三(三甲基硅)胺 | 1586-73-8

• 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: 三(三甲基硅)胺
• 中文别名: 九甲基三硅氮烷；九甲基三硅胺；三(三甲基硅基)胺；九甲基三硅氮烷,97%
• 英文名称: tris(trimethylsilyl)amine
• 英文别名: [[bis(trimethylsilyl)amino]-dimethylsilyl]methane
• CAS: 1586-73-8
• 化学式: C₉H₂₇NSi₃
• mdl: MFCD00047990
• 分子量: 233.577
• InChiKey: PEGHITPVRNZWSI-UHFFFAOYSA-N

物化性质

• 熔点：
  67-69 °C (lit.)
• 沸点：
  72 °C/10 mmHg (lit.)
• 密度：
  0.863
• 闪点：
  67°C
• 稳定性/保质期：
  常温常压下稳定，避免与强氧化剂和酸接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  13
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险品运输编号：
  UN 3259 8/PG 3
• 包装等级：
  III
• 危险类别：
  8
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

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Section 1: Product Identification
Chemical Name: Nonamethyltrisilazane, 98%
CAS Registry Number: 1586-73-8
Formula: N[Si(CH3)3]3
EINECS Number: 216-445-0
Chemical Family: organosilicon compound
Synonym: Tris(trimethylsilyl)amine

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 1586-73-8 100% no data no data

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Section 3: Hazards Identification
Irritating to skin, eyes and respiratory tract. Slowly generates ammonia gas in the presence of moisture.
Emergency Overview:
Symptoms are choking, wheezing, laryngitis, headache, nausea and vomiting.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes.
Eye Contact: Irritating to the eyes. May cause burns.
Skin Contact: Irritating to skin. May be harmful if absorbed through the skin.
Inhalation causes irritation of the respiratory tract. May cause edema and chemical pneumonitis. Inhalation
Inhalation:
may be fatal.
Ingestion: May cause nausea, vomiting and gastrointestinal tract burns, perforation and peritonitis, with abdominal pain.
Irritating to skin, eyes and respiratory tract. Ingestion may cause damage to the mouth, throat, esophagus and
Acute Health Affects:
gastrointestinal tract. Inhalation may be fatal due to edema and chemical pneumonitis.
Chronic Health Affects: No information available on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide or dry powder
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit toxic and corrosive fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Sweep up the solid and dispose of properly.

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SECTION 7: Handling and Storage
Handling and Storage: Store the material in a sealed container. Keep away from heat and moisture.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves. Consult with glove manufacturer to determine the proper type of glove.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white to colorless waxy solid
Molecular Weight: 233.6
Melting Point: 70-71°
Boiling Point: 76°C /12 mm
Vapor Pressure: no data
Specific Gravity: 0.8635
Odor: ammonia odor
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: contact with moisture
Incompatibility: acids, oxidizing agents and halogens
Decomposition Products: carbon dioxide, carbon monoxide, silicon dioxide, nitrogen oxides and organic fumes.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: No data available
Mutagenic Effects: No data available
Tetratogenic Effects: No data available

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to federal, state, and local regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  三(三甲基硅)胺 在 盐酸 作用下， 生成 氯化铵
  参考文献：
  名称：

  均相单核钴配合物将二氮高效催化转化为N（SiMe 3）3

  摘要：

  将三齿膦-烯胺基氨基正膦结合到钴（II）上产生四面体Co（NpNP iPr）Cl，1，在二氮中还原后生成T形顺磁性Co（I）络合物Co（NpNP iPr），2。这种顺磁性的T形衍生物与顺磁性的二氮衍生物Co（NpNP iPr）（N 2），3处于平衡状态，可以通过红外和低温紫外可见光谱法对其进行检测。既1和2充当分子氮转化均相催化剂为三（三甲基硅烷基）胺（N（森达3）3）（〜200当量，水解后定量为NH 4 Cl）在低温下存在过量KC 8和Me 3 SiCl的情况下。

  DOI：

  10.1021/acscatal.7b04351
• 作为产物：
  描述：

  甲基三氯硅烷 在 氯化氮 、 三(二甲胺基)膦 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.5h， 以40%的产率得到三(三甲基硅)胺
  参考文献：
  名称：

  Shaposhnikov, S. I.; Koidan, G. N.; Marchenko, A. P., Journal of general chemistry of the USSR, 1985, vol. 55, # 5, p. 963 - 966

  摘要：

  DOI：
• 作为试剂：
  描述：

  占吨酮 、 茴香烯 在 三(三甲基硅)胺 、 四甲基氟化铵 作用下， 反应 5.0h， 以98%的产率得到(E)-9-(3-(4-methoxyphenyl)allylidene)-9H-xanthene
  参考文献：
  名称：

  原位生成的催化酰胺基体系，可从烯丙基苯和羰基化合物形成1,3-二烯

  摘要：

  由氟化四甲基铵和N（TMS）3原位生成的酰胺基催化从烯丙基苯和羰基化合物的合成1,3-二烯。该系统适用于各种具有官能团（卤素，甲基，苯基，甲氧基，二甲基氨基，酯和酰胺部分）的烯丙基苯的转化。无环和环状二芳基酮，新戊苯酮，新戊醛和异丁酮苯用作偶联伙伴。还阐明了反式β-甲基对苯二酚在产物形成中的作用。

  DOI：

  10.1039/d0ob02007a

文献信息

• Preparation, Characterization, and Reactivity of Dinitrogen Molybdenum Complexes with Bis(diphenylphosphino)amine Derivative Ligands that Form a Unique 4-Membered P–N–P Chelate Ring
  作者：Takahiko Ogawa、Yuji Kajita、Yuko Wasada-Tsutsui、Hiroaki Wasada、Hideki Masuda

  DOI：10.1021/ic301577a

  日期：2013.1.7

  revealed that the competition between the back-donation from metal to dinitrogen and that from metal to ligand was affected by P–N–P bite angle and the dihedral angle of N-substituent of ligand. In order to examine the reactivity with respect to conversion of dinitrogen to ammonia, protonation and trimethylsilylation reactions of the coordinated dinitrogens were carried out for 2R.

  五个带有双（二苯基膦基）胺衍生物配体（L R）的二氮杂钼配合物，形成一个独特的4元PN螯合环，反-[Mo（N 2）2（L R）2 ]（2 R：R = PH，XY，p -MeOPh，3,5-我镨2 PH，我PR），共进行结合一氧化二分子的目的而制备。相应的两种二氯化物-钼络合物，反式-[MoCl 2（L R）2 ]（1 R：R ＝ Ph，Xy），也准备作为比较。测量了2 R的FT-IR光谱，并比较了ν（N≡N）值。此外，确定1 R（R = Ph，Xy）和2 R（R = Xy，3,5- i Pr 2）的X射线晶体结构Ph）被执行。这些实验结果表明配位的二氮分子容易受到二膦胺配体的N-取代基的影响。另外，为了研究二膦胺配体的性质对二氮钼配合物的影响，我们进行了DFT计算，重点是N取代基的差异，P–N–P平面与N取代基芳基之间的二面角，以及P–N–P咬合角度。该计算表明，金属向二氮的反向捐赠与金属
• Efficient Synthesis of 1,2,4-Dithiazolidine-3,5-diones [Dithiasuccinoyl-Amines] from Bis(chlorocarbonyl)disulfane Plus Bis(trimethylsilyl)amines
  作者：Michael J. Barany、Robert P. Hammer、R. B. Merrifield、George Barany

  DOI：10.1021/ja0455446

  日期：2005.1.1

  dithiasuccinoyl (Dts)-amine, serves as a readily removable amino protecting group for building blocks used in syntheses of peptides, glycopeptides, and PNA; it is also useful as a masked isocyanate and (inversely) as a sulfurization reagent for trivalent phosphorus. Bis(chlorocarbonyl)disulfane, the two-sulfur analogue of succinyl chloride, has been envisioned as a reagent for facile single-step elaboration of the

  1,2,4-二噻唑烷-3,5-二酮杂环，也称为二硫代琥珀酰 (Dts)-胺，作为一种易于去除的氨基保护基团，用于合成肽、糖肽和 PNA 的结构单元；它也可用作掩蔽异氰酸酯和（相反）用作三价磷的硫化试剂。双（氯羰基）二硫烷是琥珀酰氯的双硫类似物，已被设想为用于轻松单步制备杂环的试剂。然而，由于所讨论的原因，双（氯羰基）二硫烷直接与伯胺反应不能产生 Dts-胺。受到有机硅化学文献中的几个先例的启发，即三甲基甲硅烷基可以作为“大质子”，成功地，已开发出通过双（氯羰基）二硫烷与双（三甲基甲硅烷基）胺反应制备 Dts-胺的高产率方法。还介绍了旨在阐明这些观察结果的机械原因的研究。
• An isolable iron(<scp>ii</scp>) bis(supersilyl) complex as an effective catalyst for reduction reactions
  作者：Shogo Arata、Yusuke Sunada

  DOI：10.1039/c9dt00116f

  日期：——

  An isolable 14-electron iron bis(supersilyl) complex, Fe[Si(SiMe3)3]2(THF)2, was successfully synthesized from the reaction of FeBr2 with K[Si(SiMe3)3] and its structure was unambiguously determined by single-crystal X-ray diffraction analysis. The complex is coordinatively unsaturated and exhibits high catalytic activity toward the hydrosilylation of carbonyl compounds and the reductive silylation

  通过FeBr 2与K [Si（SiMe 3）3 ]的反应成功合成了可分离的14电子铁双（超甲硅烷基）配合物Fe [Si（SiMe 3）3 ] 2（THF）2。通过单晶X射线衍射分析确定。该络合物是配位不饱和的，并且表现出对羰基化合物的氢化硅烷化和二氮的还原甲硅烷基化的高催化活性。
• Syntheses and Some Reactions of Trimethylsilylated Dinitrogen Complexes of Tungsten and Molybdenum
  作者：Keiko Komori、Seiya Sugiura、Yasushi Mizobe、Masaki Yamada、Masanobu Hidai

  DOI：10.1246/bcsj.62.2953

  日期：1989.9

  hydrazido(2−) complexes such as [WI(NNH)(dpe)2] and [WI2(NNH2)(PMe2Ph)3] from [WI(NNSiMe3)(dpe)2] and mer-[WI2(NNHSiMe3)(PMe2Ph)3], respectively. When reduced with excess Na in THF under N2, complexes trans-[MI(NNSiMe3)(PMe2Ph)4] (M=Mo or W) and mer-[WI2(NNHSiMe3)(PMe2Ph)3] gave (Me3Si)2NH and NH3 in substantial yields, accompanied by the regeneration of the parent dinitrogen complexes. Additional amount

  一系列新的三甲基甲硅烷基二氮杂复合物 [MX(NNSiMe3)(L)4] (M=Mo: X=I; M=W: X=CF3SO3; L=PMe2Ph or 1/2 dpe; dpe=Ph2PCH2CH2PPh2) 和三甲基甲硅烷基肼 (2 −) 配合物 [MX2(NNHSiMe3)(PMe2Ph)3] (M=Mo: X=I 或 Br; M=W: X=CF3SO3) 和 [MX(NNHSiMe3)(dpe)2]X (M=Mo: X =I；M=W：X=CF3SO3) 是通过在苯中用 Me3SiX 处理二氮配合物顺式-[M(N2)2(PMe2Ph)4] 或反式-[M(N2)2(dpe)2] 制备的。通过与 MeOH 或 H2O 反应，末端氮原子上的三甲基甲硅烷基很容易被氢取代，得到例如二氮杂和肼基 (2-) 络合物，如 [WI(NNH)(dpe)2] 和 [WI2( NNH2)(PMe2Ph)3] 分别来自
• Indium Catalyzed Hydrofunctionalization of Styrene Derivatives Bearing a Hydroxy Group with Organosilicon Nucleophiles
  作者：Yuji Kita、Tetsuji Yata、Yoshihiro Nishimoto、Makoto Yasuda

  DOI：10.1021/acs.joc.7b02739

  日期：2018.1.19

  triiodide was the most effective catalyst, whereas typical Lewis acids such as TiCl4, AlCl3, and BF3·OEt2 were ineffective. Many functional groups were successfully introduced, and these resulted in yields of 31–86%. Various styrene derivatives were also applicable to this reaction. Mechanistic investigation revealed that the present hydrofunctionalization proceeded through Brønsted acid-catalyzed intramolecular

  加氢官能化是烯烃最重要的转化反应之一。在本文中，我们描述了使用各种类型的有机硅亲核试剂的三碘化铟催化带有羟基的烯烃的加氢官能​​化。三碘化铟是最有效的催化剂，而典型的路易斯酸（如TiCl 4，AlCl 3和BF 3 ·OEt 2）无效。成功引入了许多官能团，这些化合物的收率为31–86％。各种苯乙烯衍生物也适用于该反应。机理研究表明，目前的加氢官能​​化是通过布朗斯台德酸催化的烯烃分子内加氢烷氧基化反应进行的，然后是InI进行。环醚中间体的3-催化取代反应。

表征谱图