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| | 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride Basic information |
| Product Name: | 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride | | Synonyms: | 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,97%;1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLI&;1,3-BIS[2,6-BIS(1-METHYLETHYL)PHENYL]-1H-IMIDAZOLIUM CHLORIDE;1,3-Bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride;1,3-(2,6-Diisopropylphenyl)imidazolium Chloride;1,3-Bis(2,6-di-i-propylphenyl)imidazoliumchloride,min.95%;1,3-BIS(2,6-DI-I-PROPYLPHENYL) IMIDAZOLIUM CHLORIDE, MIN. 95%;1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,95% | | CAS: | 250285-32-6 | | MF: | C27H37ClN2 | | MW: | 425.05 | | EINECS: | 627-434-9 | | Product Categories: | organic amine;Achiral Nitrogen;NHC;Imidazolium Compounds;Ligands;N-Heterocyclic Carbene Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Chemical Synthesis;NHC Compounds | | Mol File: | 250285-32-6.mol |  |
| | 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride Chemical Properties |
| Melting point | 278 °C (dec.)(lit.) | | storage temp. | Inert atmosphere,Room Temperature | | form | Powder | | color | White, off-white or tan | | Water Solubility | Slightly soluble in water. | | Sensitive | Hygroscopic | | InChIKey | AVJBQMXODCVJCJ-UHFFFAOYSA-M | | CAS DataBase Reference | 250285-32-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | TSCA | No | | HS Code | 29332900 |
| | 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride Usage And Synthesis |
| Chemical Properties | White to Light yellow to Light orange powder to crystal. soluble in methanol. | | Uses | 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride is also used in organic synthesis, as well as a pharmaceutical intermediate. 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride is used as a reagent in the synthesis of NHC Copper(I) complexes bearing dipyridylamine ligands which exhibit interesting luminescent properties and are potential candidates for organic light-emitting diode applications. 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride is also used as a reagent in the synthesis of 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic Acid Methyl Ester (D476595); the methyl ester derivative of the drug Vadimezan (V084950). | | Definition | 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride, also known as IDip HCl or IPr HCl, is a common N-heterocyclic carbene precursors. It could used to produce a novel iron(III)-containing imidazolium salt [DIPrim][FeCl4] which is an effective and easy-to-use catalyst for the cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides bearing β -hydrogens[1-2].
| | Application | 1,3-Bis(2,6-Diisopropylphenyl)imidazolium chloride is also used as a reagent in the synthesis of 5,6-Dimethyl-9-Oxo-9H-xanthene-4-acetic acid methyl ester; the methyl ester derivative of the drug Vadimezan. Moreover, it is an imidazolium salt that is active against all stages of Trypanosoma Cruzi and may represent a promising candidate for treatment of Chagas disease. | | Reactions | Precursor to Pd catalysts used in C-N and C-C coupling reactions.
Ligand used in double carbonylation reactions.
Precursor to Ni catalysts used in C-N coupling reactions.
Precursor to Cu catalysts used in copper hydride reactions.
Ligand used in Ru-catalyzed carbonylative C-H cyclization of 2-aryl phenols.
 | | Safety | H300 (37.84%): Fatal if swallowed [Danger Acute toxicity, oral]
H315 (62.16%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (37.84%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (37.84%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H319 (62.16%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H400 (37.84%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (37.84%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] | | References | Suzuki-Miyaura Reaction
Esterification of α-Halo-α,β-unsaturated Aldehydes by Using a Carbene Catalyst
Cycloaddition of CO2 to Epoxides Catalyzed by N-Heterocyclic Carbene (NHC)–ZnBr2 System under Mild Conditions
[1] Yan C, et al. An efficient and recyclable iron(III)-containing imidazolium salt catalyst for cross-coupling of aryl Grignard reagents with alkyl halides. Science Bulletin, 2012; 57: 1953–1958.
[2] Hans M, et al. Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors. Beilstein Journal of Organic Chemistry, 2015; 11: 2318–2325. |
| | 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride Preparation Products And Raw materials |
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