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

InChI

InChI=1S/C27H37N2.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;/h9-21H,1-8H3;1H/q+1;/p-1

InChIKey

AVJBQMXODCVJCJ-UHFFFAOYSA-M

SMILES

C1(N2C=C[N+](C3C(=CC=CC=3C(C)C)C(C)C)=C2)C(=CC=CC=1C(C)C)C(C)C.[Cl-]

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.

reaction suitability

reagent type: ligand

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]

Synthesis

1. Methanol (500 mL), 2,6-diisopropylaniline (63.8 mL, 340 mmol), glyoxal (40 wt% aqueous solution, 19 mL, 170 mmol), and formic acid (1 mL) were added to a 1000 mL round bottom flask. The reaction mixture was stirred at room temperature for 3 hours. 2. The reaction mixture was filtered and the yellow precipitate (3) was collected and washed with cold methanol. The precipitate was dried under vacuum overnight to give product (3) (70% yield, 44.2 g, 238 mmol). 3. The product (3) (200 g, 532 mmol) and ethyl acetate (2 L) were added to a 5 L round bottom flask and stirred until completely dissolved. Cool the solution to 0°C. 4. To a 500mL conical flask was added paraformaldehyde (20.7g, 690mmol) and a dioxane solution of 4N HCl (212mL, 851mmol), stirred for 10 minutes and then added to the above cooled solution. 5. The reaction mixture was stirred at room temperature for 2 hours and the precipitate was collected by filtration. 6. The precipitate was dissolved in methanol (200 mL), sodium bicarbonate (15.0 g) was added and stirred for 1 hour or until no bubbles were produced. 7. The solids were removed by filtration and the filtrate was reprecipitated by adding diethyl ether (250 mL) to the filtrate. 8. The product was collected by filtration, washed with ethyl ether and dried under vacuum to afford 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr-HCl, 4) as a white powder (70% yield, 158.25 g, 371 mmol). 9. The product was characterized by 1H NMR (CDCl3, 400 MHz) and 13C NMR (CDCl3, 400 MHz) and the data were consistent with the expected structure.

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
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• 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