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

Product Name: 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride
CAS No.: 250285-32-6
Chemical Name: 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride
Synonyms: IPr.HCl;1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1);1,3-bis(2,6-diisopropylphenyl)-1H-iMidazol-3-iuM chloride;1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOLIUM CHLORIDE;ium ChL;1,3-Bis(2,6-diisopropyL;VLOOKUP(C13,[1]Export!$D:$H,5,0);1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLI&;1,3-bis(2,6-diisopropylphenyl)-1H-iMidaz;1,3-Bis(2,6-diisopropylphenyl)-1H-iMidazoliu
CBNumber: CB3260739
Molecular Formula: C27H37ClN2
Formula Weight: 425.05
MOL File: 250285-32-6.mol

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

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)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
TSCA: No
HS Code: 29332900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 574074
Product name: 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride
Purity: 97%
Packaging: 500mg
Price: $68.7
Updated: 2025/07/31

Sigma-Aldrich

Product number: 574074
Product name: 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride
Purity: 97%
Packaging: 2g
Price: $177.8
Updated: 2025/07/31

TCI Chemical

Product number: R0316
Product name: 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride (HPMC encapsulated)
Packaging: 10EACH
Price: $60
Updated: 2025/07/31

TCI Chemical

Product number: D3611
Product name: 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride
Purity: >98.0%(HPLC)(T)
Packaging: 5g
Price: $403
Updated: 2025/07/31

TCI Chemical

Product number: D3611
Product name: 1,3-Bis(2,6-diisopropylphenyl)imidazolium Chloride
Purity: >98.0%(HPLC)(T)
Packaging: 25g
Price: $1400
Updated: 2025/07/31

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

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

50-00-0

74663-75-5

250285-32-6

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 Preparation Products And Raw materials

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View Lastest Price from 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE 250285-32-6
Price: US $0.10/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 1000 tons
Release date: 2020-04-24

Henan Fengda Chemical Co., Ltd

Product: 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride 250285-32-6
Price: US $200.00-1.00/KG
Min. Order: 1KG
Purity: 99%, 99.5% Sublimated
Supply Ability: g-kg-tons, free sample is available
Release date: 2023-12-30

henan kanbei chemical co.,ltd

Product: 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE 250285-32-6
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000kg
Release date: 2022-09-26

250285-32-6, 1,3-Bis (2,6-diisopropylphenyl) imidazolium chlorideRelated Search:

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 1,3-Diphenylacetone 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-2-(trichloromethyl)-imidazolidine Diethyl 1,3-acetonedicarboxylate 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

1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,97%

1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLI&

1,3-BIS[2,6-BIS(1-METHYLETHYL)PHENYL]-1H-IMIDAZOLIUM CHLORIDE

1,3-Bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride

1,3-(2,6-Diisopropylphenyl)imidazolium Chloride

1,3-Bis(2,6-di-i-propylphenyl)imidazoliumchloride,min.95%

1,3-BIS(2,6-DI-I-PROPYLPHENYL) IMIDAZOLIUM CHLORIDE, MIN. 95%

IPr.HCl

VLOOKUP(C13,[1]Export!$D:$H,5,0)

1,3-Bis(2,6-diisopropylphenyl)-1H-iMidazoliu

1,3-bis(2,6-diisopropylphenyl)-1H-iMidaz

1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,95%

A1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOLIUM CHLORIDE

1,3-Bis(2,6-di-i-propylphenyl)imidazolium chloride, 97+%

1,3-bis(2,6-diisopropylphenyl)-1H-iMidazol-3-iuM chloride

1,3-Bis(2,6-diisopropylphenyl)iMidazoliuM chloride, 97% 2GR

1,3-Bis[2,6-bis(isopropyl)phenyl]-1H-imidazol-3-ium chloride

1,3-Bis[2,6-bis(prop-2-yl)phenyl]-1H-imidazol-3-ium chloride

1,3-Bis(2,6-diisopropylphenyl)-1H-iMidazoliuM chloride

1,3-Bis(2,6-diisopropylphenyl)iMidazoliuM chloride 97%

1,3-bis[2,6-di(propan-2-yl)phenyl]iMidazol-1-iuM,chloride

2,5-Bis(2,6-diisopropylphenyl)imidazolium chloride

1,3-Bis(2,6-di-i-propylphenyl)imidazoliumchlorideipr HCl

1,3-Bis(2,6-diisopropylphenyl)imidazol-1-ium chloride

1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOLIUM CHLORIDE

1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE

1,3-Bis(2,6-diisopropyL

ium ChL

1,3-Bis[2,6-bis(isopropyl)phenyl]-1H-imidazol-3-ium chloride 97%

1,3-bis(2,6-diisopropylphenyl)imidazol-1-ium

1,3-Bis(2,6-diisopropylphenyl)imidazoliumChloride&gt

1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1)

1,3-bis[2,6-bis(1-methylethyl)phenyl]-1H-Imidazolium chloride (1:1)

1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride , IPr.HCl

250285-32-6

C27H37ClN2

C27H37N

C27H37N2Cl

C29H41N

Catalysis and Inorganic Chemistry

NHC Compounds

organic amine

Achiral Nitrogen

NHC

Imidazolium Compounds

Ligands

N-Heterocyclic Carbene Ligands

Synthetic Organic Chemistry

Catalysis and Inorganic Chemistry

Chemical Synthesis

NHC Compounds