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Home > Encyclopedia > CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)

CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)

CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) structure

CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) 

structure
  • CAS No:

    578743-87-0

  • Formula:

    C27H36ClCuN2 *-

  • Chemical Name:

    CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)

  • Synonyms:

    CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I);Chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I),98%;[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I)chloride;Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I);[1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)copper;[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride;Chloro[1,3-bis(2,6-diisopropylphenyl)iMidazol-2-ylidene]copp;[(iPr)CuCl]

  • Categories:

    Organic Chemistry  >  Organometallic Compounds

CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) Basic Attributes

487.58714

486.186310

Characteristics

6.5

8.52990

white Powder

>300 °C

Safety Information

3

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) Use and Manufacturing

Methods of Manufacturing

Synthesis of [(IPr)CuCl]. This synthesis is as reported in the literature; see H. Kaur et al., Organometallics 2004, 23, 1157-1160. In a 250 mL Schlenk flask were added copper(I) chloride (1.0 g, 10.10 mmol), 1, 3-bis(2, 6-diisopropylphenyl)imidazolium chloride (IPr.HCl; 4.29 g, 10.10 mmol), and sodium tert-butoxide (0.97 g, 10.10 mmol). To this flask, dry tetrahydrofuran (100 mL) was added under an inert atmosphere of argon, and the mixture was magnetically stirred for 20 hours at room temperature. After the mixture was filtered through a plug of Celite and then evaporating the solvent under vacuum, a white solid was obtained (4.59 g, 9.40 mmol, 94percent). General procedure: To a stirred solution of imidazolium salts (0.045 mmol), NaOtBu (4.3 mg, 0.045 mmol) and CuCl (4.5mg, 0.045 mmol) was added THF (0.5 mL, 0.09 M) at 30 Add ligand L8850mg (2.0mmol), copper powder 128mg (2.0mmol) in 50mL flask, water 30 mL, 80 ~ 90 in an oil bath, the reaction was stirred for 30 hours, the reaction mixture was cooled to room temperature, filtered, the filter cake was washed 3 times with water, the filter cake dissolved in acetonitrile and filtered to remove unreacted copper powder, the solvent was evaporated under reduced pressure to give 390 mg of colorless crystals, a yield of 40percent.

Uses

Used for reduction of olefin and carbonyl group, carbene transfer reaction, olefin aziridine reaction and aldehyde methyleneation reaction.

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