[1,3-二氢-1,3-双(2,4,6-三甲基苯基)-2H-咪唑-2-亚基](3-苯基-1H-茚-1-亚基)(三环己基膦)二氯化钌 | 254972-49-1

• 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 - 有机杂环化合物 - 唑类
• 中文名称: [1,3-二氢-1,3-双(2,4,6-三甲基苯基)-2H-咪唑-2-亚基](3-苯基-1H-茚-1-亚基)(三环己基膦)二氯化钌
• 中文别名: 三环己基膦[1,3-双（2,4,6-三甲基苯基）咪唑-2-亚烷基][3-苯基-1H-茚-1-基]二氯化钌（II）[catMETium®RF1]；三环己基磷并[1,3-双(2,4,6-三甲基苯基)咪唑-2-基][3-苯基-1H-茚-1-YLIDENE]二氯化钌；三环己基磷并[1,3-双(2,4,6-三甲基苯基)咪唑-2-基][3-苯基-1H吲哚-1-亚基]二氯化钌
• 英文名称: [dichloro(3-phenyl-1H-inden-1-yliden)(1,3-dimesityl-4,5-dihydro-imidazol-2-ylidene)(tricyclohexylphosphine)ruthenium(II)]
• 英文别名: RuCl₂(IMes)(PCy₃)(=C₉H₅Ph)；[(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)RuCl2(=C9H5Ph)(PCy3)]；Cl2Ru(PCy3)(IMes)(C9H5)Ph；Cl2Ru(PCy3)(N,N'-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)(C9H5)Ph；(1,3-bis(2,4,6-trimethylphenyl)-2,3-dihydro-1H-imidazol-2-ylidene)dichloro(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium；RuCl2(C9H5Ph)(tricyclohexylphosphine)(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)；RuCl2(PCy3)(ImMes)(3-phenylindenylidene)；RuCl2(C9H5Ph)(PCy3)(IMes)；1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-1-ium-2-ide;dichloro-(3-phenylinden-1-ylidene)ruthenium;tricyclohexylphosphane
• CAS: 254972-49-1
• 化学式: C₅₄H₆₇Cl₂N₂PRu
• 分子量: 947.089
• InChiKey: HBNBIWQQLMQFEU-UHFFFAOYSA-L

物化性质

• 稳定性/保质期：
  金属化合物。

计算性质

• 辛醇/水分配系数(LogP)：
  16.24
• 重原子数：
  60
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

SDS

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Section 1: Product Identification
Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene][3-phenyl-1H-inden-1-ylidene]rutheniu
Chemical Name:
m (II) dichloride, min. 95% [catMETium® RF1]
CAS Registry Number: 254972-49-1
Formula: RuCl2[C21H24N2][C15H10][P(C6H11)3]
EINECS Number: none
Chemical Family: organometallic complexes
Synonym: catMETium® IMesPCy

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 254972-49-1 100% 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: Ingestion, inhalation, skin, eyes
Eye Contact: Causes irritation to eyes
Skin Contact: Causes irritation to 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.

---

SECTION 5: Fire Fighting Measures
Flash Point: none
Autoignition Temperature: none
Explosion Limits: none
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 organic fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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

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SECTION 7: Handling and Storage
Handling and Storage: Store the material in a tightly sealed container 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: orange to brown powder
Molecular Weight: 947.07
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
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: none
Incompatibility: strong oxidizing agents
Decomposition Products: carbon dioxide, hydrogen chloride, carbon monoxide, organic fumes, phosphorus oxides, ruthenium oxide.

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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): 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 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：

  [1,3-二氢-1,3-双(2,4,6-三甲基苯基)-2H-咪唑-2-亚基](3-苯基-1H-茚-1-亚基)(三环己基膦)二氯化钌 在 乙烯 、 吡啶 作用下， 以 苯 为溶剂， 生成 methyltricyclohexylphosphonium chloride
  参考文献：
  名称：

  膦稳定复分解催化剂的一般分解途径：路易斯供体加速亚甲基提取

  摘要：

  对于范围广泛的 Grubbs 级复分解催化剂，空间上可接近的路易斯供体显示出在催化过程中加速分解。这些包括亚苄基衍生物 RuCl2(NHC)(PCy3)(=CHPh) (Ru-2: NHC = H2IMes, a; IMes, b; H2IPr, c; IPr, d; H2ITol, e) 和茚叉配合物 RuCl2(NHC)( PCy3)(=C15H10)（NHC = H2IMes，Ru-2f；IMes，Ru-2g）。所有这些预催化剂都形成亚甲基配合物 RuCl2(NHC)(=CH2) Ru-3 作为末端烯烃复分解中的活性物质，并生成 RuCl2(NHC)(PCy3)(=CH2) Ru-4 作为催化剂静止状态。在用 10 倍过量的吡啶处理后，Ru-4a 和 Ru-4b 在室温下的溶液中在几分钟内分解，通过三种配体（PCy3、亚甲基和一种氯化物）的净损失消除 [MePCy3]Cl A，以及甲

  DOI：

  10.1021/jacs.6b08372
• 作为产物：
  描述：

  双(三环己基磷)-3-苯基-1H-茚二氯化钌 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 在 lithium hexamethyldisilazane 作用下， 反应 0.75h， 以64%的产率得到[1,3-二氢-1,3-双(2,4,6-三甲基苯基)-2H-咪唑-2-亚基](3-苯基-1H-茚-1-亚基)(三环己基膦)二氯化钌
  参考文献：
  名称：

  根特勒接触：机械力支撑的现代钌烯烃复分解催化剂的合成

  摘要：

  描述了用于烯烃复分解的九种当代钌催化剂的机械化学合成，这是固态形成Ru卡宾有机金属配合物的第一个报道实例。在溶液中合成第二和第三代Ru催化剂时通常使用的三个关键有机金属转化-与原位形成的N-杂环卡宾（NHC）配体PCy 3进行膦配体（PCy 3）交换吡啶配体取代和亚苄基配体互换（已证明在机械化学条件下有效），提供了高纯度的靶标。机械化学方法不仅需要较少量的有机溶剂（对于合成而言是空的，仅对于纯化而言是可扩展的），而且还允许进行据报道在溶液相中不可能进行的转化。

  DOI：

  10.1002/cctc.201901444
• 作为试剂：
  描述：

  6-庚烯酸 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 [1,3-二氢-1,3-双(2,4,6-三甲基苯基)-2H-咪唑-2-亚基](3-苯基-1H-茚-1-亚基)(三环己基膦)二氯化钌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (2S,Z)-pyrrolo[1,2-c][1,4]azaoxacyclotetradec-8-ene-3,14-dione 、 (2S,E)-pyrrolo[1,2-c][1,4]azaoxacyclotetradec-8-ene-3,14-dione
  参考文献：
  名称：

  闭环复分解反应中的催化剂负载低

  摘要：

  描述了一种有效的闭环复分解反应程序。在几分钟内可以达到95％的二烯丙基丙二酸二乙酯在稀溶液中的转化率，达到TOF = 4173 min -1，而载有不饱和NHC配体的商业化Ru催化剂的负载量却非常低。通常，仅需50至250 ppm的催化剂即可将近定量转化为多种5-16元杂环化合物。此过程的实用性在5-8元的合成图示ñ -叔丁氧羰基（Ñ -Boc） -和ñ -对甲苯磺酰（Ñ-Ts）保护的环胺和9-16元内酯。大环脯氨酸基内酰胺的合成需要稍高的催化剂负载量。与单环产物一起，分离并表征了寡聚副产物，主要是环二聚体。

  DOI：

  10.1002/chem.201202207

文献信息

• Batchwise and Continuous Nanofiltration of POSS-Tagged Grubbs-Hoveyda-Type Olefin Metathesis Catalysts
  作者：Anna Kajetanowicz、Justyna Czaban、G. Rajesh Krishnan、Maura Malińska、Krzysztof Woźniak、Humera Siddique、Ludmila G. Peeva、Andrew G. Livingston、Karol Grela

  DOI：10.1002/cssc.201200466

  日期：2013.1

  New molecular‐weight‐enlarged metathesis catalysts, which bear polyhedral oligomeric silsesquioxane (POSS) tags, were synthesized and characterized. The catalysts can be recovered from the reaction mixture by using nanofiltration techniques and can be reused. It was found that the membranes Starmem 228 and PuraMem 280 successfully separate the catalyst from the post‐reaction mixtures to below 3 ppm

  合成并表征了带有多面体低聚倍半硅氧烷（POSS）标签的新型分子量增大的复分解催化剂。可以通过使用纳滤技术从反应混合物中回收催化剂，并可以重复使用。发现Starmem 228和PuraMem 280膜成功地将催化剂从反应后混合物中分离至3 ppm以下。还研究了这些带有POSS标签的催化剂在连续复分解反应中的应用。
• Process for Preparation of Ruthenium-Based Carbene Catalysts with Chelating Alkylidene Ligands
  申请人：Monsaert Stijn Frans

  公开号：US20130035494A1

  公开（公告）日：2013-02-07

  The invention relates to a method for preparation of ruthenium-based carbene catalysts with chelating alkylidene ligands (so-called “Hoveyda-type catalysts”) in a cross metathesis reaction by reacting a ruthenium-alkylidene complex with an olefin derivate in the presence of a polymer-supported cation-exchange resin (PSR) acting as a ligand (i.e. phosphine or amine) scavenger. Preferably, penta-coordinated ruthenium benzylidene or indenylidene carbene complexes are employed. The polymer-supported cation-exchange resin (PSR) may be an acidic resin (comprising sulfonic acid or carboxylic groups) or a resin containing carboxylic acid chloride (—COCl) groups or sulfonyl chloride (—SO 2 Cl) groups. The process is versatile and environmentally friendly; high yields are obtained.

  本发明涉及一种制备带有螯合烷基亚烯配体（称为“Hoveyda型催化剂”）的基于钌的卡宾催化剂的方法，通过在聚合物支持的阳离子交换树脂（PSR）的存在下，将钌-烷基亚烯配合物与烯烃衍生物反应，作为配体（即膦或胺）清除剂的交换树脂。优选地，采用五配位钌苄基亚烯或茚基亚烯卡宾配合物。聚合物支持的阳离子交换树脂（PSR）可以是酸性树脂（包含磺酸或羧基团）或含有羧酸氯（-COCl）基团或磺酰氯（-SO2Cl）基团的树脂。该过程具有多功能性和环保性，可获得高收率。
• Preparation of epothilone derivatives
  申请人：Puentener Kurt

  公开号：US20060241156A1

  公开（公告）日：2006-10-26

  The invention comprises a novel process for the preparation of an epothilone derivative of formula I: wherein R 1 and R 2 independently from each other represent hydrogen or protecting groups and R 3 is methyl or trifluoromethyl, which are useful precursors in the synthesis of the desoxyepothilone derivatives of the formula IV: wherein R 3 is methyl or trifluoromethyl. The desoxepothilones of formula IV inhibit the growth of tumor cells and are therefore promising candidates for novel anticancer agents.

  该发明涉及一种新型工艺，用于制备式I的环丙沙星衍生物，其中R1和R2各自独立地表示氢或保护基，R3为甲基或三氟甲基，这些衍生物在合成式IV的去氧环丙沙星衍生物的前体中有用，其中R3为甲基或三氟甲基。式IV的去氧环丙沙星具有抑制肿瘤细胞生长的作用，因此是新型抗癌药物的有前途的候选药物。
• Ruthenium–indenylidene complexes: powerful tools for metathesis transformations
  作者：Fabien Boeda、Hervé Clavier、Steven P. Nolan

  DOI：10.1039/b718287b

  日期：——

  Ruthenium-indenylidene complexes represent a class of robust and efficient pre-catalysts for olefin metathesis reactions. In this feature article, we provide an overview of the various complexes belonging to this family and summarise their use in various applications. The relation between the nature of ancillary ligands around the metal coordination sphere of these complexes and their catalytic activity

  钌-茚基络合物代表一类用于烯烃复分解反应的坚固而有效的预催化剂。在这篇专题文章中，我们概述了该家族的各种复合物，并总结了它们在各种应用中的用途。还讨论了这些配合物的金属配位域周围的辅助配体的性质与其催化活性之间的关系。
• Ruthenium Olefin Metathesis Catalysts Containing Six-Membered Sulfone and Sulfonamide Chelating Rings
  作者：Anna Szadkowska、Karolina Żukowska、Aleksandra E. Pazio、Krzysztof Woźniak、Renat Kadyrov、Karol Grela

  DOI：10.1021/om101129b

  日期：2011.3.14

  The preparation and X-ray structure characterization of new olefin metathesis initiators containing sulfone- and sulfonamide-substituted benzylidene ligands are described. We observed that these catalysts exhibit Ru center dot center dot center dot O(SO)R interactions, forming six-membered chelates. Tuning the electronic and steric factors of the benzylidene part as well as selecting the proper NHC ligands can have a direct impact on catalyst activity and stability, leading to promising new catalysts.