1,3-双(2,4,6-三甲基苯基)-2-咪唑烷亚基 | 173035-11-5

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 1,3-双(2,4,6-三甲基苯基)-2-咪唑烷亚基
• 中文别名: 1,3-双(2,4,6-三甲基苯基)-4,5-二氢咪唑-2-亚烷基；1,3-双(2,4,6-三甲基苯基)-4,5-二氢咪唑-2-亚基
• 英文名称: 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene
• 英文别名: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene；SIMes；1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene；1,3-dimesitylimidazolin-2-ylidene；1,3-dimesitylimidazolidin-2-ylidene；1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidin-2-ylidene；1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene；1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-2H-imidazol-1-ium-2-ide
• CAS: 173035-11-5
• 化学式: C₂₁H₂₆N₂
• 分子量: 306.451
• InChiKey: LSMWOQFDLBIYPM-UHFFFAOYSA-N

物化性质

• 熔点：
  85-100°C

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 储存条件：
  | 2-8°C |

SDS

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Section 1: Product Identification
Chemical Name: 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, min. 98%
CAS Registry Number: 173035-11-5
Formula: C21H26N2
EINECS Number: none
Chemical Family: N-heterocyclic carbene
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 173035-11-5 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Inhalation, skin, eyes
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes irritation to the skin
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information 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: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: Flammable solid.

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SECTION 6: Accidental Release Measures
Eliminate all ignition sources. Small spills can be mixed with vermiculite, sodium carbonate or other suitable
Spill and Leak Procedures:
non-combustible adsorbent and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep in a cool, dry place.

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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: 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 off-white powder
Molecular Weight: 306.45
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive, moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: exposure to air and moisture
Incompatibility: oxidizing agents
Decomposition Products: carbon monoxide, carbon 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
Mutagenic Effects: no data
Tetratogenic Effects: no data

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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): Flammable solids, Organic, N.O.S.
Hazard Class (CFR): 4.1
Additional Hazard Class (CFR): NA
Packaging Group (CFR): II
UN ID Number (CFR): UN# 1325
Shipping Name (IATA): Flammable solid, Organic, N.O.S.
Hazard Class (IATA): 4.1
Additional Hazard Class (IATA): NA
Packaging Group (IATA): II
UN ID Number (IATA): UN# 1325

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SECTION 15: Regulatory Information
TSCA: Not 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：

  1,3-双(2,4,6-三甲基苯基)-2-咪唑烷亚基 在 一氧化二氮 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 24.0h， 以62%的产率得到N-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]nitrous amide
  参考文献：
  名称：

  一氧化二氮和 N-杂环卡宾的加合物：合成、结构和反应性

  摘要：

  N-杂环卡宾 (NHC) 在环境条件下与一氧化二氮反应生成共价加合物。在晶体中，所有化合物都显示出弯曲的 N2O 基团，通过 N 原子连接到前一个卡宾碳原子。大多数加合物在室温下是稳定的，但加热会导致分解成相应的尿素。动力学实验表明 NHC-N2O 加合物的热稳定性取决于空间效应和电子效应。N2O 与 NHCs 的配位大大削弱了 NN 键，并且在与酸或乙酰氯的反应中观察到了容易的 NN 键断裂。另一方面，与四氟硼酸三苯甲基的反应导致末端 O 原子的共价修饰，并且在与亚硫酰氯的反应中观察到 C-N2O 键的断裂。IMes-N2O 的配位化学 (IMes = 1, 在与配合物 CuOTf、Fe(OTf)2、PhSnCl3、CuCl2 和 Zn(C6F5)2 的反应中探索了 3-dimesitylimidazol-2-ylidene)。结构分析表明，IMes-N2O 能够作为 N-供体、O-供体或螯合

  DOI：

  10.1021/ja4030287
• 作为产物：
  描述：

  1,3-双(2,4,6-三甲基苯基)-2-(三氯甲基)咪唑烷 以 氘代苯 为溶剂， 生成 1,3-双(2,4,6-三甲基苯基)-2-咪唑烷亚基
  参考文献：
  名称：

  热生成N杂环卡宾的通用方法。

  摘要：

  描述了通过二胺与适当取代的苯甲醛缩合来合成N-杂环卡宾（NHC）加合物的方法。这种简化的方法无需首先生成卡宾，然后对其进行保护即可提供NHC加合物。这些加合物进行热脱保护以原位生成N-杂环卡宾。通过使用热分析和光谱技术研究了加合物分解温度与催化剂结构的关系。重要的是，不同于衍生自氯仿的加合物，新的基于五氟苯的加合物更易于制备，并且在室温下稳定。这些加合物作为丙交酯的活性开环聚合（ROP），酯交换反应，

  DOI：

  10.1002/chem.200400196
• 作为试剂：
  描述：

  苯并恶唑 、 1,3-环庚二烯 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)-2-咪唑烷亚基 作用下， 以 neat (no solvent) 为溶剂， 以20%的产率得到2-cycloheptenylbenzo[d]oxazole
  参考文献：
  名称：

  镍通过杂芳烃的CH键活化促进环二烯的可切换氢杂芳基化

  摘要：

  我们通过杂芳烃的C–H键活化证明了Ni催化的环状二烯可切换氢杂芳基化反应。在N-杂环卡宾（NHC）配体的存在下，环二烯与吡咯的氢杂芳基化得到α-烯基-吡咯，无需使用任何外部氧化剂即可锻造Heck-like产物。相反，将配体改变为PCy 3将切换该反应歧管以提供另一种异构的β-烯基取代的唑。

  DOI：

  10.1016/j.tet.2015.03.066

文献信息

• [EN] CATALYST COMPLEXES WITH CARBENE LIGAND AND METHOD FOR MAKING SAME AND USE IN METATHESIS REACTION<br/>[FR] COMPLEXES DE CATALYSEURS AVEC UN LIGAND CARBÈNE, LEUR PROCÉDÉ DE FABRICATION ET LEUR UTILISATION DANS UNE RÉACTION DE MÉTATHÈSE
  申请人：GUANG MING INNOVATION COMPANY WUHAN

  公开号：WO2014108071A1

  公开（公告）日：2014-07-17

  This invention relates to catalyst compounds and the synthesis and applications useful in olefin metathesis reactions. The catalyst compounds of the invention are represented by the formula (I): wherein M is a Group 8 metal; X1 and X2 are anionic ligands; L1 and L2 are neutral two electron donor ligands. The present invention also relates to an easy applicable catalyst synthesis and the application in different olefin metathesis processes, e.g. Reaction Injection Molding (RIM), process to make α-olefins from fatty acid ester, e.g. methyl oleate.

  这项发明涉及催化剂化合物，以及在烯烃转化反应中有用的合成和应用。该发明的催化剂化合物由式(I)表示：其中M是8族金属；X1和X2是阴离子配体；L1和L2是中性的双电子给体配体。本发明还涉及一种易于应用的催化剂合成方法，以及在不同烯烃转化过程中的应用，例如反应注射成型（RIM）过程，用于从脂肪酸酯制备α-烯烃，例如甲基油酸甲酯。
• Single-Component Catalyst/Initiators for the Organocatalytic Ring-Opening Polymerization of Lactide
  作者：Szilárd Csihony、Darcy A. Culkin、Alan C. Sentman、Andrew P. Dove、Robert M. Waymouth、James L. Hedrick

  DOI：10.1021/ja050909n

  日期：2005.6.1

  readily release alcohol and the free carbene in solution. These alcohol adducts function as excellent single-component catalyst/initiators for the ring-opening polymerization of lactide under mild conditions, providing polymers with controlled molecular weights and narrow polydispersities. Multifunctional adducts were used to prepare poly(lactide)s of more complex architectures.

  描述了 1,3-dimesitylimidazolin-2-ylidene 的一系列伯醇和仲醇加合物的合成和表征。这些加合物在室温下是稳定的固体，但很容易在溶液中释放出醇和游离卡宾。这些醇加合物作为优异的单组分催化剂/引发剂用于丙交酯在温和条件下的开环聚合，提供具有可控分子量和窄多分散性的聚合物。多功能加合物用于制备更复杂结构的聚（丙交酯）。
• Modulating reactivity in iridium bis(N-heterocyclic carbene) complexes: influence of ring size on E–H bond activation chemistry
  作者：Nicholas Phillips、Christina Y. Tang、Rémi Tirfoin、Michael J. Kelly、Amber L. Thompson、Matthias J. Gutmann、Simon Aldridge

  DOI：10.1039/c4dt01398k

  日期：——

  and electronic properties of N-heterocyclic carbenes (NHCs) as a function of ring size have a profound effect on the reactivity of their late transition metal complexes. Comparison of closely related complexes featuring either a saturated 5- or 6-membered NHC, reveals that the larger ring is associated with an increased propensity towards intramolecular C–H activation, but with markedly lower reactivity

  N-杂环卡宾（NHCs）的空间和电子性质随环大小的变化对它们的后期过渡金属配合物的反应性具有深远的影响。比较具有5元或6元饱和NHC的密切相关的配合物，发现较大的环与分子内C–H活化的倾向增加相关，但与外部底物的反应性则明显较低。因此，[IrL 2（H）2 ] +类型的系统产生了相反的化学行为，主要反映了通过N键合的芳基取代基对金属中心进行二次稳定的不同可能性：高度不稳定的[Ir（5-Mes ）2（高）2 ] +只能通过捕集实验进行研究，而[Ir（6-Mes） 2（H） 2 ] +是空气和湿气稳定的，并且对许多外部试剂均无反应。使用适当的底物，可以利用这种增强的反应性，并且原位生成的[Ir（5-Mes） 2（H） 2 ] +能够进行分子间的BH和N-H活化化学反应。在H 3 B·NMe 2 H的情况下，这为通过单晶中子衍射方法研究胺/氨基硼烷配位提供了难得的机会。
• [EN] NOVEL TRANSITION METAL COMPLEXES, THEIR PREPARATION AND USE<br/>[FR] NOUVEAUX COMPLEXES DE MÉTAUX DE TRANSITION, LEUR PRÉPARATION ET UTILISATION
  申请人：LANXESS DEUTSCHLAND GMBH

  公开号：WO2014187973A1

  公开（公告）日：2014-11-27

  Novel transition metal complexes are provided which represent viable catalysts for a broad variety of reactions such as hydrogenation reactions and metathesis reactions. Novel preparation processes are made available via unprecedented routes inter alia not involving structures according to Grubbs I or Grubbs II catalysts.

  提供了新型过渡金属配合物，这些配合物可作为广泛反应的催化剂，如加氢反应和醇醚交换反应。通过前所未有的途径提供了新颖的制备方法，其中不涉及Grubbs I或Grubbs II催化剂的结构。
• Cyclopentadienyl–NHC Iron Complexes for Solvent‐Free Catalytic Hydrosilylation of Aldehydes and Ketones
  作者：David Bézier、Fan Jiang、Thierry Roisnel、Jean‐Baptiste Sortais、Christophe Darcel

  DOI：10.1002/ejic.201100762

  日期：2012.3

  Seven cyclopentadienyl-NHC piano-stool iron complexes were prepared and studied in the catalytic hydrosilylation of aldehydes and ketones under visible light irradiation. A significant acceleration of the rate was observed when the reactions were carried out under solvent-free conditions. Single-crystal X-ray structural analyses were performed for complexes 5 and 7.

  制备了七种环戊二烯基-NHC钢琴-凳铁配合物，并研究了可见光照射下醛和酮的催化氢化硅烷化反应。当反应在无溶剂条件下进行时，观察到速率显着加快。对配合物 5 和 7 进行了单晶 X 射线结构分析。