1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Chemical Properties

Melting point:

280-286 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

Beige to pink-brown

Sensitive 

air sensitive

InChI

InChI=1S/C21H28N2.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;/h9-12H,7-8,13H2,1-6H3;1H

InChIKey

COGMCBFILULEOS-UHFFFAOYSA-M

SMILES

N1(CCN(C2=C(C)C=C(C)C=C2C)C1)C1C(C)=CC(C)=CC=1C.Cl

CAS DataBase Reference

173035-10-4

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

3

TSCA 

No

HS Code 

29332990

MSDS

• Language:English Provider:ACROS

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Usage And Synthesis

Chemical Properties

beige to pink-brown powder

Uses

N-Heterocyclic Carbene Ligands Precursor to an N-heterocyclic carbene catalysts

Uses

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

General Description

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.

reaction suitability

reagent type: ligand

Synthesis

Sodium borohydride (NaBH4, 4.24 g, 112.1 mmol) was slowly added to a solution of N,N'-bis(2,4,6-trimethylphenyl)ethylenediamine hydrochloride (8.0 g, 27.3 mmol) in tetrahydrofuran (THF, 100 mL) at 0 °C. Subsequently, concentrated hydrochloric acid (HCl, 4.5 mL, 2 eq.) was added dropwise over 30 min. After the dropwise addition, the reaction mixture was continued to be stirred at 0 °C for 20 min. Next, 3M hydrochloric acid (250 mL) was carefully added to the reaction flask at 0°C and the mixture was stirred for 1 hour, during which time the temperature was allowed to naturally rise to room temperature. Upon completion of the reaction, the white precipitate was collected by filtration and washed sequentially with water (200 mL) and 5% acetone-ether mixture (150 mL). The resulting product (9.4 g, 93% yield) was a white solid, which was dried under vacuum and prepared for use. The above obtained hydrochloride (8.5 g, 23 mmol) was suspended in triethyl orthoformate (HC(OEt)3, 35 mL, 162 mmol) and 2 drops of formic acid (HCO2H, ca. 1 mol%) was added as catalyst. The reaction mixture was heated to 120 °C and maintained for 5 hours under argon (Ar) protection. At the end of the reaction, it was cooled to room temperature and hexane (200 mL) was added to precipitate the product. After stirring for 1 hour, the white precipitate was collected by filtration, washed with hexane (200 mL) and dried under vacuum to give the final 1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride (IMesH2-HCl, 7.6 g, 96% yield).

References

[1] Synlett, 2006, # 3, p. 493 - 495
[2] Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2546 - 2558
[3] Patent: US9403854, 2016, B2. Location in patent: Page/Page column 41
[4] Tetrahedron, 1999, vol. 55, # 51, p. 14523 - 14534
[5] Organic Syntheses, 2010, vol. 87, p. 77 - 87

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE(173035-10-4)Related Product Information

• 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride
• 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
• 1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold(I)chloride,95%
• Ruthenium(III) chloride hydrate
• (1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE
• DICHLORO-[1,3-BIS(DIISOPROPYLPHENYL)IMIDAZOLYLIDENE]-(3-CHLOROPYRIDYL)PALLADIUM(II)
• (1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM
• GRUBBS CATALYST 2ND GENERATION
• 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
• 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II)dichloride
• Umicore M42
• Tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis(2,4,6-triMethylphenyl)-4,5-dihydroiMidazol-2-ylidene]rutheniuM(II)
• Umicore M41
• (1,3-BIS(2,4,6-TRIMETHYLPHENYL)-2-IMIDA&
• Isopentenylidene(1,3-dimesitylimidazolidin-2-ylidene) (tricyclohexylphosphine)ruthenium(II) dichloride
• RUTHENIUM, [1,3-BIS(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE]DICHLORO-[[2-ISOPROPOXY-5-(N-RESIN-LINKED AMINOSULFONYL)PHENYL]METHYLENE]
• TRICYCLOHEXYLPHOSPHINE[1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE][(PHENYLTHIO)METHYLENE]RUTHENIUM (II) DICHLORIDE
• [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)bis(3-bromopyridine)ruthenium(II)