2,6-双[1-(2,6-二异丙苯亚氨基)乙基]吡啶 | 204203-14-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,6-双[1-(2,6-二异丙苯亚氨基)乙基]吡啶
• 英文名称: N-(2,6-diisopropylphenyl)-N-((1E)-1-(6-[(1E)-N-(2,6-diisopropylphenyl)ethanimidoyl]pyridin-2-yl)ethylidene)amine
• 英文别名: 2,6-bis-[1-(2,6-diisopropylphenylimino)ethyl]pyridine；^iprPDI；2,6-Bis[1-(2,6-DI-I-propylphenylimino)ethyl]pyridine；N-[2,6-di(propan-2-yl)phenyl]-1-[6-[N-[2,6-di(propan-2-yl)phenyl]-C-methylcarbonimidoyl]pyridin-2-yl]ethanimine
• CAS: 204203-14-5
• 化学式: C₃₃H₄₃N₃
• 分子量: 481.725
• InChiKey: NVPUVWBDTWBFRF-UHFFFAOYSA-N

物化性质

• 沸点：
  573.6±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.424
• 拓扑面积：
  37.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36,S37,S39
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 2-8°C |

SDS

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Section 1: Product Identification
Chemical Name: 2,6-Bis[1-(2,6-di-i-propylphenylimino)ethyl]pyridine, 98%
CAS Registry Number: 204203-14-5
Formula: C33H43N3
EINECS Number: none
Chemical Family: organic amine
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 204203-14-5 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: No particular hazard associated with this material.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: May cause slight to mild irritation of the eyes
Skin Contact: May cause slight to mild irritation of the skin.
Inhalation: May be irritating to the nose, mucous membranes and respiratory tract.
No specific information is available on the physiological effects of ingestion. May cause vomiting and diarrhea.
Ingestion:
Acute Health Affects: May be irritating to skin, eyes and respiratory tract.
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: none
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
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 organic 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: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep away from heat and direct sunlight.

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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.
Ventilation: Material may form a fine dust. If possible, 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: Material may form a fine dust. If possible, 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: pale yellow powder
Molecular Weight: 481.69
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: slightly soluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture-stable solid
Hazardous Polymerization: none
Conditions to Avoid: none
Incompatibility: strong oxidizing agents
Decomposition Products: carbon dioxide, carbon monoxide, nitrogen oxides, and organic fumes.

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SECTION 11: Toxicological Information
RTECS Data: No specific information available on this product.
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 local, state and federal 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: not listed on the TSCA inventory
SARA (Title 313): not regulated by Title 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,6-双[1-(2,6-二异丙苯亚氨基)乙基]吡啶 在 氢气 、 tris(pentafluorophenyl)borane 作用下， 以 氘代甲苯 为溶剂， 120.0 ℃ 、405.33 kPa 条件下， 反应 24.0h， 以99%的产率得到N-[1-[6-[1-[2,6-di(propan-2-yl)anilino]ethyl]pyridin-2-yl]ethyl]-2,6-di(propan-2-yl)aniline
  参考文献：
  名称：

  沮丧的路易斯对对极性基材的无金属催化加氢

  摘要：

  在2006年，我们小组报告了第一个可逆地激活氢的无金属系统。该发现扩展到发现“加氢的路易斯化对”（FLP）催化剂。这就是本文的重点。综述了这种FLP加氢催化剂的开发和应用，并报道了一些以前未公开的数据。基板的范围扩大了。考虑了最佳条件和官能团耐受性，并将其应用于具有潜在商业意义的目标。还回顾了不对称FLP加氢的最新进展。考虑了FLP加氢催化剂的未来。

  DOI：

  10.1021/ic200663v
• 作为产物：
  描述：

  2,6-吡啶二羧酸二乙酯 在 对甲苯磺酸 sodium ethanolate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 40.0h， 生成 2,6-双[1-(2,6-二异丙苯亚氨基)乙基]吡啶
  参考文献：
  名称：

  [EN] HYDROSILYLATION CATALYSTS
  [FR] CATALYSEURS D'HYDROSILYLATION

  摘要：

  公开号：

  WO2011006044A3
• 作为试剂：
  描述：

  4-乙烯基-1-环己烯 、 二溴甲烷 在 2,6-双[1-(2,6-二异丙苯亚氨基)乙基]吡啶 、 cobalt(II) bromide 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以81%的产率得到4-Cyclopropylcyclohexene
  参考文献：
  名称：

  Regioselective Simmons–Smith-type cyclopropanations of polyalkenes enabled by transition metal catalysis

  摘要：

  一种钴催化剂在多烯的还原环丙烷化反应中赋予高度的位置选择性。

  DOI：

  10.1039/c7sc04861k

文献信息

• Tandem CH Activation/Arylation Catalyzed by Low-Valent Iron Complexes with Bisiminopyridine Ligands
  作者：Elise Salanouve、Ghania Bouzemame、Sébastien Blanchard、Etienne Derat、Marine Desage-El Murr、Louis Fensterbank

  DOI：10.1002/chem.201304459

  日期：2014.4.14

  Tandem CH activation/arylation between unactivated arenes and aryl halides catalyzed by iron complexes that bear redox‐active non‐innocent bisiminopyridine ligands is reported. Similar reactions catalyzed by first‐row transition metals have been shown to involve substrate‐based aryl radicals, whereas our catalytic system likely involves ligand‐centered radicals. Preliminary mechanistic investigations

  据报道，具有氧化还原活性的非纯双酰亚胺吡啶配体的铁配合物可催化未活化的芳烃和芳基卤化物之间的串联CH活化/芳基化反应。第一行过渡金属催化的类似反应已显示涉及基于底物的芳基，而我们的催化体系可能涉及以配体为中心的基团。基于光谱学和反应性研究的初步机理研究，结合DFT计算，我们建议反应可以通过内层CH活化途径进行，这在铁络合物中很少观察到。这种类似双电子的贵金属行为可以通过具有氧化还原活性的非纯双酰亚胺吡啶配体来维持。
• Chelate Bis(imino)pyridine Cobalt Complexes:  Synthesis, Reduction, and Evidence for the Generation of Ethene Polymerization Catalysts by Li⁺ Cation Activation
  作者：Nina Kleigrewe、Winfried Steffen、Tobias Blömker、Gerald Kehr、Roland Fröhlich、Birgit Wibbeling、Gerhard Erker、Julia-Christina Wasilke、Guang Wu、Guillermo C. Bazan

  DOI：10.1021/ja052129k

  日期：2005.10.1

  with Li[B(C6F5)4] in toluene followed by treatment with pyridine to yield [(ligMe)Co+-pyridine] (15). The reaction of the Co(II) complexes 10 or 12 with ca. 3 molar equiv of methyllithium gave the cobalt(I) complexes 16 and 17, respectively. Treatment of the (ligMe)CoCH3 (17) with Li[B(C6F5)4] gave a low activity ethene polymerization catalyst. Likewise, complex 16 produced polyethylene (activity = 33

  用FeCl 2 或CoCl 2 处理双(亚氨基苄基)吡啶螯合席夫碱配体8 (ligPh) 产生相应的(ligPh) MCl 2 配合物9 (Fe)和10 (Co)。10与甲基锂或“丁二烯-镁”的反应导致还原得到相应的(ligPh)Co(I)Cl产物11。类似地，双(芳基亚氨基乙基)吡啶配体(ligMe)与CoCl2反应得到(ligMe) )CoCl2 (12)。通过用“丁二烯-镁”处理来还原成(ligMe)CoCl (13)。配合物 13 在甲苯中与 Li[B(C6F5)4] 反应，然后用吡啶处理，得到 [(ligMe)Co+-吡啶] (15)。Co(II) 络合物 10 或 12 与约 3 摩尔当量的甲基锂分别得到钴 (I) 配合物 16 和 17。用Li[B(C6F5)4]处理(ligMe)CoCH3(17)得到低活性的乙烯聚合催化剂。同样，在用化学计量量的 Li[B(C6F5)4 处理后，复合物
• Novel olefin polymerization catalysts based on iron and cobalt
  作者：George J. P. Britovsek、Vernon C. Gibson、Stuart J. McTavish、Gregory A. Solan、Andrew J. P. White、David J. Williams、George J. P. Britovsek、Brian S. Kimberley、Peter J. Maddox

  DOI：10.1039/a801933i

  日期：——

  A new family of olefin polymerization catalysts, derived from iron and cobalt complexes bearing 2,6-bis(imino)pyridyl ligands, is described.

  一种基于含2,6-双(亚胺基)吡啶配体的铁和钴络合物的新型烯烃聚合催化剂系列被报道。
• Capturing Re(<scp>i</scp>) in an neutral N,N,N pincer Scaffold and resulting enhanced absorption of visible light
  作者：Philip Bulsink、Ahlam Al-Ghamdi、Prajesh Joshi、Ilia Korobkov、Tom Woo、Darrin Richeson

  DOI：10.1039/c6dt00661b

  日期：——

  (κ3-terpy)Re(CO)2X (X = Cl, Br). The synthesis, single crystal X-ray structural and spectroscopic characterization of these eight species documents their Re coordination geometries and demonstrates the accessibility of such compounds. The basic photophysical features of these compounds show significant elaboration in both number and intensity of the d–π* transitions observed in the UV-vis spectra relative to the

  largely （I）的有机金属和配位化学在很大程度上仅限于二齿α-二亚胺的连接和面部三羰基配位的几何形状。二齿二（亚氨基）吡啶和双齿三联吡啶络合物在氮气氛下的热转化在200-240℃下导致了家庭的Re（的我）钳形络合物[κ 3 -2,6- ARN CME} 2（NC 5 ħ 3）] Re（CO）2 X（Ar C 6 H 5，Me 2 C 6 H 3，i Pr 2 C 6 H3；X =氯，溴）和（κ 3 -terpy）的Re（CO） 2 X（X =氯，溴）。这八个物种的合成，单晶X射线结构和光谱表征证明了它们的Re配位几何形状，并证明了此类化合物的可及性。这些化合物的基本光物理特征表明，相对于二齿原料，在紫外可见光谱中观察到的d–π *跃迁的数量和强度都得到了很好的阐述，并使用了随时间变化的DFT计算对这些光谱进行了分析。
• Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives
  作者：Mahesh M. Parsutkar、Vinayak Vishnu Pagar、T. V. RajanBabu

  DOI：10.1021/jacs.9b07885

  日期：2019.9.25

  compounds from readily available precursors, using scalable and environmentally benign chemistry, can greatly impact their design, synthesis and eventually manufacture on scale. Functionalized cyclobutanes and cyclobutenes are important structural motifs seen in many bioactive natural products and pharmaceutically relevant small molecules. They are also useful precursors for other classes of organic compounds

  使用可扩展且环境友好的化学方法，发现用于从容易获得的前体制备手​​性化合物的对映选择性催化反应，可以极大地影响它们的设计、合成和最终的规模制造。功能化环丁烷和环丁烯是许多生物活性天然产物和药学相关小分子中的重要结构基序。它们也是其他类别有机化合物的有用前体，例如其他环烷烃衍生物、杂环化合物、立体定义的 1,3-二烯和催化不对称合成的配体。制造环丁烯的最简单方法是通过炔烃和烯基衍生物之间的对映选择性 [2+2]-环加成反应，这种反应历史悠久。然而，给出可接受的对映选择性的此类已知反应的范围非常窄，并且严格限于活化的炔烃和高反应性烯烃。在这里，我们公开了一种广泛适用的对映选择性 [2+2]-环加成反应，在各种炔烃和烯基衍生物（两种最丰富的有机前体类别）之间进行。关键的环加成反应使用衍生自易于合成的配体和地球上丰富的金属钴的催化剂。记录了 50 多种对映选择性在 86-97% ee 范围内的不同