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656631

Sigma-Aldrich

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride

95%

Sinonimo/i:

1,3-Dimesitylimidazolidinium chloride, 4,5-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride, 4,5-Dihydro-1,3-dimesityl-1H-imidazolium chloride, N,N′-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride

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About This Item

Formula empirica (notazione di Hill):
C21H27ClN2
Numero CAS:
173035-10-4
Peso molecolare:
342.91
Numero MDL:
MFCD09039279
Codice UNSPSC:
12352005
ID PubChem:
24884213
NACRES:
NA.22

Saggio

95%

Impiego in reazioni chimiche

reagent type: ligand

Punto di fusione

280-286 °C

Stringa SMILE

[Cl-].Cc1cc(C)c(N2CC[N+](=C2)c3c(C)cc(C)cc3C)c(C)c1

InChI

1S/C21H27N2.ClH/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6;/h9-13H,7-8H2,1-6H3;1H/q+1;/p-1
COGMCBFILULEOS-UHFFFAOYSA-M

Categorie correlate

Descrizione generale

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride is an NHC (N-heterocyclic carbene) ligand which can bind with metal pre-catalysts to form complexes that show high catalytic activity.

Applicazioni

N-Heterocyclic Carbene Ligands

Precursor to an N-heterocyclic carbene catalysts used for:
  • A regioselective cycloadditon of terminal acetylenes with azides leading to 1,4-disubstitutedtriazoles. Internal acetylenes can also be used with this catalyst.
  • Markovnikov-type hydration of terminal alkynes
  • Hydrosilylation of ketones and cycloaddition of azides and alkynes
  • Suzuki-Miyaura reactions
  • Luminescence experiments

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

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
MKCK7041
MKCK0804
MKCH2819
MKCD4128
MKCB5038

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Vonika Ka-Man Au et al.
Journal of the American Chemical Society, 131(25), 9076-9085 (2009-06-03)
A new class of luminescent mononuclear and dinuclear N-heterocyclic carbene-containing gold(III) complexes has been synthesized and characterized. The X-ray crystal structures of most of the complexes have also been determined. Electrochemical studies reveal a ligand-centered reduction originated from the RC--N--CR
V Poza-Nogueiras et al.
Chemosphere, 199, 68-75 (2018-02-13)
Conventional water treatments are generally inadequate for degradation of emerging pollutants such as ionic liquids (ILs). The use of heterogeneous electro-Fenton (HEF) has attracted great interest, due to its ability to efficiently oxidize a wide range of organic pollutants operating
Silvia Díez-González et al.
Dalton transactions (Cambridge, England : 2003), 39(32), 7595-7606 (2010-07-14)
The preparation of three series of [(NHC)CuX] complexes (NHC = N-heterocyclic carbene, X = Cl, Br, or I) is reported. These syntheses are high yielding and only use readily available starting materials. The prepared complexes were spectroscopically and structurally characterized.
S. Roy and H. Plenio,
Advanced Synthesis & Catalysis, 352, 1014-1022 (2010)
Silvia Díez-González et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(29), 7558-7564 (2006-09-14)
A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high
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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.

N-Heterocyclic Carbene (NHC) Ligands

Emerging class of privileged ligands

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