250285-32-6

Basic information

• Product Name: 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE
• Synonyms: 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,97%;1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,95%;A1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOLIUM CHLORIDE;1,3-Bis(2,6-diisopropylphenyl)-1H-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
• CAS NO: 250285-32-6
• Molecular Formula: C₂₇H₃₇N₂*Cl
• Molecular Weight: 425.05
• EINECS: 1592732-453-0
• Product Categories: organic amine;Achiral Nitrogen;NHC;Imidazolium Compounds;Ligands;N-Heterocyclic Carbene Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Chemical Synthesis;NHC Compounds
• Mol File: 250285-32-6.mol
• Article Data: 51

Chemical Properties

• Melting Point: 278 °C (dec.)(lit.)
• Appearance: White, off-white or tan/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Slightly soluble in water.
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE(250285-32-6)
• EPA Substance Registry System: 1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIUM CHLORIDE(250285-32-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 250285-32-6(Hazardous Substances Data)

Usage

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.

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.

References

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

InChI:InChI=1/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

Synthetic route

C34H50Cl2N4Pd (1207373-09-8) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With trifluoroacetic acid In chloroform-d1 at 20℃; for 12h; Inert atmosphere;	100%

formaldehyd (50-00-0) + 1,2-bis(2,6-diisopropylphenylimino)ethane (74663-75-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With chloro-trimethyl-silane In ethyl acetate at 70℃; for 2h;	97%
With chloro-trimethyl-silane In ethyl acetate at 70℃; for 2h; Inert atmosphere; Glovebox;	87%
With chloro-trimethyl-silane In ethyl acetate at 70℃; for 2.75h; Inert atmosphere;	86%

1,2-bis(2,6-diisopropylphenylimino)ethane (74663-75-5) + ethyl chloromethyl ether (3188-13-4) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Molecular sieve; Inert atmosphere;	94%
With air In tetrahydrofuran; water at 40℃; for 16h; Solvent;	65%
With water In tetrahydrofuran at 40℃; for 16h; Condensation;	47%

formaldehyd (50-00-0) + (1E,2E)-N1,N2-bis(2,6-diisopropylphenyl)-ethane-1,2-diimine (74663-75-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With chloro-trimethyl-silane In ethyl acetate at 70℃; for 2h;	90%
With chloro-trimethyl-silane In ethyl acetate at 70℃; for 2h;	89%
With hydrogenchloride In 1,4-dioxane; ethyl acetate at 20℃; for 17h;	86%
Stage #1: formaldehyd; (1E,2E)-N1,N2-bis(2,6-diisopropylphenyl)-ethane-1,2-diimine In toluene at 100℃; Formylation; Stage #2: With hydrogenchloride In 1,4-dioxane; toluene at 70℃; for 5h; chloridation;	47%
With hydrogenchloride In 1,4-dioxane; ethyl acetate at 20℃; Heating;	41%

formaldehyd (50-00-0) + Glyoxal (131543-46-9) + 2,6-diisopropylbenzenamine (24544-04-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With hydrogenchloride In methanol for 36h; Reflux;	84.6%

chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) (578743-87-0) → 1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-one (1060651-05-9) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With air In dimethylsulfoxide-d6 at 150℃; for 155h;	A 16% B 81%
With water; oxygen In dimethylsulfoxide-d6 at 150℃; for 155h; Kinetics; Sealed tube;	A 16 %Spectr. B 81 %Spectr.

methanol (67-56-1) + 1,2-bis(2,6-diisopropylphenylimino)ethane (74663-75-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
Stage #1: methanol; 1,2-bis(2,6-diisopropylphenylimino)ethane With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: With ammonium chloride In tetrahydrofuran	80%

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene (244187-81-3) → SiCl2*NHC + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With trichlorosilane In toluene at 25℃; for 12h; Inert atmosphere;	A 79% B n/a

1,2-bis(2,6-diisopropylphenylimino)ethane (74663-75-5) + paracetaldehyde (123-63-7) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With chloro-trimethyl-silane In ethyl acetate at 70℃; for 2.75h;	76%

formaldehyd (50-00-0) + 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 40℃; for 72h;	58%

{1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(pyridine)palladium + triethylamine (121-44-8) → {1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(N-ethylethanamine)palladium + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube;	A n/a B 54%

chloromethyl methyl ether (107-30-2) + 1,2-bis(2,6-diisopropylphenylimino)ethane (74663-75-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
at 40℃; for 16h; Sealed tube;	52%
at 40℃; for 16h; Sealed tube;	52%

2,6-diisopropylbenzenamine (24544-04-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 77.5 percent / formic acid / ethanol; H2O / 48 h 2.1: toluene / 100 °C 2.2: 47 percent / HCl / toluene; dioxane / 5 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / propan-1-ol; H2O / 1 h / 70 °C 2: 47 percent / water / tetrahydrofuran / 16 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: ethanol / 12 h / 20 °C 2: tetrahydrofuran / 18 h / 40 °C / Inert atmosphere View Scheme

Glyoxal (131543-46-9) + 2,6-diisopropylbenzenamine (24544-04-5) + ethyl chloromethyl ether (3188-13-4) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
Inert atmosphere;

trans-[PdCl2(1,3-diethylimidazole)(1,3-(2,6-(i-Pr)2C6H3)2C3H2N2)] → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
Stage #1: trans-[PdCl2(1,3-diethylimidazole)(1,3-(2,6-(i-Pr)2C6H3)2C3H2N2)] With silver tetrafluoroborate In [D3]acetonitrile at 80℃; for 48h; Inert atmosphere; Stage #2: With lithium chloride In [D3]acetonitrile Inert atmosphere;

C27H36Cl3N2P (1080030-15-4) + 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene (244187-81-3) → C54H72Cl2N4P(1+)*Cl(1-) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
at -30 - 20℃; for 50h; Inert atmosphere;

1,3-bis(2,6-diisopropylphenyl)imidazolium fluoride → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With chloroform

1-(2,6-diisopropylphenyl)-1H-imidazole (25364-47-0) + 2-chloro-1,3-bis(1-methylethyl)benzene → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
In acetonitrile for 36h; Reflux; Inert atmosphere; Schlenk technique;

Glyoxal (131543-46-9) + 2,6-diisopropylbenzenamine (24544-04-5) → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With chloro-trimethyl-silane In formic acid

{1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(N-ethylethanamine)palladium → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 21h; Inert atmosphere; Schlenk technique; Sealed tube;	21 %Chromat.

{1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(1-propylamine)palladium → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 21h; Inert atmosphere; Schlenk technique; Sealed tube;	18 %Chromat.

{1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(N,N-diethylethanamine)palladium → {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(N-ethylethanamine)palladium + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;	A 49 %Chromat. B 41 %Chromat.
In N,N-dimethyl-formamide at 140℃; for 21h; Inert atmosphere; Schlenk technique; Sealed tube;	A 32 %Chromat. B 56 %Chromat.
Multi-step reaction with 2 steps 1: chloroform-d1 / 24 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

{1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(N,N-diethylethanamine)palladium → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 2 steps 1: triethylamine / chloroform-d1 / 60 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 3 steps 1: chloroform-d1 / 24 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: 1,4-dioxane / 0.5 h / 50 °C / Inert atmosphere; Schlenk technique 3: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 3 steps 1: chloroform-d1 / 24 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: 1,4-dioxane / 0.5 h / 50 °C / Inert atmosphere; Schlenk technique 3: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 3 steps 1: chloroform-d1 / 24 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 3: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

{1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(pyridine)palladium → 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,4-dioxane / 0.5 h / 50 °C / Inert atmosphere; Schlenk technique 2: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 2 steps 1: 1,4-dioxane / 0.5 h / 50 °C / Inert atmosphere; Schlenk technique 2: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: N,N-dimethyl-formamide / 21 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

{1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(pyridine)palladium + triethylamine (121-44-8) → {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(N-ethylethanamine)palladium + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;	A 33 %Chromat. B 38 %Chromat.

1-bromomethyl-4-nitro-benzene (100-11-8) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis(2,6-diisopropylphenyl)-2-(4-nitrobenzylidene)-2,3-dihydro-1H-imidazole (1357448-32-8)

Conditions	Yield
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium tert-butylate In tetrahydrofuran at 20℃; for 8h; Inert atmosphere; Stage #2: 1-bromomethyl-4-nitro-benzene In tetrahydrofuran at 20℃; for 38h; Inert atmosphere;	100%
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium tert-butylate; sodium hydride In tetrahydrofuran at 25℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 1-bromomethyl-4-nitro-benzene In tetrahydrofuran at 48℃; for 72h; Schlenk technique; Inert atmosphere;	61%

bis(benzonitrile)palladium(II) dichloride (15617-18-2, 39958-10-6, 14220-64-5) + sodium cyclopentadienide + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → CpPd(IPr)Cl

Conditions	Yield
With KO(tBu) In tetrahydrofuran Ar; Pd compd.(2.5 mmol), ligand (2.5 mmol), and KO(tBu) (2.5 mmol) in THF, stirred at room temp. for 12 h, THF soln. of NaCp (5 mmol) added, mixt. stirred overnight at room temp.; chromd.;	99%

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis(2,6-diisopropylphenyl)-1H-imidazole-2(3H)-thione (1311297-12-7)

Conditions	Yield
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With sulfur In acetone at 40℃; for 0.25h; Stage #2: With triethylamine In acetone at 60℃;	99%
With potassium carbonate; sulfur In acetone at 60℃; for 16h; Reagent/catalyst;	99%
With potassium tert-butylate; sulfur In tetrahydrofuran at 20℃;	87%

2-Picolinic acid (98-98-6) + palladium dichloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → C33H40ClN3O2Pd

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	99%
With caesium carbonate In 1,4-dioxane at 80℃; for 20h; Schlenk technique; Inert atmosphere;	65%

bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [N,N'-bis-[2,6-(di-iso-propyl)phenyl]imidazol-2-ylidene·H][Pd(η3-cinnamyl)Cl2]

Conditions	Yield
In acetone at 60℃; for 1h;	99%
In neat (no solvent) for 0.0833333h; Solvent; Green chemistry;	99%
In acetone at 60℃; for 1h;	99%

bis(η3-allyl-μ-chloropalladium(II)) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [IPrH][Pd(η3-allyl)Cl2]

Conditions	Yield
In acetone at 60℃; for 1h;	99%
In acetone at 60℃; for 1h;	99%

(2-methylallyl)palladium-chloride dimer + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [N,N'-bis-[2,6-(di-iso-propyl)phenyl]imidazol-2-ylidene·H][Pd(η3-2-Me-allyl)Cl2]

Conditions	Yield
In neat (no solvent) for 0.0833333h; Green chemistry;	99%

bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [N,N'-bis-[2,6-(di-iso-propyl)phenyl]imidazol-2-ylidene·H][Pd(η3-crotyl)Cl2]

Conditions	Yield
In neat (no solvent) for 0.0833333h; Green chemistry;	99%

[Pd(η3-tBu-indenyl)(μ-Cl)]2 + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [N,N'-bis-[2,6-(di-iso-propyl)phenyl]imidazol-2-ylidene·H][Pd(η3-tBu-indenyl)Cl2]

Conditions	Yield
In neat (no solvent) for 0.0833333h; Green chemistry;	99%

7,8-benzoquinoline (230-27-3) + palladium dichloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → C40H44ClN3Pd

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;	99%

bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [IPr*·H][Pd(η3-crotyl)Cl2]

Conditions	Yield
for 0.0833333h;	99%

(2-methylallyl)palladium-chloride dimer + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [IPr*·H][Pd(η3-2-Me-allyl)Cl2]

Conditions	Yield
for 0.0833333h;	99%

bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium][Pd(η3-cin)Cl2]

Conditions	Yield
for 0.0833333h;	99%

copper dichloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium][CuCl3]

Conditions	Yield
Milling;	99%

palladium dichloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium][PdCl3]

Conditions	Yield
Milling;	99%

acetic acid (64-19-7) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis(2,6-diisopropylphenyl)imidazolium acetate

Conditions	Yield
With Amberlyst A26 hydroxide In methanol; water at 70℃;	98.9%

3-Chloropyridine (626-60-8) + palladium dichloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropiridyl)palladium(II) dichloride

Conditions	Yield
With sodium carbonate at 80℃; for 16h; Product distribution / selectivity;	98%
With caesium carbonate at 80℃; for 16h; Reactivity;	93%
With potassium carbonate at 80℃; for 16h; Product distribution / selectivity;	80%

chloroacetonitrile (107-14-2) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-imidazol-2-ylidene]acetonitrile (1225274-70-3)

Conditions	Yield
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium tert-butylate In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; Sonication; Stage #2: chloroacetonitrile In tetrahydrofuran at 20℃; for 72h; Inert atmosphere;	98%
With potassium tert-butylate In tetrahydrofuran-d8 at 20℃; anaerobic conditions; ultrasonification;

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis-(2,6-diisopropylphenyl)imidazolium hexafluorophosphate

Conditions	Yield
With ammonium hexafluorophosphate In water at 20℃; for 0.166667h; Inert atmosphere;	98%
With potassium hexafluorophosphate In water at 20℃; Inert atmosphere; Glovebox;

bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → ((1,3-bis(2,6-di-isopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloro)(3-phenylallyl)palladium (2)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 5h;	98%
With potassium carbonate In ethanol at 60℃; for 5h; Green chemistry;	98%
Stage #1: bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In acetone at 60℃; Stage #2: With triethylamine In acetone at 60℃;	77%

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → N,N'-1,3-bis(2,6-diisopropylphenyl)-2-iodoimidazolium chloride

Conditions	Yield
With N-iodo-succinimide In dichloromethane at 40℃; for 3h; Sealed tube;	98%

vinyl acetate (108-05-4) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 2-(1-acetoxy-1-ethyl)-1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (1134205-18-7)

Conditions	Yield
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium tert-butylate In tetrahydrofuran for 0.166667h; Stage #2: vinyl acetate In tetrahydrofuran	97%

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I)

Conditions	Yield
With dimethylsulfide gold(I) chloride; potassium carbonate In acetone at 60℃; for 1h; Reagent/catalyst; Solvent; Temperature; Time;	97%
Multi-step reaction with 2 steps 1: dichloromethane / 0.25 h 2: potassium carbonate / dichloromethane / 1.5 h View Scheme
Multi-step reaction with 2 steps 1: dimethyl sulfoxide; methanol / Schlenk technique; Inert atmosphere 2: dimethyl sulfoxide; methanol / 4 h / 20 °C / Schlenk technique; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: dichloromethane / Darkness 2: dichloromethane View Scheme
Multi-step reaction with 2 steps 1: acetone / 0.17 h / 60 °C 2: sodium acetate / acetone / 0.83 h / 60 °C View Scheme

copper(l) chloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium][CuCl2]

Conditions	Yield
Milling;	97%
In neat (no solvent, solid phase) for 0.166667h; Milling;

tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → bis(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)copper hexafluorophosphate

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran (Ar); glovebox; mixt. of Cu complex, ligand and NaO-t-Bu in THF was stirred for 6 h; filtered through Celite (THF); filtrate mixed with hexane; filtered; elem. anal.;	96%

lithium tetrakis(tetrahydrofuran)bis(3,3',5,5'-tetra-tert-butyl-2,2'-diphenolato)aluminate(III) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → (1,3-bis(2,6-diisopropylphenyl)imidazolinium)bis(3,3',5,5'-tetra-tert-butyl-2,2'-diphenolato)aluminate(III)

Conditions	Yield
In dichloromethane byproducts: LiCl; under inert gas, imidazolinium-compd. dissolved in CH2Cl2, aluminate-compd. in CH2Cl2 added whilst stirring; filtered through Celite, washed with CH2Cl2, solv. removed, elem. anal.;	96%

(tetrahydrothiophene)gold(I) chloride (39929-21-0) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium dichloroaurate(I) (1439915-35-1)

Conditions	Yield
In dichloromethane for 0.25h;	96%

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] (12354-84-6, 12354-85-7) + potassium carbonate (584-08-7) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → (η5-pentamethylcyclopentadienyl)(κ2-CO3)(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)iridium(III) hydrate

Conditions	Yield
In tetrahydrofuran; dichloromethane at 24 - 60℃; for 34h; Inert atmosphere;	96%

Upstream product

• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 3188-13-4 ethyl chloromethyl ether 
• 50-00-0 formaldehyd 
• 74663-75-5 (1E,2E)-N¹,N²-bis(2,6-diisopropylphenyl)-ethane-1,2-diimine 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 
• 1370557-21-3 1,3-bis(1,3,5-trimethylphenyl)-5,5-dimethyl-4-keto-tetrahydro-pyrimidinium chloride 
• 122-51-0 orthoformic acid triethyl ester 
• 121-44-8 triethylamine 
• 67-56-1 methanol 
• 131543-46-9 Glyoxal 
• 578743-87-0 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 
• 107-30-2 chloromethyl methyl ether 
• 25364-47-0 1-(2,6-diisopropylphenyl)-1H-imidazole 

Downstream Products

• 858345-70-7 (η5-cyclopentadienyl)(1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene)chloronickel(II) 
• 386742-84-3 bis[1,3-di(2',6'-diisopropylphenyl)imidazolin-2-ylidene]nickel⁽⁰⁾ 
• 578743-87-0 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 
• 1225274-68-9 1,3-bis-(2,6-diisopropylphenyl)-2-(2-oxiranylethylidene)-2,3-dihydro-1H-imidazole 
• 1225274-64-5 (E)-1,3-bis-(2,6-diisopropylphenyl)-2-(3-phenylprop-2-enylidene)-2,3-dihydro-1H-imidazole 
• 1225274-63-4 1,3-bis-(2,6-diisopropylphenyl)-2-(3-trimethylsilylprop-2-ynylidene)-2,3-dihydro-1H-imidazole 
• 1225274-70-3 [1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-imidazol-2-ylidene]acetonitrile 
• 1225274-61-2 1,3-bis-(2,6-diisopropylphenyl)-2-(4-methylbenzylidene)-2,3-dihydro-1H-imidazole 
• 1225274-67-8 2-cyclopropylmethylidene-1,3-bis-(2,6-diisopropylphenyl)-2,3-dihydro-1H-imidazole 
• 1225274-65-6 1,3-bis-(2,6-diisopropylphenyl)-2-(prop-2-enylidene)-2,3-dihydro-1H-imidazole 
• 1225274-62-3 1,3-bis-(2,6-diisopropylphenyl)-2-(3-methylbut-2-enylid-ene)-2,3-dihydro-1H-imidazole 
• 1225274-66-7 1-(1,3-bis-(2,6-diisopropylphenyl)imidazole-2-ylidene)-propanone 
• 1225274-69-0 ethyl 2-[1,3-bis-(2,6-diisopropylphenyl)-1,3-dihydro-imidazol-2-ylidenemethyl]acrylate 
• 1396781-09-1 C₂₇H₃₄⁽²⁾H₃N₂⁽¹⁺⁾*Cl^(1-) 

Relevant articles and documents

Biscarbene palladium(II) complexes. reactivity of saturated versus unsaturated N-heterocyclic carbenes

A series of designed palladium biscarbene complexes including saturated and unsaturated N-heterocyclic carbene (NHC) moieties have been prepared by the carbene transfer methods. All of these complexes have been characterized by 1H and 13C NMR spectroscopy as well as X-ray diffraction analysis. The reactivity of Pd-C(saturated NHC) is distinct from that of Pd-C(unsaturated NHC). The Pd-C(saturated NHC) bonds are fairly stable toward reagents such as CF3COOH, AgBF4 and I2, whereas Pd-C(unsaturated NHC) bonds are readily cleaved under the similar conditions. Notably, the catalytically activity of these palladium complexes on Suzuki-Miyaura coupling follows the order: (sat-NHC)2PdCl2 > (sat-NHC)(unsat-NHC)PdCl2 > (unsat-NHC)2PdCl2.

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Modular Ni(0)/Silane Catalytic System for the Isomerization of Alkenes

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