishing Media:
Use carbon dioxide or dry chemical. Do NOT get water inside containers.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. Do not get water inside containers. A vapor suppressing foam may be used to reduce vapors.

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Section 7 - HANDLING and STORAGE
Handling:
Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Use with adequate ventilation. Do not allow contact with water. Wash clothing before reuse. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Keep from contact with moist air and steam.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Flammables-area. Store protected from moisture.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 780-69-8: Personal Protective Equipment Eyes: Wear chemical splash goggles.
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. Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 112-113 deg C @ 10 mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: 265 deg C ( 509.00 deg F)
Flash Point: 42 deg C ( 107.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Reacts.
Specific Gravity/Density: .9900 g/ml
Molecular Formula: C12H20O3Si
Molecular Weight: 240.38

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Material generates ethanol on contact with water.
Conditions to Avoid:
Ignition sources, moisture, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids, water.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, silicon dioxide, ethanol.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 780-69-8: VV4900000 LD50/LC50:
CAS# 780-69-8: Draize test, rabbit, eye: 500 mg/24H Mild; Draize test, rabbit, skin: 500 mg/24H Mild; Oral, rat: LD50 = 2830 uL/kg; Skin, rabbit: LD50 = 3180 uL/kg.
Carcinogenicity:
Phenyltriethoxysilane - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Shipping Name: FLAMMABLE LIQUID, N.O.S.*
Hazard Class: 3
UN Number: 1993
Packing Group: III
IMO
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3.3
UN Number: 1993
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE LIQUID, N.O.S.
Hazard Class: 3
UN Number: 1993
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 10 Flammable.
R 21 Harmful in contact with skin.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 780-69-8: No information available.
Canada
CAS# 780-69-8 is listed on Canada's DSL List.
CAS# 780-69-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 780-69-8 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

• 用途

  • 用于制备高分子有机硅化合物的原料；作为硅树脂的交联剂，也可用作苯基硅油、硅橡胶的原料。

• 储存条件

  • 室内避光存放，保持通风、阴凉和干燥。确保桶盖密封良好，能有效隔绝空气。

• 产品描述

  • 本品为无色透明液体，可溶于多种有机溶剂。

• 化学性质

  • 无色透明液体，气味温和。

• 用途

  • 硅类亲核试剂，具有钯催化交叉偶联反应活性。

反应信息

• 作为反应物：
  描述：

  苯基三乙氧基硅烷 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 13.0h， 生成 溴苯
  参考文献：
  名称：

  CARBON–SILICON BOND CLEAVAGE OF ORGANOTRIALKOXYSILANES AND ORGANOSILATRANES WITHm-CHLOROPERBENZOIC ACID ANDN-BROMOSUCCINIMIDE. NEW ROUTE TO PHENOLS, PRIMARY ALCOHOLS AND BROMIDES

  摘要：

  烷基和芳基三乙氧基硅烷能够顺利地通过间氯过氧苯甲酸（m-氯过氧苯甲酸）进行氧化碳硅键断裂，得到相应的醇。类似地，硅拉烷分别与m-氯过氧苯甲酸和N-溴代丁二酰亚胺反应，分别得到醇和溴化物。

  DOI：

  10.1246/cl.1981.243
• 作为产物：
  描述：

  硅酸四乙酯 在 苯基溴化镁 作用下， 以 not given 为溶剂， 生成 苯基三乙氧基硅烷
  参考文献：
  名称：

  Khotinsky, E.; Seregenkoff, B., Archives des Sciences Physiques et Naturelles, 1908, vol. 25, p. 516 - 516

  摘要：

  DOI：
• 作为试剂：
  描述：

  异丁烯 在 苯基三乙氧基硅烷 、 四氯化钛 、 乙醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 polyisobutene
  参考文献：
  名称：

  [DE] SUBSTITUIERTE CYCLOALKANE UND IHRE VERWENDUNG ALS INITIATOREN ZUR KATIONISCHEN POLYMERISATION
  [EN] SUBSTITUTED CYCLOALKANES, AND USE THEREOF AS CATIONIC POLYMERIZATION INITIATORS
  [FR] CYCLOALCANES SUBSTITUES ET LEUR UTILISATION COMME INITIATEURS POUR LA POLYMERISATION CATIONIQUE

  摘要：

  描述了取代的7至12元环烷烃，其在三级环烷碳原子上具有离去基团，特别是氯原子，以及它们的制备方法和作为阳离子聚合引发剂的用途，特别是用于异丁烯的阳离子聚合。首选化合物是1,4-二氯-1,4-二甲基环辛烷，1,5-二氯-1,5-二甲基环辛烷及其混合物。它们是通过将氯化氢加到适当取代的环烷烯烃上制备的。

  公开号：

  WO2005044766A1

文献信息

• Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone
  作者：Federica Valentini、Francesco Ferlin、Simone Lilli、Assunta Marrocchi、Liu Ping、Yanlong Gu、Luigi Vaccaro

  DOI：10.1039/d1gc01707a

  日期：——

  commercial Pd/C catalyst. The good reactivity in the biomass-derived solvent (GVL) confirms that the Pd/PiNe heterogeneous catalyst is a valid system that can be integrated into a waste valorization chain within a circular economy approach. In addition, the efficiency of the catalyst has also been extended to perform the challenging consecutive Hiyama–Heck reaction to afford differently substituted (E)-1

  在这里，我们报告了一个简单的协议，用于评估普通城市生物废物的价值。将松针城市垃圾预处理后获得的木质纤维素生物质有效地转化为用于固定 Pd 纳米颗粒的低成本载体 (PiNe)。最终的 Pd/PiNe 多相催化剂具有小粒径 (4.5 nm) 和金属负载 (9.9 wt%)，可与大多数市售和常用的对应物相媲美。在这项贡献中，我们测试了 Pd/PiNe 系统在两个代表性交叉偶联 Heck 和 Hiyama 反应中的催化效率，并比较了与商业 Pd/C 催化剂获得的结果。生物质衍生溶剂 (GVL) 中的良好反应性证实了 Pd/PiNe 多相催化剂是一种有效的系统，可以在循环经济方法中整合到废物价值链中。此外，催化剂的效率也得到了扩展，以进行具有挑战性的连续 Hiyama-Heck 反应，以提供不同取代的（E )-1,2-二芳基乙烯。
• Synthesis of Esters by Functionalisation of CO2
  申请人：Commissariat a L'Energie Atomique et aux Energies Alternatives

  公开号：US20170240485A1

  公开（公告）日：2017-08-24

  The invention relates to a method for (I) producing a carboxylic ester of formula (I). Said method comprises the steps of: a) bringing an organosilane/borane of formula Si or B into contact with CO 2 , in the presence of a catalyst and an electrophilic compound of formula (III), the groups R 1 , R 2 , R 3 , R 4 , R 5 , Y, and M′ being as defined in claim 1; and optionally b) recovering the compound of formula (I) produced.

  该发明涉及一种制备化学式（I）的羧酸酯的方法。该方法包括以下步骤：a）在催化剂和化学式（III）的亲电性化合物的存在下，将化学式Si或B的有机硅烷/硼烷与CO2接触，其中所述的基团R1、R2、R3、R4、R5、Y和M'如权利要求1所定义；以及可选的b）回收所产生的化学式（I）的化合物。
• Rhodium(III)-Catalyzed Direct C–H Arylation of Various Acyclic Enamides with Arylsilanes
  作者：Xiaolan Li、Kai Sun、Wenjuan Shen、Yong Zhang、Ming-Zhu Lu、Xuzhong Luo、Haiqing Luo

  DOI：10.1021/acs.orglett.0c03578

  日期：2021.1.1

  The stereoselective β-C(sp2)–H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by

  通过Rh（III）催化的交叉偶联反应，说明了各种无环酰胺与芳基硅烷的立体选择性β-C（sp 2）-H芳基化反应。该方法的特点是非凡的功效和立体选择性，广泛的底物范围，良好的官能团耐受性以及采用环保的芳基硅烷。该方法的实用性由克级合成和产物的进一步精制证明。此外，Rh（III）催化的C–H活化被认为是反应机理中的关键步骤。
• Bench-Stable Cobalt Pre-Catalysts for Mild Hydrosilative Reduction of Tertiary Amides to Amines and Beyond
  作者：Alibek Nurseiit、Jaysan Janabel、Kristina A. Gudun、Aishabibi Kassymbek、Medet Segizbayev、Tulegen M. Seilkhanov、Andrey Y. Khalimon

  DOI：10.1002/cctc.201801605

  日期：2019.1.23

  unsaturated organic molecules, including the normally challenging reduction of amides to amines. With regard to hydrosilative reduction of amides even more effective and activator free catalytic systems can be generated from the bench‐stable, commercially available Co(acac)2 and Co(OAc)2 with dpephos and PPh3 ligands. These systems operate under mild conditions (<100 °C), with many examples of room temperature

  易于合成且稳定的二氯化钴配合物（dpephos）CoCl 2被用作预催化剂，用于向不饱和有机分子中添加多种硅烷，包括通常具有挑战性的酰胺还原为胺的方法。关于酰胺的氢化硅烷化还原，可以从具有dpephos和PPh 3配体的稳定的市售Co（acac）2和Co（OAc）2生成更有效和无活化剂的催化体系。这些系统在温和的条件下（<100°C）运行，其中有许多室温转变的例子，这是温和的钴催化酰胺氢化硅烷化反应的第一个例子。
• Pd-catalyzed cross-coupling reactions of arenediazonium salts with arylsilanes and aryltrifluoroborates in water
  作者：Kai Cheng、Baoli Zhao、Sai Hu、Xian-Man Zhang、Chenze Qi

  DOI：10.1016/j.tetlet.2013.09.001

  日期：2013.11

  Pd-catalyzed cross-coupling reactions of various arenediazonium salts with ArSi(OR)3 and KArBF3 have been achieved in good to excellent yields under simple aerobic conditions in water at room temperature. The functional group tolerance makes these transformations as attractive alternatives to the traditional cross-coupling approaches. Furthermore, the sequence can also be performed in a one-pot domino

  在简单的好氧条件下，在室温下于水中将各种芳族重氮鎓盐与ArSi（OR）3和KArBF 3进行Pd催化的交叉偶联反应，得到的产率高至优。官能团的耐受性使这些转化成为传统交叉偶联方法的诱人替代品。此外，该序列也可以在一锅多米诺骨牌过程中进行，省去了中间芳烃重氮盐的分离。

表征谱图