1,2-二甲基-1,1,2,2-四苯基乙硅烷 | 1172-76-5

• 物质功能分类: 化学试剂 - 硅烷试剂
• 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: 1,2-二甲基-1,1,2,2-四苯基乙硅烷
• 中文别名: 1,2-二甲基-1,1,2,2-四苯基二硅烷
• 英文名称: 1,2-dimethyl-1,1,2,2-tetraphenyldisilane
• 英文别名: 1,2-dimethyltetraphenyldisilane；tetraphenyldimethyldisilane；1,1,2,2-tetraphenyldimethyldisilane；methyl-[methyl(diphenyl)silyl]-diphenylsilane
• CAS: 1172-76-5
• 化学式: C₂₆H₂₆Si₂
• 分子量: 394.663
• InChiKey: JNZRJYXUMDPPRK-UHFFFAOYSA-N

物化性质

• 熔点：
  140-144 °C(lit.)
• 沸点：
  185°C/1mmHg(lit.)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲苯
• 最大波长(λmax)：
  239nm(Cyclohexane)(lit.)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	Tetraphenyldimethyldisilane Material Safety Data Sheet
Synonym:	None Known
CAS:	1172-76-5

Section 1 - Chemical Product MSDS Name:Tetraphenyldimethyldisilane Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1172-76-5	Tetraphenyldimethyldisilane	ca. 100	214-632-1

Hazard Symbols: XN
Risk Phrases: 20/21/22

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

---

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. Wash mouth out with 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:

---

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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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# 1172-76-5: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: colorless - after melting, dark brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 138-140 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Negligible.
Specific Gravity/Density:
Molecular Formula: C26H26Si2
Molecular Weight: 394.353

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1172-76-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tetraphenyldimethyldisilane - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 1172-76-5: No information available.
Canada
CAS# 1172-76-5 is listed on Canada's NDSL List.
CAS# 1172-76-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1172-76-5 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法：化学试剂、有机中间体、精细中间体、药物研发。

用途简介： 暂无内容

用途： 化学试剂、有机中间体、精细中间体、药物研发。

反应信息

• 作为反应物：
  描述：

  1,2-二甲基-1,1,2,2-四苯基乙硅烷 在 [Ni₂(1,3-diisopropyl-imidazolin-2-ylidene)₄(μ-1,5-cyclooctadiene)] 、 氢气 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、180.0 kPa 条件下， 反应 48.0h， 以83%的产率得到二苯甲基硅烷
  参考文献：
  名称：

  {{NHC）2 Ni 0 }处的Si–H键活化导致氢化硅烷基和双（甲硅烷基）配合物：催化Si–H / D交换，氢硅烷的无受体脱氢偶联以及乙硅烷加氢成氢硅烷的多功能工具† ‡

  摘要：

  镍（0）配合物[Ni 2（iPr 2 Im）4（COD）]（1）（iPr 2 Im = 1,3-二异丙基-咪唑啉-2-亚烷基）在化学计量和化学计量中对氢硅烷的独特反应性据报道催化反应。一系列的镍氢化硅烷基配合物顺式[[Ni（iPr 2 Im）2（H）（SiH n -1 R 4− n）]（n = 1，2）和镍双（硅烷基）配合物顺式-[Ni（ iPr 2 Im）2（SiH n -1 R 4− n）2 ]（n = 1、2、3）是通过1与氢硅烷H n SiR 4- n的化学计量反应合成的，并通过X射线衍射和光谱法进行了全面表征。这些氢化甲硅烷基络合物是阻碍完全氧化加成步骤的实例。由于剩余的Si–H相互作用，它们的Si–H距离非常短，并且在溶液中具有独特的动力学行为。顺式-[Ni（iPr 2 Im）2（H）（SiMePh 2）]（顺式-5）在室温下的溶液中显示NHC配体的动态位点交换，与C 6 D

  DOI：

  10.1039/c4dt01250j
• 作为产物：
  描述：

  二苯甲基硅烷 在 N-丁基-N-甲基哌啶溴盐 作用下， 以 乙腈 为溶剂， 以93 %的产率得到1,2-二甲基-1,1,2,2-四苯基乙硅烷
  参考文献：
  名称：

  氢硅烷电化学氧化脱氢生成硅自由基：利用可回收离子液体催化剂构建 Si-O/Si-Si 键的有效方法

  摘要：

  通过氢硅烷与 O-亲核试剂（例如苯酚、萘酚、醇和 H 2 O）的电化学氧化脱氢，开发了一种高效且可持续的 Si-O/Si-Si 键构建方法）或氢硅烷自缩合。该协议采用高导电性和可回收的离子液体作为催化剂，从而消除了对外部电解质和氢原子转移（HAT）剂的需要。该离子液体可以很容易地回收并重复使用至少八个周期，并且性能一致。值得注意的是，这种电化学方法表现出广泛的底物范围和高官能团兼容性（66 个示例，产率高达 96%）。初步机理研究表明，硅自由基是通过溴自由基和硅烷之间的氢原子转移过程产生的，KIE实验表明Si-H键断裂是反应的决定速率步骤。

  DOI：

  10.1039/d4gc02663b
• 作为试剂：
  描述：

  1-甲基-1-苯肼 在 1,2-二甲基-1,1,2,2-四苯基乙硅烷 、 potassium hydride 作用下， 生成 二苯甲基硅烷 、 1,4-dimethyl-1,4-diphenyl-2-tetrazine
  参考文献：
  名称：

  Chlorotrimethylsilane, hexamethyldisilane, and 1,2-dimethyl-1,1,2,2-tetraphenyldisilane as oxidizing agents in the conversion of hydrazines to 2-tetrazenes. Trimethylsilyl anion as a leaving group

  摘要：

  DOI：

  10.1021/jo00266a014

文献信息

• Pinacol couplings of a series of aldehydes and ketones with SmI2/Sm/Me3SiCl in DME
  作者：Aya Yoshimura、Tomokazu Saeki、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1016/j.tet.2015.06.007

  日期：2015.8

  The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system

  频哪醇耦合是最显著的方法来合成一个VIC -diols。在1,2-二甲氧基乙烷（DME）中存在三甲基氯硅烷（Me 3 SiCl）的情况下，二碘化mar（SmI 2）和金属metal的组合不仅成功诱导了芳族醛和酮的选择性频哪醇偶联，而且还诱导了脂肪族的选择性频哪醇偶联。对于使用SmI 2和Me 3 SiCl的还原系统，DME是最合适的溶剂。Me 3 SiCl是一种广泛使用的添加剂，可防止所形成的vic- diols分解，即内消旋-异构体，并控制其立体化学。特别地，空间受阻的脂族醛和酮的频哪醇偶联以优异的非对映选择性进行，以良好的产率提供dl-异构体。
• Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation
  作者：Laura Iannazzo、Gary A. Molander

  DOI：10.1002/ejoc.201200767

  日期：2012.9

  silylation of α,β-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poorly electrophilic acceptors such as phenylvinyl sulfone by cleavage of the Si-Si bond of a disilane reagent. The scope of this reaction was extended to various electrophiles bearing different electron-withdrawing groups and afforded the

  通过铜（I）催化的α，β-不饱和化合物的共轭硅烷化制备了几种烷基和乙烯基硅烷。首先研究了最佳反应条件，以通过乙硅烷试剂的 Si-Si 键断裂实现亲核硅物质与弱亲电子受体（如苯基乙烯基砜）的共轭加成。该反应的范围扩展到各种带有不同吸电子基团的亲电子试剂，并提供所需的取代烷基和乙烯基硅烷。在广泛的市售乙硅烷中，还研究了烷基-、芳基-和乙氧基乙硅烷的反应性。
• Electroreductive Synthesis of Polysilanes, Polygermanes, and Related Polymers with Magnesium Electrodes¹
  作者：Shigenori Kashimura、Manabu Ishifune、Natsuki Yamashita、Hang-Bom Bu、Masakatsu Takebayashi、Satsuki Kitajima、Daisuke Yoshiwara、Yasuki Kataoka、Ryoichi Nishida、Shin-ichi Kawasaki、Hiroaki Murase、Tatsuya Shono

  DOI：10.1021/jo990180z

  日期：1999.9.1

  poly(alkylarylsilane) (M(n) = 5200-31000, M(w)/M(n) = 1.4-1.8) in 5-79% yield. The effects of electrode material, monomer concentration, amount of supplied electricity, and ultrasound were investigated. This electroreductive method was also successfully applied to the synthesis of polygermanes, silane-geramane copolymers, and also poly[p-(disilanylene)phenylenes].

  在单个隔室中用Mg阴极和阳极对烷基芳基二氯硅烷进行电还原，得到5中的高分子量聚（烷基芳基硅烷）（M（n）= 5200-31000，M（w）/ M（n）= 1.4-1.8） -79％的产率。研究了电极材料，单体浓度，供电量和超声的影响。这种电还原方法也已成功地用于合成聚锗烷，硅烷-天竺葵共聚物以及聚[对-（二亚二甲苯基）亚苯基]。
• Direct construction of silicon–silicon bond by using the low-valent titanium reagent
  作者：Guoqiao Lai、Zhifang Li、Jiabang Huang、Jianxiong Jiang、Huayu Qiu、Yongjia Shen

  DOI：10.1016/j.jorganchem.2007.04.008

  日期：2007.7

  The reductive dimerization or polymerization of organochlorosilanes has been achieved by using the low-valent titanium reducing agent other than the alkali metals that are invariable used in the Wurtz-type coupling reaction. Applying this method, the corresponding disilanes or poly(methylvinylsilane) was obtained in good yields. The poly(methylvinylsilane) synthesized by this method is highly pure

  有机氯硅烷的还原二聚反应或聚合反应是通过使用除了在Wurtz型偶联反应中始终使用的碱金属以外的低价钛还原剂来实现的。应用该方法，以良好的产率获得了相应的乙硅烷或聚（甲基乙烯基硅烷）。通过这种方法合成的聚（甲基乙烯基硅烷）是高纯度的，具有高分子量和窄分子量分布（M w / M n  ＝ 1.6，M n  ＝ 16,860）。
• Reactions of Molybdenum Hydrides with Organochlorosilanes: Silicon–Silicon Bond Formation under Mild Conditions
  作者：Takahiro Asaeda、Joo Yeon Lee、Kyosuke Watanabe、Makoto Minato

  DOI：10.1246/cl.140203

  日期：2014.7.5

  Reactions of molybdenum hydrides containing polydentate phosphinoalkylsilyl ligands with a number of chlorosilanes have been investigated; this has led to the discovery of a novel type of a dechlorinative Si–Si coupling reaction.

  含有多齿膦烷基硅配体的钼氢化物与一系列氯硅烷的反应已得到研究；这导致发现了一种新颖的脱氯化硅硅偶联反应。

表征谱图