582-60-5

Basic information

• Product Name: 5,6-Dimethylbenzimidazole
• Synonyms: 1H-Benzimidazole,5,6-dimethyl-(9CI);TIMTEC-BB SBB004105;5,6-dimethyl-1h-benzimidazol;dimedazol;dimesol;dimezol;dimethylbenzimidazole;5,6-DIMETHYLBENZIMIDAZOL
• CAS NO: 582-60-5
• Molecular Formula: C9H10N2
• Molecular Weight: 146.19
• EINECS: 209-488-1
• Product Categories: BENZIMIDAZOLE;Imidazol&Benzimidazole;Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 582-60-5.mol
• Article Data: 49

Chemical Properties

• Melting Point: 202-205 °C(lit.)
• Boiling Point: 255.81°C (rough estimate)
• Flash Point: 208.6 °C
• Appearance: Light beige/Powder
• Density: 1.0976 (rough estimate)
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: -20°C
• Solubility: Soluble in ethanol (50 mg/ml).
• PKA: 13.48±0.30(Predicted)
• Water Solubility: soluble
• Merck: 14,3236
• BRN: 116595
• CAS DataBase Reference: 5,6-Dimethylbenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dimethylbenzimidazole(582-60-5)
• EPA Substance Registry System: 5,6-Dimethylbenzimidazole(582-60-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DD8280000
• TSCA: Yes
• Hazardous Substances Data: 582-60-5(Hazardous Substances Data)

Usage

Chemical Properties

light beige powder

Definition

ChEBI: A dimethylbenzimidazole carrying methyl substituents at positions 5 and 6.

Purification Methods

Crystallise 5,6-dimethylbenzimidazole from diethyl ether. It sublimes at 140o/3mm. [Beilstein 23/6 V 454.]

InChI:InChI=1/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)

Synthetic route

4,5-dimethyl-1,2-phenylenediamine (3171-45-7) + orthoformic acid triethyl ester (122-51-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With gallium(III) triflate at 20℃; for 0.1h;	99%
With aminosulfonic acid In methanol at 20℃; for 1h;	94%
iodine In acetonitrile at 20℃; for 0.666667h;	93%

methanol (67-56-1) + 4,5-dimethyl-2-nitrobenzenamine (6972-71-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With iron; ammonium chloride at 68 - 70℃; for 48h; Inert atmosphere;	99%

N-formylbenzamide (4252-31-7) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With pyridinium p-toluenesulfonate In tetrahydrofuran at 50℃; for 9h; Inert atmosphere; Green chemistry;	96%

formic acid (64-18-6) + 4,5-dimethyl-1,2-dinitrobenzene (610-23-1) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 6h; Inert atmosphere; chemoselective reaction;	95%

4,5-dimethyl-2-nitrobenzenamine (6972-71-0) + orthoformic acid triethyl ester (122-51-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	94%
With iron; ytterbium(III) triflate at 75℃; for 3h;	82%

formic acid (64-18-6) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With tetrabutyl-ammonium chloride In water; toluene at 160℃; for 0.166667h; Microwave irradiation;	93%
With chloro-trimethyl-silane In water; N,N-dimethyl-formamide at 120℃; for 0.166667h; Microwave irradiation;	93%
In methanol at 20℃; under 1551.49 Torr; Flow reactor; Inert atmosphere;	38%

carbon dioxide (124-38-9) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With bis[1,2-bis(diphenylphosphine)ethane]ruthenium dichloride; hydrogen at 120℃; under 112511 Torr; for 40h; Green chemistry;	93%
With dimethylamine borane In ethanol; water at 100℃; under 750.075 Torr; for 24h;	93%
With tris(pentafluorophenyl)borate; phenylsilane In tetrahydrofuran at 120℃; under 7500.75 Torr; for 24h; Autoclave;	62%

4,5-dimethyl-1,2-phenylenediamine (3171-45-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With Imidazole hydrochloride at 120℃; for 6h;	93%
With phenylsilane at 120℃; for 12h;	50%
With Triethoxysilane; carbon dioxide; tris(pentafluorophenyl)borate at 120℃; for 24h;	99 %Spectr.

1-benzyl-5,6-dimethyl-1H-benzo[d]imidazole (15776-99-5) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	92%

oxalic acid (144-62-7) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
In 1,4-dioxane at 120℃; for 6h; Green chemistry;	92%

formic acid (64-18-6) + 4,5-dimethyl-2-nitrobenzenamine (6972-71-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With palladium 10% on activated carbon; triethylamine at 150℃; for 0.0833333h; Microwave irradiation;	91%

methanol (67-56-1) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 130℃; for 48h; Autoclave;	90%

formic acid (64-18-6) + N-(2-amino-4,5-dimethylphenyl)formamide (132382-43-5) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
at 110℃; for 6h; Temperature;	87.9%

5,6-dimethyl-2-mercaptobenzimidazole (3287-79-4) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With rose bengal; water; oxygen; sodium chloride In N,N-dimethyl-formamide at 25℃; for 48h; Irradiation; Green chemistry;	87%

carbon dioxide (124-38-9) + 4,5-dimethyl-2-nitrobenzenamine (6972-71-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With palladium 10% on activated carbon; phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 70℃; under 7500.75 Torr; for 15h;	84%
With gold on titanium oxide; hydrogen In 1-methyl-pyrrolidin-2-one at 100℃; under 60006 Torr; for 12h; Sealed tube; Green chemistry;	81%

carbon dioxide (124-38-9) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + C10H10N2O

Conditions	Yield
With phenylsilane at 50℃; under 22502.3 Torr; for 3h; Pressure; Autoclave;	A 78% B 11%

2-methoxy-ethanol (109-86-4) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With oxygen; toluene-4-sulfonic acid In water at 110℃; Sealed tube;	77%

D-Glucose (2280-44-6) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With tert.-butylhydroperoxide; trifluorormethanesulfonic acid; water at 100℃; for 1h; Sealed tube;	75%

methanol (67-56-1) + 4,5-dimethyl-2-nitrobenzenamine (6972-71-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 1,5,6-trimethylbenzimidazole (1128-27-4)

Conditions	Yield
With Cu-Zn-PMO at 250℃; for 3h; Sealed tube; Supercritical conditions; Green chemistry;	A 73% B n/a

tert-butylisonitrile (119072-55-8, 7188-38-7) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile at 70℃; for 24h;	60%

1-Amino-5,6-dimethylbenzimidazole (78288-57-0) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + Bis-(5,6-dimethyl-benzoimidazol-1-yl)-diazene (127845-08-3)

Conditions	Yield
With bromine; sodium carbonate In water at 0 - 5℃; for 1h;	A 55% B 10%

dimethyl sulfoxide (67-68-5) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With ammonium acetate; water at 140℃; for 10h; Inert atmosphere; Schlenk technique;	42%
With ammonium acetate In water at 140℃; for 11h; Schlenk technique; Inert atmosphere;	42%

N-D-ribityl-4,5-dimethyl-1,2-phenylenediamine (64598-64-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
With oxygen In water at 20℃; for 96h;	8%
With potassium hexacyanoferrate(III)

D-ribose 5-phosphate (3615-55-2, 7591-07-3, 13137-52-5, 66768-39-6, 69881-36-3, 69881-39-6, 136376-80-2, 136376-83-5, 136376-85-7, 136376-88-0, 136376-89-1, 4300-28-1) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 1-(5,6-dimethyl-2,3-dihydro-2H-benzimidazol-2-yl)-butane-1,2,3,4-tetrol 4-O-phosphate

Conditions	Yield
With 4-morpholineethanesulfonic acid In water at 37℃; pH=6;

N-(ribityl),N'-(Boc)-diamino-4,5-dimethylbenzene (569343-11-9) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
Stage #1: N-(ribityl),N'-(Boc)-diamino-4,5-dimethylbenzene With hydrogenchloride In water Stage #2: With sodium hydroxide In water at 20℃; for 5h; pH=7 - 8;
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 3 h / 20 °C 2: oxygen / water / 96 h / 20 °C View Scheme

4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 82 percent / NaHCO3 / H2O; tetrahydrofuran / 12 h 2.1: 85 mg / H2 / Pd(OH)2 / methanol / 2 h 3.1: HCl / H2O 3.2: NaOH / H2O / 5 h / 20 °C / pH 7 - 8 View Scheme
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate / 1,4-dioxane; water / 3 h / 20 °C 2: sodium cyanoborohydride / methanol / 48 h / Inert atmosphere; Reflux 3: hydrogenchloride / water / 3 h / 20 °C 4: oxygen / water / 96 h / 20 °C View Scheme

(2-amino-4,5-dimethyl-phenyl)-carbamic acid tert-butyl ester (371158-46-2) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 85 mg / H2 / Pd(OH)2 / methanol / 2 h 2.1: HCl / H2O 2.2: NaOH / H2O / 5 h / 20 °C / pH 7 - 8 View Scheme
Multi-step reaction with 3 steps 1: sodium cyanoborohydride / methanol / 48 h / Inert atmosphere; Reflux 2: hydrogenchloride / water / 3 h / 20 °C 3: oxygen / water / 96 h / 20 °C View Scheme

C17H16N2O2 → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
In methanol at 20℃;

4-amino-o-xylene (95-64-7) → 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.17 h / 55 °C 2: nitric acid / dichloromethane / 2 h / 15 - 25 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 10 h / 20 °C 4: 6 h / 110 °C View Scheme

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + (E)-11-(2-chloroethylidene)-6,11-dihydrodibenzoxepin-2-carboxylic acid methyl ester (127167-47-9) → (E)-11-<2-(5,6-dimethyl-1-benzimidazoyl)ethylidene>-6,11-dihydrodibenzoxepin-2-carboxylic acid methyl ester (127165-95-1)

Conditions	Yield
In N,N-dimethyl-formamide; toluene for 3h; Heating;	100%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + bromocyane (506-68-3) → 1-Cyano-5,6-dimethylbenzimidazole

Conditions	Yield
With trimethylamine Ambient temperature;	100%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 1-(halomethyl)-3,5-dimethylbenzene → 1-(3,5-dimethylbenzyl)-5,6-dimethyl-1H-benzo[d]imidazole

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With potassium hydroxide In ethanol at 20℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 1-(halomethyl)-3,5-dimethylbenzene In ethanol for 25h; Reflux; Schlenk technique; Inert atmosphere;	100%
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole In ethanol at 20℃; for 1h; Inert atmosphere; Schlenk technique; Alkaline conditions; Stage #2: 1-(halomethyl)-3,5-dimethylbenzene In ethanol at 80℃; Schlenk technique; Inert atmosphere;	93%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + C13H15N2O(1+)*BF4(1-) → 4'-(5,6-Dimethyl-benzoimidazol-1-yl)-2,6,3'-trimethyl-4'H-[1,1']bipyridinyl-4-one (77487-30-0)

Conditions	Yield
With sodium methylate In methanol; acetonitrile at 20℃; for 0.5h;	99%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + bis(trimethylsilyl)acetylenetitanocene → C76H76N8Ti4

Conditions	Yield
In toluene at 60℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;	99%

o-fluorobromobenzene (1072-85-1) + 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) → 1-(2-bromophenyl)-5,6-dimethylbenzimidazole

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 150℃;	99%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + G (118-00-3) → (β-D-ribofuranosyl)-5,6-dimethylbenzimidazole (13082-84-3)

Conditions	Yield
for 1.5h; purine nucleoside phosphorylase of whole cells of E. coli BMT 1D/1A;	98%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2'-Deoxyguanosine (961-07-9) → 1-(5,6-dimethyl-benzoimidazol-1-yl)-β-D-erythro-1,2-dideoxy-pentofuranose (4600-72-0)

Conditions	Yield
for 1.5h; purine nucleoside phosphorylase of whole cells of E. coli BMT 1D/1A;	98%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + isoflavone (574-12-9) → 2-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)-3-phenyl-4H-chromen-4-one

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide at 80℃; regioselective reaction;	98%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) → 5,6-Dimethyl-n-nitrobenzimidazol (21472-08-2)

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With tert-butyl methyl ether; nitric acid In tetrahydrofuran at 0℃; Stage #2: With sulfuric acid In dichloromethane at 0 - 5℃; for 1h; Further stages.;	97%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + isopropyl bromide (75-26-3) → 1,3-diisopropyl-(5,6-dimethyl)benzimidazolium bromide (1435268-00-0)

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With potassium carbonate In acetonitrile at 20℃; for 1h; Stage #2: isopropyl bromide In acetonitrile for 96h; Reflux;	97%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + cyclohexane-1,2-epoxide (286-20-4) → 1-(2-hydroxycyclohexyl)-5,6-dimethylbenzimidazole (1184249-74-8)

Conditions	Yield
In neat (no solvent) at 70℃; for 12h;	97%
In neat (no solvent) at 70℃; for 12h;	78%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2-bromo-N-(4-methoxyphenyl)benzenesulfonamide (1178125-92-2) → C22H19N3O3S

Conditions	Yield
With copper(l) iodide; oxygen; sodium methylate; L-proline In N,N-dimethyl-formamide at 130℃; for 24h; Schlenk technique; Sealed tube;	97%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + (2,3,4,5,6-pentamethylbenzyl) halide → 5,6-dimethyl-1-(2,3,4,5,6-pentamethylbenzyl)-1H-benzo[d]imidazole

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With potassium hydroxide In ethanol at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: (2,3,4,5,6-pentamethylbenzyl) halide In ethanol at 80℃; Inert atmosphere; Schlenk technique;	97%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 1-(halomethyl)-2,3,4,5,6-pentamethylbenzene → 5,6-dimethyl-1-(2,3,4,5,6-pentamethylbenzyl)-1H-benzo[d]imidazole

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole In ethanol at 20℃; for 1h; Inert atmosphere; Schlenk technique; Alkaline conditions; Stage #2: 1-(halomethyl)-2,3,4,5,6-pentamethylbenzene In ethanol at 80℃; Schlenk technique; Inert atmosphere;	97%
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With potassium hydroxide In ethanol at 20℃; for 1h; Stage #2: 1-(halomethyl)-2,3,4,5,6-pentamethylbenzene In ethanol at 80℃; for 24h;

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + N-phenacyl-p-toluidine (4831-18-9) → 2-(5,6-Dimethyl-1H-benzo[d]imidazol-1-yl)-1-phenyl-2-(p-tolylimino)ethan-1-one

Conditions	Yield
With di-tert-butyl peroxide; copper(l) chloride In chlorobenzene at 110℃;	97%
With di-tert-butyl peroxide; copper(l) chloride In chlorobenzene at 110℃; for 2h;	77%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2,3,4,5,6-pentamethylbenzyl chloride (484-65-1) → 5,6-dimethyl-1-(2,3,4,5,6-pentamethylbenzyl)-1H-benzo[d]imidazole

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With potassium hydroxide In ethanol at 20℃; for 0.25h; Stage #2: 2,3,4,5,6-pentamethylbenzyl chloride In ethanol at 20℃; for 17h; Reflux;	97%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + carbonochloridic acid 1-chloro-ethyl ester (50893-53-3) + allyltributylstanane (24850-33-7) → 2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-5,6-dimethylbenzimidazoline

Conditions	Yield
With triethylamine In dichloromethane 0 deg C to room temp., 3 h;	96%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + C14H14BrNO2S → C23H21N3O2S

Conditions	Yield
With copper(l) iodide; oxygen; sodium methylate; L-proline In N,N-dimethyl-formamide at 130℃; for 24h; Schlenk technique; Sealed tube;	96%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2-bromo-N-p-tolylbenzenesulfonamide (1183123-34-3) → C22H19N3O2S

Conditions	Yield
With copper(l) iodide; oxygen; sodium methylate; L-proline In N,N-dimethyl-formamide at 130℃; for 24h; Schlenk technique; Sealed tube;	96%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2-chloro-5-fluoropyrimidine (62802-42-0) → 1-(5-fluoropyrimidin-2-yl)-5,6-dimethyl-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 70℃; for 24h; Inert atmosphere;	96%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole → 6-((5,6-dimethyl-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole

Conditions	Yield
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;	96%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2,5-difluoropyrimidine (17573-84-1) → 1-(5-fluoropyrimidin-2-yl)-5,6-dimethyl-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 70℃; for 24h; Schlenk technique;	96%

isochromane (493-05-0) + 5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) → C18H18N2O

Conditions	Yield
With [bis(acetoxy)iodo]benzene In 1,2-dichloro-ethane at 20 - 80℃; for 6h; Schlenk technique;	96%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + methyl iodide (74-88-4) → 1,5,6-trimethylbenzimidazole (1128-27-4)

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether In tetrachloromethane for 30h; Ambient temperature;	95%
With sodium hydroxide In water; acetonitrile at 0 - 20℃; for 72h; Inert atmosphere;	65%
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With sodium hydroxide In tetrahydrofuran for 0.166667h; Stage #2: methyl iodide In tetrahydrofuran at 20℃;
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With sodium hydride In mineral oil at 0 - 20℃; for 0.5h; Schlenk technique; Stage #2: methyl iodide In mineral oil at 20℃; Schlenk technique;

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) → 1H-benzimidazole-5,6-dicarboxylic acid (10351-75-4)

Conditions	Yield
With potassium permanganate In water; tert-butyl alcohol at 70℃; for 0.5h;	95%
With potassium permanganate In tert-butyl alcohol at 75℃; for 1.5h;	60%
With potassium permanganate at 75℃;	55%
With potassium permanganate In water; tert-butyl alcohol at 70℃;	48%

Upstream product

• 64-18-6 formic acid 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 3615-55-2 D-ribose 5-phosphate 
• 610-23-1 4,5-dimethyl-1,2-dinitrobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 144-62-7 oxalic acid 
• 67-68-5 dimethyl sulfoxide 
• 4252-31-7 N-formylbenzamide 
• 132382-43-5 2-amino-4,5-dimethylformanilide 
• 6639-60-7 N-(3,4-dimethylphenyl)formamide 
• 95-64-7 4-amino-o-xylene 
• 2280-44-6 D-Glucose 
• 3287-79-4 5,6-dimethyl-2-mercaptobenzimidazole 
• 67-56-1 methanol 

Downstream Products

• 132-13-8 5,6-dimethyl-α-D-ribofuranosylbenzimidazole 
• 141472-93-7 5,6-Dimethyl-1-(3-methyl benzyl)-1H-benzo[d]imidazole 
• 141211-39-4 5,6-Dimethyl-1-(4-methyl-benzyl)-1H-benzoimidazole 
• 368450-55-9 methyl 2,3-O-bis[4-(N-(5,6-dimethyl)benzimidazolyl)butyl]-4,6-O-benzylidene-α-D-glucopyranoside 
• 941306-85-0 5,6-dimethyl-1-[4-(phenylseleno)butyl]-1H-benzimidazole 
• 941306-84-9 5,6-dimethyl-1-[3-(phenylseleno)propyl]-1H-benzimidazole 
• 941306-86-1 5,6-dimethyl-1-[5-(phenylseleno)pentyl]-1H-benzimidazole 
• 317824-37-6 2-[(S)-1-Phenylethylamino]-4-[5,6-dimethylbenzimidazol-1-yl]pyrimidine 
• 10351-76-5 6-methyl-1H-benzo[d]imidazole-5-carboxylic acid 
• 1096706-52-3 N-(2,4-dichlorobenzyl)-2-(5,6-dimethyl-1H-benzoimidazol-1-yl)-N-(2-(5,6-dimethyl-1H-benzoimidazol-1-yl)ethyl)ethanamine 
• 1352222-23-1 1-(4-bromophenyl)-5,6-dimethyl-1H-benzo[d]imidazole 
• 1535186-87-8 C₁₆H₁₂FN₃ 
• 1535187-12-2 C₁₆H₁₂FN₃ 
• 1571902-15-2 1-(3-(trifluoromethyl)benzyl)-5,6-dimethyl-1H-benzo[d]imidazole 

Relevant articles and documents

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Preparation method of 5, 6-dimethylbenzimidazole

The invention discloses a preparation method of 5, 6-dimethyl benzimidazole. The preparation method comprises the following four steps: preparation of N-(3, 4-dimethyl phenyl) formamide, preparation of N-(4, 5-dimethyl-2-nitrophenyl) formamide, preparation of N-(2-amino-4, 5-dimethyl phenyl) formamide, and preparation of 5, 6-dimethyl benzimidazole. The preparation method has the following beneficial effects: 1, acetylation and deacetylation used in the prior art are avoided, which is in favor of environmental protection; 2, the synthesis steps of the process are shortened, the original five-step reaction is shortened to the present four-step reaction, and the yield is improved; and 3, the purity of the intermediate is high, separation is not needed, the operation is simple, the defects and deficiencies of the preparation method reported in the literature are overcome, and the method has novelty, greater positive progress effect and practical application value.

A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles

Chemocatalytic upgrading of the greenhouse gas CO2 to valuable chemicals and biofuels has attracted broad attention in recent years. Among the reported approaches, N-formylation of CO2 with an amine is of great significance due to its versatility in the construction of N-containing linear and cyclic skeletons. Herein, a stable N-heterocyclic carbene-carboxyl adduct (NHC-CO2) was facilely prepared and could be used as a recyclable zwitterionic catalyst for efficient CO2 reductive upgrading via either N-formylation or further coupling with cyclization under mild conditions (25 °C, 1 atm CO2) using hydrosilane as a hydrogen source. More than 30 different alkyl and aromatic amines could be transformed into the corresponding formamides or benzimidazoles with remarkable yields (74%-98%). The electronic effect of the introduced substituent on NHC-CO2 was found to evidently affect the thermostability and nucleophilicity of the zwitterionic catalyst, which is directly correlated with its catalytic activity. Moreover, NHC-CO2 could supply CO2 by in situ decarboxylation at a specific temperature that is dependent on the introduced substituent type. Experimental and computational studies showed that the carboxyl species on NHC-CO2 was not only a nucleophilic center, but also a C1 source which rapidly captures or substitutes ambient CO2 during hydrosilylation. In addition, a simple and green conceptual process was designed for the product purification and catalyst recycling, with a good feasibility for small-scale production.