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1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride 1,3-双(2,4,6-三甲基苯基)氯化咪唑

规格: 98%
CAS: 141556-45-8
产品编号: H24188
MDL: MFCD02684541
品牌: INFI

氮杂环卡宾系列产品

氮杂环卡宾(NHC)被归类为有机实体,其特征是在氮杂环系统内的价壳中只有6个电子的二价碳原子(称为卡宾)。自从1991年Arduengo第一次分离得到稳定的游离氮杂环卡宾后,其作为一种高效的有机催化剂得到了迅速的发展,由于氮杂环卡宾的极性反转特性,使它在有机合成中构建复杂分子占有举足轻重的地位。氮杂环卡宾可以和过渡金属形成稳定的C-M键,与传统的配体相比,更加稳定且富电子,具有独特的立体效应和电子效应。传统的钯、铜等过渡金属络合物参与的反应必须在无氧条件下进行,而金属氮杂环卡宾催化剂由于具有较高的稳定性,甚至可以在有氧条件下进行一些交叉偶联反应。

杂环卡宾作为辅助配体具有以下优点:1)NHC复合物的强金属-卡宾键有利于紧密的结合动力学,从而提高中心金属的稳定性;2)比对应的膦催化剂具有更高的活性,有利于钯催化芳基氯化物的氧化加成率;3)与N原子键合的位阻基团的存在有助于从钯中对产物进行还原性消除;4)NHC配体的活性可通过远程引入电子导向取代基来进行修饰,也可通过取代基修饰获得手性、固定化和水溶解性。

研峰科技拥有完整配套的研发生产设备,通过前期大量的工艺研究、公司规范有效的管控流程及智能管理系统,实现了各类氮杂环卡宾产品稳定量产,质量稳定,满足客户要求,还可以根据客户的需要进行定制。详细产品情况请致电客服人员(400-106-2016)进行咨询。

Chemical Name1,3-Dimesityl-1H-imidazol-3-ium chloride
Synonym 1,3-Bis(mesityl)imidazolium chloride 1,3-Dihydro-1,3-dimesityl-2H-imidazol-2-ylidene monohydrochloride 1,3-Dimesitylimidazolium chloride 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride 1,3-双(2,4,6-三甲基苯基)氯化咪唑 1,3-二(2,4,6-三甲基苯基)氯化咪唑
PubChem Substance ID87559077
EC Number250-023-7
Beilstein Registry Number5468834
Reaxys-RN5468834
Chemical Name Translation1,3-双(2,4,6-三甲基苯基)氯化咪唑
MDL NumberMFCD02684541
CAS Number141556-45-8
GHS Symbol
WGK Germany3
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
    Hazard statements
    • H315 Causes skin irritation 会刺激皮肤
    • H319 Causes serious eye irritation 严重刺激眼睛
    • H335 May cause respiratory irritation 可能导致呼吸道刺激
      Signal word Warning
      Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
      Safety Statements
      • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
      • S36 Wear suitable protective clothing 穿戴适当的防护服;
      • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
      • S37 Wear suitable gloves 戴适当手套;
        Risk Statements
        • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
          Hazard Codes Xi
          Restrict -
        • {ALF} In the presence of a base such as KO-t-Bu, generates the imidazol-2-ylidene, an example of an N-heterocyclic carbene (NHC). NHCs are relatively strong bases, and valuable replacements for phosphine ligands in transition metal chemistry. They are relatively stable to dimerization, but sensitive to air and moisture, so are best generated in situ. Review: Angew. Chem. Int. Ed., 36, 2163 (1997). For a review of stable carbenes, see: Chem. Rev., 100, 39 (2000).
        • {ALF} See also 1,3-Bis(2,6-diisopropyl­phenyl)­imidazolium chloride, H27150.
        • {ALF} The carbene has also been reported to be an excellent nucleophilic catalyst in transesterification reactions, milder, more selective and more active than conventional systems: Org. Lett., 4, 3583, 3587 (2002).
        • {ALF} Used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction), see: J. Am. Chem. Soc., 121, 9889 (1999). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides, see: J. Org. Chem., 64, 3804 (1999); J. Organomet. Chem., 595, 186 (2000); Tetrahedron Lett., 45, 3511 (2004). Has been found to give superior results to phosphines in the coupling of sulfonyl chlorides with boronic acids: Org. Lett., 6, 95 (2004).
        • 141556-45-8 H24188 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
1,3-双(2,4,6-三甲基苯基)氯化咪唑

          化学属性

          Melting Point>300
          TSCANo
          Density1.422
          Mol. FormulaC21H25ClN2
          Appearance off-white to yellow pwdr.
          Mol. Weight341
          Danger-Level-
          pH-:-
          Redox-

          *以上化合物性质及应用等信息仅供参考