2-(二环己基膦)-1-(2,4,6-三甲基-苯基)-1H-咪唑 | 794527-14-3

• 物质功能分类: 化学试剂 - 有机试剂 - 膦配体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(二环己基膦)-1-(2,4,6-三甲基-苯基)-1H-咪唑
• 中文别名: 2-(二环己基膦)-1-异丙叉-1H-咪唑；1-(2,4,6-三甲基苯基)-2-(二环己基膦基)咪唑
• 英文名称: 2-(dicyclohexylphosphino)-1-mesityl-1H-imidazole
• 英文别名: 2-dicyclohexylphosphino-1-(2',4',6'-trimethylphenyl)imidazole；1-mesityl-2-(dicyclohexyl-phosphino)imidazole；1-mesityl-2-(dicyclohexylphosphino)imidazole；dicyclohexyl-[1-(2,4,6-trimethylphenyl)imidazol-2-yl]phosphane
• CAS: 794527-14-3
• 化学式: C₂₄H₃₅N₂P
• 分子量: 382.529
• InChiKey: ZRVANNJGPCSNAH-UHFFFAOYSA-N

物化性质

• 熔点：
  109°C
• 沸点：
  538.2±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 海关编码：
  29332900

SDS

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Section 1: Product Identification
Chemical Name: 1-(2,4,6-Trimethylphenyl)-2-(dicyclohexylphosphino)imidazole, min. 95% [cataCXium® PICy]
CAS Registry Number: 794527-14-3
Formula: C24H35N2P
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: cataCXium PlCy

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 794527-14-3 100% 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 mild irritation of the eyes.
Skin Contact: Causes mild irritation of the skin.
Inhalation: Inhalation of dust will lead to irritation of the respiratory tract.
Ingestion: No information available on the physiological effects of ingestion.
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 toxic organic fumes and phosphorus pentoxide.
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
Store in a tightly sealed container under an inert atmosphere of argon or nitrogen. Handle in an inert
Handling and Storage:
atmosphere. 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: 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 powder
Molecular Weight: 382.52
Melting Point: 109°
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 sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, phosphorus and 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 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：

  2-(二环己基膦)-1-(2,4,6-三甲基-苯基)-1H-咪唑 在 selenium 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  基于钌的烯烃加氢甲酰化催化剂的原位FTIR和NMR光谱研究

  摘要：

  通过咪唑取代的单膦修饰的均相钌配合物作为各种高效加氢甲酰化反应的催化剂，通过在反应条件下的原位红外光谱和NMR光谱进行了表征。由[Ru 3（CO）12]对于防止形成非活性的配体修饰的多核复合物起决定性作用。在催化过程中，检测到配体改性的单核钌（0）羰基化合物为静止状态。配体结构的变化对配体的配位行为并因此对催化性能具有至关重要的影响。配体中咪唑基部分的氮原子取代CO并不是一个普遍的特征，但是当满足配体的结构先决条件时就会发生。

  DOI：

  10.1002/chem.201504051
• 作为产物：
  描述：

  二环己基氯化膦 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 为溶剂， 反应 3.5h， 以50%的产率得到2-(二环己基膦)-1-(2,4,6-三甲基-苯基)-1H-咪唑
  参考文献：
  名称：

  [EN] NITROGEN-CONTAINING MONODENTATE PHOSPHINES AND THEIR USE IN CATALYSIS
  [FR] PHOSPHINES MONODENTELEES CONTENANT DE L'AZOTE ET LEUR UTILISATION DANS UNE CATALYSE

  摘要：

  公开号：

  WO2004101581A3
• 作为试剂：
  描述：

  邻溴三氟甲苯 、 在 四甲基乙二胺 、 仲丁基锂 、 zinc diacetate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-(二环己基膦)-1-(2,4,6-三甲基-苯基)-1H-咪唑 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 23.0h， 以4%的产率得到
  参考文献：
  名称：

  Pd 催化 γ,δ-不饱和 O-氨基甲酸酯通过不寻常的触变重排进行 γ-芳基化†

  摘要：

  当使用芳基亲电子试剂和膦配体的特定组合时，在γ,δ-不饱和O-氨基甲酸酯的芳基化中观察到不寻常的γ-选择性，涉及直接锂化、锌的金属转移和Negishi偶联。机理研究表明，其中涉及钯-二烯中间体的不寻常的立体特异性触合重排。

  DOI：

  10.1039/c8sc05058a

文献信息

• [EN] PROCESS FOR PREPARING CYCLIC CARBONATES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CARBONATES CYCLIQUES
  申请人：BASF SE

  公开号：WO2019034648A1

  公开（公告）日：2019-02-21

  The present invention relates to a process for preparing cyclic carbonates of formula Ia or Ib or mixtures thereof (Ia) (Ib) comprising the process step: a) reacting a propargylic alcohol of formula II (II) with carbon dioxide in the presence of at least one transition metal catalyst TMC1, which comprises a transition metal selected from metals of groups 10, 11 and 12 of the periodic table of the elements according to IUPAC and at least one bulky ligand.

  本发明涉及一种制备式Ia或Ib或它们的混合物（Ia）（Ib）的环状碳酸酯的方法，包括以下步骤：a）在至少一种过渡金属催化剂TMC1的存在下，将式II（II）的丙炔醇与二氧化碳反应，所述过渡金属选自IUPAC元素周期表第10、11和12族金属，并且至少含有一种庞大配体。
• METHOD FOR SELECTIVE PALLADIUM-CATALYZED TELOMERIZATION OF SUBSTITUTED DIENES
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：US20170275235A1

  公开（公告）日：2017-09-28

  A method for the selective synthesis of a tail-to-head, or a head-to-head, or a tail-to-tail telomer from an unsymmetrical diene by polymerizing the diene in the presence of [Pd(C 3 H 5 )COD]BF 4 and dicyclohexyl-[1-(2,4,6-trimethylphenyl)imidazol-2-yl]phosphane, Pd(OAc) 2 and triphenylphosphine, or [Pd(C 3 H 5 )COD]BF 4 and tris(2,4-di-tert-butylphenyl)phosphite in combination with a polar protic alcohol, an acidic polar protic alcohol, a polar aprotic ether, or a non-polar aprotic hydrocarbon is provided.

  提供了一种从非对称二烯通过在[Pd(C3H5)COD]BF4和二环己基-[1-(2,4,6-三甲基苯基)咪唑-2-基]膦烷，Pd(OAc)2和三苯基膦，或[Pd( )COD]BF4和三(2,4-二叔丁基苯基)磷酸酯的存在下，通过在极性质子醇，酸性极性质子醇，极性无水醚或非极性无水碳氢化合物中聚合二烯的方法，选择性地合成尾-头，头-头或尾-尾缩聚物。
• Dialkylphosphinoimidazoles as New Ligands for Palladium-Catalyzed Coupling Reactions of Aryl Chlorides
  作者：Surendra Harkal、Franck Rataboul、Alexander Zapf、Christa Fuhrmann、Thomas Riermeier、Axel Monsees、Matthias Beller

  DOI：10.1002/adsc.200404213

  日期：2004.12

  heterocycles by selective deprotonation and quenching with chlorophosphines. The novel ligands are easily tunable and show good to excellent performance in palladium-catalyzed Suzuki reactions and Buchwald–Hartwig aminations of aryl and heteroaryl chlorides.

  N-芳基-2-（二烷基膦基）咪唑和-苯并咪唑可通过选择性去质子化并用氯膦淬灭，方便地从相应的杂环中一步制备。这种新型的配体易于调节，并且在钯催化的Suzuki反应以及芳基和杂芳基氯化物的Buchwald-Hartwig胺化反应中表现出良好或优异的性能。
• Process for catalytically preparing aromatic or heteroaromatic nitriles
  申请人：Muller Nikolaus

  公开号：US20080194829A1

  公开（公告）日：2008-08-14

  A process is described for catalytically preparing optionally substituted aromatic or heteroaromatic nitrites of the general formula (I) Ar—CN   (I) by reacting the corresponding aryl halides of the general formula (II) Ar—X   (II) in which X is chlorine, bromine, iodine, triflate, nonaflate, mesylate or tosylate and Ar is an optionally substituted aromatic or heteroaromatic radical, characterized in that the reaction is performed in the presence of a palladium compound, a phosphine of the general formula (III) or (IV) where R is an alkyl radical and R′, R″ and R′″ are each an alkyl radical or an aryl radical or heteroaryl radical and A is an alkylene or arylene radical, and potassium hexacyanoferrate(II) or potassium hexacyanoferrate(III), optionally in a solvent and optionally with addition of a base.

  描述了一种催化制备通式（I）Ar—CN的芳香族或杂环芳香族硝酸酯的过程，其中通过将通式（II）Ar—X的相应芳基卤化物反应而得，其中X是氯、溴、碘、三氟甲磺酸酯、非甲磺酸酯、甲苯磺酸酯之一，Ar是一个可选择取代的芳香族或杂环芳香族基团，其特征在于在钯化合物、通式（III）或（IV）的膦存在下进行反应，其中R是烷基基团，R′、R″和R′″分别是烷基基团或芳基或杂芳基，A是烷基或芳基基团，以及六氰合铁酸钾(II)或六氰合铁酸钾(III)，可选地在溶剂中，并可选地加入碱。
• CATALYST AND PROCESS FOR THE CO-DIMERIZATION OF ETHYLENE AND PROPYLENE
  申请人：Eastman Chemical Company

  公开号：US20150080628A1

  公开（公告）日：2015-03-19

  Disclosed are novel catalyst solutions comprising an organic complex of nickel, an alkyl aluminum compound, a solvent, and a phosphine compound, that are useful for the preparation of butenes, pentenes and hexenes by the co-dimerization or cross-dimerization of ethylene and propylene. Also disclosed are processes for the dimerization of ethylene and propylene that utilize these catalyst solutions. The catalyst systems described herein demonstrate that, depending on the choice of phosphine compound used with the catalytically active nickel, it is indeed possible to lower the concentration of hexene olefins relative to butenes and pentenes, even in the presence of excess propylene. The selectivity to the linear or branched pentene product can also be controlled by the selection of the phosphine compound. The catalyst solutions may be used with mixtures of olefins.

  揭示了一种新型催化剂溶液，包括镍的有机络合物、烷基铝化合物、溶剂和膦化合物，用于通过乙烯和丙烯的共二聚或交叉二聚制备丁烯、戊烯和己烯。还揭示了利用这些催化剂溶液进行乙烯和丙烯二聚的工艺。本文描述的催化剂系统表明，根据与具有催化活性的镍一起使用的膦化合物的选择，确实可以降低相对于丁烯和戊烯的己烯烯烃浓度，即使存在过量的丙烯。通过选择膦化合物，还可以控制对线性或支链戊烯产物的选择性。催化剂溶液可与烯烃混合物一起使用。