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250285-32-6 - 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, 97% - H27150 - Alfa Aesar

H27150 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, 97%

Codice CAS
250285-32-6
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
1g 148,00
5g 557,00
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1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, 97%

MDL
MFCD02684545

Proprietà chimiche

Formula
C27H37ClN2
Peso formula
425.05
Punto di fusione
ca 280° dec.
Sensibilità
Hygroscopic
Solubilità
Slightly soluble in water.

Applicazioni

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).

Note

Hygroscopic. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Stable under recommended storage conditions. Keep away strong oxidizing agents.

Letteratura

L Jafarpour.; ED Stevens.; SP Nolan. A sterically demanding nucleophilic carbene: 1, 3-bis (2, 6-diisopropylphenyl) imidazol-2-ylidene). Thermochemistry and catalytic application in olefin metathesis. Journal of Organometallic Chemistry. 2000606 (1), 49-54.

J Huang.; SP Nolan. Efficient cross-coupling of aryl chlorides with aryl Grignard reagents (Kumada reaction) mediated by a palladium/imidazolium chloride system. J. Am. Chem. Soc. 2000121 (42), 9889-9890.

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Codice tariffe armonizzato
2933.29
TSCA
No

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