1,3-二环己基苯并咪唑氯化物 | 1034449-15-4

• 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 - 苯并咪唑类
• 中文名称: 1,3-二环己基苯并咪唑氯化物
• 中文别名: 1,3-二环己基氯化苯并咪唑鎓；1,3 - 二环己基苯并咪唑氯化物
• 英文名称: 1,3-dicyclohexyl-1H-benzo[d]imidazol-3-ium chloride
• 英文别名: 1,3-di(cyclohexyl)benzimidazolium chloride；1,3-dicyclohexylbenzimidazolium chloride；1,3-dicyclohexylbenzimidazol-3-ium;chloride
• CAS: 1034449-15-4
• 化学式: C₁₉H₂₇N₂*Cl
• 分子量: 318.89
• InChiKey: JACUDTKAZHCIPU-UHFFFAOYSA-M

物化性质

• 熔点：
  216-220°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 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

SDS

---

Section 1: Product Identification
Chemical Name: 1,3-Dicyclohexylbenzimidazolium chloride, min. 97%
CAS Registry Number: 1034449-15-4
Formula: C19H27ClN2
EINECS Number: none
Chemical Family: organic amine hydrochloride
Synonym: none

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 1034449-15-4 100% no data no data

---

Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of 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

---

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: 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: No unusual fire or explosion hazards.

---

SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

---

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

---

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.

---

SECTION 9: Physical and Chemical Properties
Color and Form: white to off-white solid
Molecular Weight: 318.88
Melting Point: No data
Boiling Point: No data
Vapor Pressure: No data
Specific Gravity: no data
Odor: none
Solubility in Water: Insoluble

---

SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: No hazardous polymerization
Conditions to Avoid: prolonged exposure to air
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, nitrogen oxides, and organic fumes

---

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

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

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

---

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

---

SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not reportable under SARA 313.
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,3-二环己基苯并咪唑氯化物 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis and characterization of silver and gold NHC complexes: Crystal structures and mass spectral studies

  摘要：

  Mononuclear silver and gold complexes [Ag(BzlCy)(Cl)] (1) and [Au(BzlCy)(Cl)] (2) were synthesized starting from the N-heterocyclic carbene (NHC) BzlCy center dot HCl (1,3-Dicyclohexylbenzimidazolium chloride) and characterized by NMR and ESI-MS spectral studies. Molecular structures of complexes [Ag(Bzl-Cy)(Cl)] (1) and [Au(BzlCy)(Cl)] (2.THF) were determined by X-ray crystallography. Formation of different species of these complexes 1 and 2 in gas phase was investigated by electrospray ionization mass spectrometry in positive mode and compared with solution formulation. To better understand the nature of NHC complexes and their reactivity with phenyl acetylene in gas phase, we synthesized a negatively charge tag gold complex [Au((S)BzlCy)(Cl)] starting from (S)BzlCy.HCl which prepared by the sulphonation of BzlCy. We investigated the formation of intermediate species [Au((S)BzlCy)(PhC C)] by the coordination of phenyl acetylene to the charge-tag gold complex in gas phase. We compared the stability of these NHC complexes and also investigated the decomposed mixture by electrospray ionization. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.03.017
• 作为试剂：
  描述：

  1-bromo-2,3-dimethyl-2-butene 在 吡啶 、 nickel(II) iodide 、 bis(1,5-cyclooctadiene)nickel (0) 、 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine 、 1,3-二环己基苯并咪唑氯化物 、 四丁基溴化铵 、 potassium carbonate 、 magnesium chloride 、 sodium t-butanolate 、 锌 作用下， 以 2-甲基-2-丁醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 70.0h， 生成
  参考文献：
  名称：

  用于四元中心引入的酰胺衍生物的Mizoroki-Heck环化

  摘要：

  我们报告了酰胺衍生物的非脱羰基Mizoroki-Heck反应。该转化依赖于镍催化的使用，并使用空间受阻的三和四取代的烯烃进行，以得到含有季中心的产物。可以高收率获得所得的多环或螺环产物。而且，该方法的非对映选择性变体使得能够接近带有邻近的，高度取代的sp 3立体中心的加合物。这些结果表明，酰胺衍生物可以用作组装复杂支架的基础。

  DOI：

  10.1002/anie.201703174

文献信息

• Benzimidazol-2-ylidene ligated palladacyclic complexes of N,N-dimethylbenzylamine – Synthesis and application to C–C coupling reactions
  作者：Kerry-Ann Green、Paul T. Maragh、Kamaluddin Abdur-Rashid、Alan J. Lough、Tara P. Dasgupta

  DOI：10.1016/j.ica.2016.04.048

  日期：2016.8

  analysis and IR spectroscopy. Complex 2c was further characterized by X-ray diffraction studies. The catalytic activity of all three complexes was explored for the Suzuki–Miyaura and Heck–Mizoroki coupling reactions of simple aryl bromides.

  摘要由N，N-二甲基苄胺（dmba）和苯并咪唑-2-亚基配体衍生的五环配合物：1,3-二（环己基）苯并咪唑-2-亚基（BzImCy），1,3-二（叔丁基）苯并咪唑制备了-2-亚烷基（BzImtBu）和1，3-二（1-金刚烷基）苯并咪唑-2-亚烷基（BzImAd）。（BzImCy）Pd（Cl）dmba（2a）的产率为72％，但更具立体感的类似物：（BzImAd）Pd（Cl）dmba（2b）和（BzImtBu）Pd（Cl）dmba（2c）的产率为分别为34％和38％。获得为灰白色，湿气和空气稳定的结晶固体的复合物，并通过1 H NMR和13 C NMR光谱，CHN分析和IR光谱进行表征。配合物2c通过X射线衍射研究进一步表征。
• [EN] METHOD FOR COUPLING AN AROMATIC COMPOUND TO AN ALKYNE<br/>[FR] PROCÉDÉ DE COUPLAGE D'UN COMPOSÉ AROMATIQUE À UN ALCYNE
  申请人：DOW GLOBAL TECHNOLOGIES LLC

  公开号：WO2017030971A1

  公开（公告）日：2017-02-23

  In one aspect, there is provided a method of coupling an aromatic compound having a fluorosulfonate substituent to an alkyne. In another aspect, there is provided a method of coupling an aromatic compound having a hydroxyl substituent to an alkyne in a one-pot reaction.

  一方面，提供了一种将具有氟磺酸酯取代基的芳香化合物与炔烃偶联的方法。另一方面，提供了一种在一锅反应中将具有羟基取代基的芳香化合物与炔烃偶联的方法。
• Alternative Synthetic Methods for PEPPSI‐Type Palladium Complexes
  作者：Kerry‐Ann Green、Paul T. Maragh、Kamaluddin Abdur‐Rashid、Alan J. Lough、Tara P. Dasgupta

  DOI：10.1002/ejic.201402317

  日期：2014.8

  Alternative procedures are reported for the preparation of PEPPSI-type palladium complexes (PEPPSI = pyridine-enhanced precatalyst preparation stabilization and initiation) in good to excellent yields. One method involves the reaction of [(NHC)Pd(acac)Cl] complexes (NHC = N-heterocyclic carbene, acac = acetylacetonate) with hydrohalides (HX; X = Cl, Br, I) of pyridine or 2,6-lutidine. Two other one-pot

  报道了用于制备 PEPPSI 型钯配合物（PEPPSI = 吡啶增强的预催化剂制备稳定和引发）的替代程序，收率良好至极好。一种方法涉及 [(NHC)Pd(acac)Cl] 配合物（NHC = N-杂环卡宾，acac = 乙酰丙酮化物）与吡啶或 2,6-二甲基吡啶的氢卤化物（HX；X = Cl、Br、I）的反应. 另外两种一锅法合成涉及 Pd(acac)2、唑盐和吡啶氢卤化物（或 2,6-二甲基吡啶氢卤化物）。复合物以湿气和空气稳定的固体形式获得，并通过 1 H 和 13 C NMR 光谱、CHN 分析和红外光谱表征。讨论了各种合成程序和所需产品的产率。[1-(2,6-二异丙基苯基)-3-(2,4,
• [EN] METHOD FOR COUPLING A FLUOROSULFONATE COMPOUND WITH AN AMINE COMPOUND<br/>[FR] PROCÉDÉ DE COUPLAGE D'UN FLUOROSULFONATE AVEC UNE AMINE
  申请人：DOW GLOBAL TECHNOLOGIES LLC

  公开号：WO2016057770A1

  公开（公告）日：2016-04-14

  The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound.

  本公开说明描述了一种将第一化合物与第二化合物偶联的方法，该方法包括：提供具有氟磺酸酯取代基的第一化合物；提供包含胺基的第二化合物；在反应混合物中反应第一化合物和第二化合物，反应混合物包括至少一个第10族元素的催化剂，在有效偶联第一化合物和第二化合物的条件下进行反应。本公开说明还描述了一种一锅法将第一化合物与第二化合物偶联的方法。
• [EN] METHOD FOR COUPLING A FIRST AROMATIC COMPOUND TO A SECOND AROMATIC COMPOUND<br/>[FR] PROCÉDÉ DE COUPLAGE D'UN PREMIER COMPOSÉ AROMATIQUE À UN SECOND COMPOSÉ AROMATIQUE
  申请人：DOW GLOBAL TECHNOLOGIES LLC

  公开号：WO2015148931A1

  公开（公告）日：2015-10-01

  In one aspect, there is provided a method of coupling a first aromatic compound having a fluorosulfonate substituent to a second aromatic compound having a boron-containing substituent. In another aspect, there is provided a method of coupling a first aromatic compound having a hydroxyl substituent to a second aromatic compound having a boron-containing substituent in a one-pot reaction.

  在一个方面，提供了一种将具有氟磺酸酯取代基的第一芳香化合物与具有含硼取代基的第二芳香化合物偶联的方法。在另一个方面，提供了一种在一个锅反应中将具有羟基取代基的第一芳香化合物与具有含硼取代基的第二芳香化合物偶联的方法。