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CAS No. : | 729-13-5 | MDL No. : | MFCD00225481 |
Formula : | C13H9N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TVNHSLVVOOKWHG-UHFFFAOYSA-N |
M.W : | 239.23 | Pubchem ID : | 3720818 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; iron; In ethanol; water;Reflux; | General procedure: Iron powder (3-4 mmol) and 6 N HCl solution (1 ml) were added to the solution of the nitro derivatives (1 mmol) in EtOH (5 ml) and the mixture was heated to reflux under nitrogen for 3-5 h. After cooling to room temperature, the suspension was diluted with EtOAc (20 ml); a solution of 6 M NaOH (20 ml) was added until basic pH and the layers were separated. The aqueous layer was extracted with AcOEt(2 X 20 ml) and the combined organic layers were washed with brine,dried over anhydrous Na2SO4, filtered and evaporated under vacuum.The crude product was purified by chromatography on silica gel(eluent: EtOAc/Hexane 6:4 v/v or CHCl3/MeOH 9.5:0.5 v/v to 9:1 v/v)or triturated with diethyl ether. |
With hydrogenchloride; acetic acid; zinc; In diethyl ether; at -2℃; for 1h;Reflux; | To a solution of compound 8 (5 mmol) in diethyl ether (30 mL) were added 9:1 acetic acid : HCl (15 mL) and zinc dust (2.7 g, 40 mmol). The reaction mixture was stirred for 30 min at room temperature then refluxed for 30 min. The mixture was decanted from the reaction flask and the zinc was washed with ether. The combined organic layer was then washed with water dried over anhydrous sodium sulfate. The excess of solvent was removed under reduced pressure and the residue was subjected to column chromatography over silica gel 60-120 using dichloromethane/ methanol (9:1, v/v) as the eluting solvent system, to render the pure products (9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 98 % Chromat. 2: 94% | In ethanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With diphosphorus tetraiodide In acetonitrile at 80℃; Sealed tube; Inert atmosphere; | General procedure for synthesis of 2-aryl-benzimi-dazoles/2-aryl-benzoxazoles/2-aryl-benzothiazoles: General procedure: To amixture of ortho-substituted (-NH 2 or -SH or -OH) anilines(1 mmol) and aryl acids (1 mmol) in acetonitrile (2 mL) in asealed tube (10 mL) was added diphosphorus tetraiodide (0.2mmol) under nitrogen atmosphere. Then, the tube was cappedand the mixture heated in an oil bath at 80 °C with stirringuntil the reaction was complete as monitored by TLC. Afterbeing cooled to room temperature, the reaction was quenchedwith aqueous NaHCO 3 solution and extracted with ethyl acetatethree times. The combined organic layer was washed withwater and brine and then dried over anhydrous Na 2 SO 4 . Thesolvent was removed under reduced pressure and the residuewas purified by chromatography on silica gel, eluting withpetroleum ether/ethyl acetate, to afford the correspondingproduct. The products obtained were known compounds andwere identified by melting point and 1 H NMR spectroscopy.The spectral data were compared with the literature values.2-Phenyl-1H-benzimidazole (Table-2, entry 1): m.p.:290-293 °C (Lit. [21] 292-294 °C); IR (KBr, ν max , cm -1 ): 3450,3045, 1620, 1580, 1458; 1 H NMR (400 MHz, DMSO-d 6 ): δ7.08-7.14 (m, 2H), 7.31-7.5 (m, 5H), 7.96 (d, 2H), 12.80 (s,1H); 13 C NMR (DMSO-d 6 , TMS): δ 116.5, 123.1, 127.4, 128.6,129.5, 130.7, 139.0, 152.7; MS (ESI) m/z: [M+H] + 195.1. |
82% | With Amberlyst-15 In water at 90℃; for 1.5h; Irradiation; | General procedure for the preparation of compound 3-5 General procedure: To a solution of o-phenylenediamine 1a, o-amino phenol 1b or o-amino thiophenol 1c (1.0 mmol) and aromatic acid (2, 1.2 mmol) in water (5 mL) was added Amberlyst-15 (10%, w/w) and the mixture was irradiated with ultrasound (40 KHz) continuously at 90 °C till the completion of the reaction(monitored by TLC) as indicated in Table 3. The solid separated was filtered, washed with diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid obtained was purified by recrystallization (column chromatography infew cases) to afford the desired products 3, 4 or 5. |
78% | Stage #1: 4-nitro-benzoic acid With borane-THF In tetrahydrofuran; toluene at 20℃; for 0.5h; Cooling with ice; Stage #2: 1,2-diamino-benzene In tetrahydrofuran; toluene for 12h; Reflux; |
62% | at 200℃; for 2h; | |
62% | With boric acid In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Reflux; | |
48% | In o-xylene for 2h; Heating; | |
40.5% | In ethanol at 100℃; for 8h; | General procedure for synthesis of ligands (LS1-LS5): General procedure: All substituted benzimidazole ligands were prepared by the previously reported procedure [17]. o-Phenylenediamine (0.25 mol) and appropriate carboxylic acid (0.34 mol) was heated on an oil bath at 100 C for 8 h. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled and its pH was adjusted between 7-8 using 10% NaOH solution. The crude benzimidazole was filtered and washed with ice-cold water. The crude product was dissolved in 40 mL of boiling water and 2 g of carbon was added and digested for 15 min. The solution was filtered while hot, cooled the filtrate to about 10 C. The pure product obtained was filtered, washed with 25 mL of cold water and dried (Scheme-I). |
In acetic acid for 0.25h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With air; Fe3O4 fabricated ZnO doped WO3 nanoparticle In ethanol at 20℃; for 2.5h; Irradiation; Green chemistry; | |
98% | With coomassie brilliant blue (CBB) coated on n-propylamine functionalized W-ZnO nanoparticles In ethanol at 25℃; for 2h; UV-irradiation; Green chemistry; | |
94% | With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper chloride (I) In neat (no solvent) at 20℃; for 11h; Green chemistry; |
93% | With Ni0.5Co0.5Fe2O4 supported on arginine-grafted graphene oxide nanocomposite; air In acetonitrile at 80℃; | |
91% | In neat (no solvent) at 150℃; for 24h; Green chemistry; | General procedure General procedure: Reactions were performed in a magnetically stirred round bottomed flask fitted with acondenser and placed in a temperature controlled oil bath. 1,2-Diamine (2 mmol)was added to alcohol (3 mmol) and the reaction mixture was allowed to stir at 135°C in an open (air) atmosphere. After disappearance of the diamine (reaction was monitored by TLC)or after the appropriate time, the reaction mixture was cooled to roomtemperature. The crude residue was further purified by column chromatography using silica gel (100-200 mesh) to afford pure products. All the products wereidentified on the basis of NMR and mass spectral data |
90% | Stage #1: 4-Nitrobenzyl alcohol With iodine; potassium carbonate In <i>tert</i>-butyl alcohol at 50℃; for 2h; Stage #2: 1,2-diamino-benzene In <i>tert</i>-butyl alcohol at 70℃; for 3h; Further stages.; | |
90% | With copper(II) bis(2,4-pentanedionate) In dimethyl sulfoxide at 20℃; for 6h; | 6 Example 6: Add o-phenylenediamine (1.0 mmol), 4-nitrobenzyl alcohol (1.2 mmol), Cu (acac) 2 (0.02 mmol) in sequence to the reaction tube, and then add 2 mL of solvent DMSO,The reaction was carried out at room temperature for 6 hours. After the reaction was completed, the reaction solution was concentrated.The corresponding product was obtained by column chromatography and the separation yield was 90%. |
88.2% | With N-hydroxyphthalimide; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene at 100℃; for 10h; Green chemistry; | |
86% | With Fe2(SO4)3; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In neat (no solvent) at 110℃; for 20h; Green chemistry; | Typical procedure for aerobic oxidative synthesisof benzimidazoles, benzoxazoles, or benzothiazoles General procedure: A mixture of 6 mmol of the alcohol or the amine and5 mmol o-phenylenediamine, o-aminophenol or o-aminothiophenol,10 mol % Fe2(SO4)3, 10 mol % TEMPO wasprepared in a 10 ml three-necked flask, and then stirred inopen air at 110 °C for several hours, The reaction progresswas monitored by TLC. When the final reaction mixturecooled to room temperature, the crude products was directlypurified by column chromatography on silica gel using hexane/ethyl acetate (7:3) as eluent to afford the pure product. |
86% | With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium-t-butoxide; oxygen In toluene at 80℃; for 10h; | |
85% | With copper(II)-manganese(II) bimetallic complex immobilized on magnetite nanoparticles; air In neat (no solvent) at 70℃; for 4h; Green chemistry; | 2.5 General Procedure for Domino One-Pot Preparation of Benzimidazole and Biginelli Derivatives Catalyzed by Fe3O4(at)Cu-Mn General procedure: The one-pot synthesis of benzimidazole carried out in around-bottom flask with benzyl alcohol (1.2mmol) and ortho phenylenediamine (1.0mmol) using Fe3O4Cu-Mn catalyst (0.008g, 0.280mol% Cu, 0.078mol% Mn), under solvent-free and aerobic conditions at 70°C. The reaction mixture was monitored with TLC. Upon reaction completion, the catalyst was magnetically separated, then the product was extracted to dichloromethane (3 × 5mL).The organic layers were combined, dried over Na2SO4 and purified by silica-gel column chromatography (n-hexane:EtOAc = 10: 5). |
85% | In acetonitrile Irradiation; Inert atmosphere; | 2.3 Catalytic reactions The photocatalytic synthesis of benzimidazole was investigaded by using Co-TiO2 catalyst under solar light irradiation. In a typical experiment, orthophenylene diamine (0.226g, 1.66mmol) was dissolved (5ml solution of benzyl alcohol (0.213g, 1.75mmol) in acetonitrile (5ml), and 50mg of photocatalyst was added to 100ml quartz photo reactor. Prior to photoirradiation, the suspensions were magnetically stirred while the reactor was purged with nitrogen gas for 20min to generate inert atmosphere in the photo reactor. The photocatalytic reaction was carried out under solar light irradiation and the reaction mixture was magnetically stirred during the entire period (8h) of experiment. The progress of the reaction was monitored with TLC. After completion of the reaction, the photocatalyst was separated by centrifugation. The mixture was treated with ethyl acetate and then concentrated in vacuo. The residue was purified by silica-gel column chromatography with ethyl acetate/hexane (1:4) to afford the product. |
85% | With oxygen In N,N-dimethyl-formamide at 120℃; for 8h; | |
81% | With anhydrous sodium carbonate In neat (no solvent) at 120℃; Green chemistry; | Catalyst Usage for the dehydrogenative coupling General procedure: Typically, o-phenylenediamine (1.3 mmol) or 2-aminothiophenol (1 mmol), benzyl alcohols (1 mmol), Na2CO3 (20 mol%), and Pd-NPs/Cu2(BDC)2(DABCO) (20 mg, 0.01 mol%) were added to a round-bottom flask. The reaction mixture was heated to 120 °Cand stirred at for the appropriate time in air (TLC monitoring). Ethyl acetate was added to the reaction mixture and catalyst was filtered. For the purification of impure products, chromatography on silica gel was performed (EtOAc:Hep. (1:6)). The entire products characterized by melting point, CHN, 1H-NMR and13C-NMR spectroscopy. |
68% | Stage #1: 4-Nitrobenzyl alcohol With N-hydroxyphthalimide; Mo72V30; oxygen In ethyl acetate at 70℃; for 8h; Stage #2: 1,2-diamino-benzene In ethyl acetate | |
67% | With cobalt sulphate heptahydrate; lithium perchlorate; trifluoroacetic acid In water monomer; acetonitrile at 50℃; for 6h; Electrochemical reaction; | |
With C89H124Cl3IrN2P2Ru; sodium hydroxide In 1,4-dioxane at 110℃; for 18h; Inert atmosphere; Schlenk technique; | 19 Embodiment 19 2 - nitro phenyl -1HSynthesis of benzimidazole -: in an inert gas (such as high-pure nitrogen) under the protection, to 10 ml of the reaction tubes to join Schlek 0.04mmol ruthenium iridiumdifferent nuclear ring metal compound 21, 1.0mmol O-phenylendiamine, 1.7mmol P-nitro benzyl alcohol, 0.7mmol sodium hydroxide and 3 ml of dioxane, replace the nitrogen reaction tube 3 times, then in the oil bath for magnetic stirring under heating to 110 °C, reaction reflux 18 hours. To remove the oil bath, water bath to room temperature; to responds fluid Canada 3 ml water, for 5 ml of dichloromethane extraction three times, and the combined organic phase with anhydrous MgSO4Drying 30 minutes, filtered; the filtrate using a rotary evaporator concentrated, petroleum ether/ethyl acetate to residual liquid as developing agent, silica gel thin layer chromatography separation, to obtain the pure product 2 - nitro phenyl -1H- Benzimidazole, yield 81%. | |
With N-hydroxyphthalimide at 70℃; for 3h; | 2.2.1 General Procedure for Synthesis of Benzimidazole from Benzyl Alcohols and o-Phenylenediamines General procedure: To a mixture of benzyl alcohol (1.2mmol), 1,2-phenylenediamine(1mmol) and NHPI (5mol%) in a glass test tube(10cm tall × 1cm diameter) was added TiO2/AA/Co nanocatalyst(0.06mol%) and the reaction mixture was heatedat 70°C under air, visible light and solvent free conditions.The reaction progress was monitored by TLC. After 3h,ethanol (5mL) was added to the mixture and then TiO2/AA/Co nanocatalyst (solid phase) was separated by centrifugingfollowed by decantation (3 × 5mL ethanol). Desired product(liquid phase) was extracted by plate chromatography elutedwith n-hexane/EtOAc (10/2). Assignments of products weremade by 1H NMR spectral data in comparison with authenticsamples. | |
54.1 %Chromat. | With oxygen In acetonitrile at 27.8℃; for 24h; Irradiation; Green chemistry; | |
With porous borocarbonitride In N,N-dimethyl-formamide for 48h; Inert atmosphere; Irradiation; Green chemistry; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere; | General experimental procedure General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere; | General experimental procedure General procedure: A flask was charged with Cu2O (14 mg, 0.1 mmol), Cs2CO3 (977 mg, 3 mmol), o-haloaniline (1 mmol) and amidine hydrochloride (1.5 mmol) in 2 mL DMF under nitrogen atmosphere. The mixture was stirred at room temperature and DMEDA (20 mL, 0.2 mmol) was added via syringe. The reaction mixture was then stirred in a preheated oil bath at 140 C for 16 h, and then cooled to room temperature. The inorganic salt was filtered off and ethyl acetate, water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4, and concentrated in vacuum.The residue was purified by column chromatography on silica gelusing petroleum ether/ethyl acetate as eluent to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; for 8h; | Synthesis of benzimidazole derivatives 3a-h General procedure: A mixture of 1-fluoro-2-nitrobenzene (1) (0.141 g,1.0 mmol), the appropriate benzamidine hydrochloride 2a-h (1.0 mmol), CuBr (0.029 g, 0.2 mmol), and K2CO3 (0.276 g,2.0 mmol) in dry DMSO (3.0 ml) was heated in a round bottom flask for 8 h at 120°C. After the reaction was complete (TLC), the mixture was cooled, quenched with water (20 ml), and extracted with EtOAc (3 × 20 ml). The extract was washed with 20% aqueous NaCl solution, dried over Na2SO4, and concentrated under reduced pressure.The residue was purified by column chromatography using petroleum ether - ethyl acetate, 4:1, as eluent to afford the pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In methanol; for 10h;Reflux; Inert atmosphere; | General procedure: The ruthenium precursor was prepared in accordance with the previously reported method [18]. The precursor was synthesized with the reaction of ruthenium trichloride trihydrate witha methanolic solution of tryphinylphosphine in excess and refluxed for 8 h under nitrogen,which gives the black precipitate of <strong>[15555-77-8][RuCl2(PPh3)4]</strong> (MR), washed with diethylether and dried in vaccuo. Triphenylphosphine ligands are easily replaced by other ligands in the precursor complexes [19]. The complexes of general formula [Ru(PPh3)2(BZM)2Cl2] were synthesizedby the reaction of ruthenium dichlorotetratriphenylphosphine with different substituted benzimidazole in 1:2 molar ratio in methanol. Further, RuCl2(pph3)4 (0.265 g, 1 mmol) was added to a methanolic solution of the ligands, 2 mmol (LS1, 0.328g;LS2, 0.554 g; LS3, 0.478 g; LS4, 0.146 g; LS5, 0.456 g). The solutions were refluxed for 10 h in nitrogen and reduced the volume, thus a microcrystalline precipitate was obtained (Scheme-I). The analytical data for these complexes are in good agreement with their respective molecular formula. The new complexes were formed by the substitution of two triphenylphosphine complexes by benzimidazole which indicates the labile nature of phosphine bond and addition of Nitrogen based ligands, this is due to the better sigma (σ) donating ability of the nitrogen bases to that of triphenylphosphine [20]. The complexes were sparingly soluble in organic solvent as acetone, alcohol and methanol but soluble in DMSO/DMF. The molar conductivities values were 0.055-0.163 ohm-1 cm2 mol-1. The observed values indicates the non-electrolytic nature of complexes. |
Tags: 729-13-5 synthesis path| 729-13-5 SDS| 729-13-5 COA| 729-13-5 purity| 729-13-5 application| 729-13-5 NMR| 729-13-5 COA| 729-13-5 structure
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H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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