[H27150] CAS 250285-32-6 | 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, 97%

CAS : 250285-32-6
MDL : MFCD02684545

Chemical Properties

Formula : C27H37ClN2
Formula weight : 425.05
Melting Point : ca 280° dec.
Sensitivity : Hygroscopic. Ambient temperatures.
Form : Powder
Solubility : Slightly soluble in water.

Literature References

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). 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). For Pd-catalyzed coupling of trimethoxysilanes with electron-deficient aryl chlorides, see: Org. Lett., 2, 2053 (2000). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-bis(2,6-diisopropylphenyl)imiazol-2-ylidene, enabling otherwise difficult coupling reactions of aryl chlorides with aryl and alkyl boronic acids, see: Synlett, 292 (2001) (includes alkylboronic acids: better yields than 1,3-dimesitylimidazol-2-ylidene); Org. Lett., 6, 4435 (2004); Tetrahedron Lett., 45, 3511 (2004). See also 1,3-Dimesityl­imidazolium chloride, H27535.

Applications

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 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 (D476595); the methyl ester derivative of the drug Vadimezan (V084950).

Grade Specifications

GHS Hazard and Precautionary Statements

Hazard Statements : H315-H319-H335Causes skin irritation.Causes serious eye irritation.May cause respiratory irritation.
Precautionary Statements : P261-P305+P351+P338-P302+P352-P321-P405-P501aAvoid breathing dust/fume/gas/mist/vapours/spray.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.IF ON SKIN: Wash with plenty of soap and water.Specific treatment (see label).Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.
위험 문구 : 36/37/38Irritating to eyes, respiratory system and skin.
안전 문구 : 26-37In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.