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656623

Sigma-Aldrich

1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride

97%

Sinonimo/i:

N,N′-(2,6-Diisopropylphenyl)dihydroimidazolium chloride

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About This Item

Formula empirica (notazione di Hill):
C27H39ClN2
Numero CAS:
258278-25-0
Peso molecolare:
427.06
Numero MDL:
MFCD07369796
Codice UNSPSC:
12352005
ID PubChem:
24884212
NACRES:
NA.22

Saggio

97%

Stato

solid

Impiego in reazioni chimiche

reagent type: ligand

Punto di fusione

289-293 °C (lit.)

Stringa SMILE

[Cl-].CC(C)c1cccc(C(C)C)c1N2CC[N+](=C2)c3c(cccc3C(C)C)C(C)C

InChI

1S/C27H39N2.ClH/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;/h9-14,17-21H,15-16H2,1-8H3;1H/q+1;/p-1
LWPXTYZKAWSRIP-UHFFFAOYSA-M

Categorie correlate

Applicazioni

N-Heterocyclic Carbene Ligands
The palladium/1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (IPr·HCl) system can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.
Used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.
Used in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
MKCN0174
MKCH7463
MKCB3838
MKBV9204V
MKBP0376V

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Li Wang et al.
Organic letters, 11(4), 891-893 (2009-02-10)
Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by
Suzuki?Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols.
Arentsen K, et al.
Tetrahedron Letters, 45(17), 3511-3515 (2004)
Synlett, 366-366 (2006)
Palladium-(N-heterocyclic carbene) hydrogenation catalysts.
Jeroen W Sprengers et al.
Angewandte Chemie (International ed. in English), 44(13), 2026-2029 (2005-02-24)
Merritt B Andrus et al.
Organic letters, 4(12), 2079-2082 (2002-06-07)
[reaction: see text] Catalyst formed from N,N-bis(2,6-diisopropylphenyl)dihydroimidazolium chloride and palladium(II) acetate (2 mol %) was used, without added base, to efficiently produce Heck coupled products with olefins and aryl diazonium tetrafluoroborate substrates. The reactions were performed at room temperature, giving

Articoli

N-Heterocyclic Carbene Ligands

A wide range of NHC ligands are commonly available which exhibit high activities.

N-Heterocyclic Carbene (NHC) Ligands

Rapid progress in cross-coupling reactions of unactivated substrates catalyzed by metal complexes has transformed the chemical market-place through introduction of an extensive library of achiral and chiral phosphine ligands.

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