1,3-双(4-氯苯基)咪唑氯化物 | 141556-46-9

• 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-双(4-氯苯基)咪唑氯化物
• 中文别名: 1,3-双(4-氯苯基)-1H-咪唑氯化物
• 英文名称: 1,3-bis(4'-chlorophenyl)imidazolium chloride
• 英文别名: 1,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chloride；1,3-bis(4-chlorophenyl)imidazol-1-ium;chloride
• CAS: 141556-46-9
• 化学式: C₁₅H₁₁Cl₂N₂*Cl
• 分子量: 325.625
• InChiKey: SANZEZUASUDVTC-UHFFFAOYSA-M

物化性质

• 熔点：
  251-252°C
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

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Section 1: Product Identification
Chemical Name: 1,3-Bis(4-chlorophenyl)imidazolium chloride, min. 97%
CAS Registry Number: 141556-46-9
Formula: [C15H11Cl2N2]Cl
EINECS Number: None
Chemical Family: organic amine
Synonym: 1,3-di-(4-chlorophenyl)imidazolium chloride

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 141556-46-9 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritiating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation, skin and eyes.
Eye Contact: Irritating to the eyes.
Skin Contact: Irritating to the skin.
Inhalation: Irritating to the nose, mucous membranes and 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 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: no data
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, foam or dry powder
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 fumes of nitrogen oxides and hydrogen chloride.
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 in a cool, dry place in a tightly sealed container.

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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: cream-colored powder
Molecular Weight: 325.62
Melting Point: 251-252°C
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: soluble

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SECTION 10: Stability and Reactivity
Stability: hygroscopic
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: exposure to moisture and strong bases.
Incompatibility: strong oxidizing agents, halogenated solvents and acidic solvents.
Decomposition Products: carbon dioxide, carbon monoxide, 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): 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-双(4-氯苯基)咪唑氯化物 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以43%的产率得到1,3-bis(4-chlorophenyl)imidazol-2-ylidene
  参考文献：
  名称：

  亲核卡宾的电子稳定

  摘要：

  已合成四种新的稳定亲核卡宾并对其进行结构表征。1,3,4,5-四甲基咪唑-2-亚基的分离证明了咪唑核在C-2位置稳定卡宾中心的显着能力。三个带有芳基取代基的咪唑-2-亚基的分离与基于先前报道的推测相反

  DOI：

  10.1021/ja00040a007
• 作为产物：
  描述：

  N,N'-bis(4-chlorophenyl)-ethane-1,2-diimine 、 氯甲基乙醚 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以66%的产率得到1,3-双(4-氯苯基)咪唑氯化物
  参考文献：
  名称：

  通过烷基自由基从N-杂环卡宾-硼烷络合物中提取氢的估计速率常数†

  摘要：

  已经通过吡啶-2-硫代氧羰基（PTOC）竞争动力学方法在单个浓度点上确定了壬基从20种N-杂环卡宾和硼烷（NHC-硼烷）的络合物中提取氢的速率常数。速率常数的范围是从<1×10 4到8×10 4 M -1 s -1。它们几乎不依赖于卡宾核的电子性质，但是存在随着卡宾N取代基尺寸的减小而增加速率常数的趋势。已经鉴定出两种有希望的具有小的N取代基的新试剂（R = Me）。

  DOI：

  10.1021/ol101014q
• 作为试剂：
  描述：

  聚合甲醛 在 1,3-双(4-氯苯基)咪唑氯化物 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以46.5%的产率得到羟乙醛
  参考文献：
  名称：

  Coupling of formaldehyde to glycoaldehyde using N-heterocyclic carbene catalysts

  摘要：

  甘醛（GA）是在N-杂环卡宾的存在下通过甲醛的自缩合反应制备的，生成甘醛和丙三醛（GlyAld），具有选择性形成甘醛。杂环卡宾通过向催化剂的盐形式中加入碱来原位生成。通过调节催化剂的活性位点，可以控制选择性，包括立体和/或电子调节。

  公开号：

  US07498469B1

文献信息

• Targeted and Systematic Approach to the Study of p<i>K</i>_a Values of Imidazolium Salts in Dimethyl Sulfoxide
  作者：Michelle H. Dunn、Nicholas Konstandaras、Marcus L. Cole、Jason B. Harper

  DOI：10.1021/acs.joc.7b00716

  日期：2017.7.21

  A range of more than 25 imidazolium salts, chosen for their differing steric and electronic features, were prepared, and their pKa values were determined using the bracketing indicator method. Through the systematic change in the structure of the imidazolium cation, the effect of varying substituents at each position on the heterocyclic ring was determined; particularly, the transmission of electronic

  制备了25种以上的咪唑鎓盐（根据其空间和电子特性的不同而选择），并使用包围指示剂方法确定了其p K a值。通过咪唑阳离子结构的系统变化，确定了杂环上每个位置的取代基的变化。特别是，使用Hammett参数对电子效果的传输进行了量化。这些新数据表明了去质子化所需的碱基强度以及将这些数据与相应碳烯的亲核性相关联的潜力。
• Novel organometallic compounds for use in electroluminescent devices
  申请人：Lin Chun

  公开号：US20050260448A1

  公开（公告）日：2005-11-24

  An organic light emitting device having an anode, a cathode and an organic layer between the anode and the cathode is provided. The organic layer comprises a carbene-metal complex having the structure: where R may be halo, hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and additionally or alternatively, two or more R groups on the same ring form independently a 5 or 6-member cyclic group, which may be cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and which may be substituted by one or more substituents J; and J may be R′, CN, CF 3 , C(O)OR′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, or SO 3 R′, and additionally or alternatively, two J groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group; each R′ may be halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl and heteroaryl.

  提供一种具有阳极、阴极和位于阳极和阴极之间的有机层的有机发光器件。该有机层包括具有以下结构的卡宾金属配合物： 其中，R可以是卤素、氢、烷基、烯基、炔基、芳基烷基、芳基、杂芳基、取代芳基、取代杂芳基或杂环基；并且另外或者替代地，同一环上的两个或更多R基团独立地形成一个5或6环成环基团，该环基团可以是环烷基、环杂烷基、芳基或杂芳基；并且可以被一个或多个取代基J取代；J可以是R′、CN、CF3、C（O）OR′、C（O）R′、C（O）NR′2、NR′2、NO2、OR′、SR′、SO2、SOR′或SO3R′，并且另外或者替代地，相邻环原子上的两个J基团形成一个融合的5或6环芳基团；每个R′可以是卤素、H、烷基、烯基、炔基、杂烷基、芳基烷基、芳基和杂芳基。
• Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes with <i>o</i>-, <i>m</i>-, and <i>p</i>-halogen-substituted aryl groups (X = F, Cl, Br, CF₃)
  作者：Roman O. Pankov、Darya O. Prima、Alexander Yu. Kostyukovich、Mikhail E. Minyaev、Valentine P. Ananikov

  DOI：10.1039/d2dt03665g

  日期：——

  the Pd–NHC bond but does not affect the Pd–NHC bond energy. Here, we report the first optimized synthetic approach to access a comprehensive range of o-, m-, and p-XC6H4-substituted NHC ligands, including incorporation into Pd complexes (X = F, Cl, Br, CF3). The catalytic activity of the obtained Pd/NHC complexes was compared in the Mizoroki–Heck reaction. For substitution with halogen atoms, the following

  通过开发优化的合成程序以获得咪唑盐和相应的金属配合物，制备了具有吸电子卤素基团的Pd/NHC 配合物（NHCs - N -杂环卡宾）。已经进行了结构 X 射线分析和计算研究，以评估卤素和 CF 3取代基对 Pd-NHC 键的影响，并提供了对分子结构可能的电子效应的深入了解。吸电子取代基的引入改变了 σ-/π- 对 Pd-NHC 键的贡献率，但不影响 Pd-NHC 键能。在这里，我们报告了第一个优化的合成方法，以获得全面的o -、m - 和p-XC 6 H 4 -取代的NHC配体，包括并入Pd络合物（X = F、Cl、Br、CF 3）。在 Mizoroki–Heck 反应中比较了所获得的 Pd/NHC 配合物的催化活性。对于用卤素原子取代，观察到以下相对趋势：X = Br > F > Cl，并且对于所有卤素原子，催化活性按以下顺序变化：m -X，p -X > o -X。相对催化活性的评估表明，与未取代的
• METHODS OF USING HOMOGENOUS RHODIUM CATALYSTS WITH N-HETEROCYCLIC CARBENE LIGANDS FOR THE HYDROFORMYLATION OF OLEFINS AND SUBSTITUTED OLEFINS
  申请人：Lyondell Chemical Technology, L.P.

  公开号：EP3191443A1

  公开（公告）日：2017-07-19
• Methods of Using Homogenous Rhodium Catalysts with N-Heterocyclic Carbene Ligands for the Hydroformylation of Olefins and Substituted Olefins
  申请人：Lyondell Chemical Technology, L. P.

  公开号：US20160068458A1

  公开（公告）日：2016-03-10

  A method of using homogenous rhodium catalysts comprising N-heterocyclic carbene ligands for the hydroformylation of olefins and substituted olefins is provided. In some aspects, the methods provided herein relate to the hydroformylation of allyl alcohol to 4-hydroxybutaldehyde in the presence of a rhodium catalyst which contains one or more N-heterocyclic carbene ligands of the formula: wherein R 1 , R 2 , R 3 , and R 4 are defined herein.