1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride Chemical Properties

Melting point:

278 °C (dec.)(lit.)

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

White, off-white or tan

Water Solubility 

Slightly soluble in water.

Sensitive 

Hygroscopic

InChIKey

AVJBQMXODCVJCJ-UHFFFAOYSA-M

CAS DataBase Reference

250285-32-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

No

HS Code 

29332900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride Usage And Synthesis

Chemical Properties

White to Light yellow to Light orange powder to crystal. soluble in methanol.

Uses

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).

Application

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; the methyl ester derivative of the drug Vadimezan. Moreover, it is an imidazolium salt that is active against all stages of Trypanosoma Cruzi and may represent a promising candidate for treatment of Chagas disease.

Definition

1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride, also known as IDip HCl or IPr HCl, is a common N-heterocyclic carbene precursors. It could used to produce a novel iron(III)-containing imidazolium salt [DIPrim][FeCl4] which is an effective and easy-to-use catalyst for the cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides bearing β -hydrogens[1-2].

Reactions

Precursor to Pd catalysts used in C-N and C-C coupling reactions.
Ligand used in double carbonylation reactions.
Precursor to Ni catalysts used in C-N coupling reactions.
Precursor to Cu catalysts used in copper hydride reactions.
Ligand used in Ru-catalyzed carbonylative C-H cyclization of 2-aryl phenols.

Safety

H300 (37.84%): Fatal if swallowed [Danger Acute toxicity, oral]
H315 (62.16%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (37.84%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (37.84%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H319 (62.16%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H400 (37.84%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (37.84%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

References

Suzuki-Miyaura Reaction
Esterification of α-Halo-α,β-unsaturated Aldehydes by Using a Carbene Catalyst
Cycloaddition of CO2 to Epoxides Catalyzed by N-Heterocyclic Carbene (NHC)–ZnBr2 System under Mild Conditions

[1] Yan C, et al. An efficient and recyclable iron(III)-containing imidazolium salt catalyst for cross-coupling of aryl Grignard reagents with alkyl halides. Science Bulletin, 2012; 57: 1953–1958.
[2] Hans M, et al. Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors. Beilstein Journal of Organic Chemistry, 2015; 11: 2318–2325.

1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride(250285-32-6)Related Product Information

• N,N'-Diethylthiourea
• 1,3-Diiodopropane
• 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98%
• 1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE
• 1,3-Propane sultone
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• 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
• 1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM TETRAFLUOROBORATE
• 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM TETRAFLUOROBORATE
• 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
• 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
• 1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold(I)chloride,95%
• 1,2-DIMETHYL-3-PROPYLIMIDAZOLIUM IODIDE
• 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE
• 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride
• 1,3-DIMETHYLIMIDAZOLIUM CHLORIDE