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[ CAS No. 23309-16-2 ] {[proInfo.proName]}

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Chemical Structure| 23309-16-2
Chemical Structure| 23309-16-2
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Product Details of [ 23309-16-2 ]

CAS No. :23309-16-2 MDL No. :MFCD01795851
Formula : C9H7N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HESJLLCGKVDGIB-UHFFFAOYSA-N
M.W : 189.17 Pubchem ID :821062
Synonyms :

Safety of [ 23309-16-2 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 23309-16-2 ]

* 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.

  • Downstream synthetic route of [ 23309-16-2 ]

[ 23309-16-2 ] Synthesis Path-Downstream   1~62

  • 1
  • [ 288-32-4 ]
  • [ 1493-27-2 ]
  • [ 23309-16-2 ]
YieldReaction ConditionsOperation in experiment
37% With triethylamine; In neat (no solvent); at 140℃; for 9h; General procedure: A mixture of 1-fluoro-2-nitrobenzene 1 (1.5 g, 11 mmol), 2 (16 mmol), and triethylamine (0.6 g, 5.5 mol) was stirred at 140 C for 9 h. After completion of the reaction as indicated by TLC, the mixture was cooled to 20 C and filtered. The filter cake was washed with water and anhydrous ethanol until the pH of filtrate reached 7, then dried in vacuum to obtain compound 3.
With potassium carbonate; In water; acetonitrile; A. 1-(2-Nitrophenyl)-1H-imidazole To a solution of 2-fluoronitrobenzene (12 g, 85 mmol) in 200 mL acetonitrile was added imidazole (8.6 g, 127 mmol) and potassium carbonate (23 g, 170 mmol). The reaction was heated to reflux for 18 h then cooled to room temperature and filtered through celite. The mixture was concentrated in vacuo followed by the addition of water. The aqueous solution was extracted with dichloromethane. Concentration of the organic layer gave a yellow solid which was refluxed in diethyl ether. The ether was cooled to room temperature and the solid filtered to give 14.39 g (89.9%) of 18A.
With sodium hydroxide; In dimethyl sulfoxide; at 20℃; General procedure: To a well-stirred solution of N- heterocycles 1a-c (1.0mmol) in 1.0 ml of DMSO, NaOH (1.0 equiv) and 2-floronitrobenzene 2 was added slowly. The reactionmixture was stirred vigorously for 1-1.5 h at r. t. till no more starting material wasdetectable by TLC analysis. After that reaction mixture was extracted withethyl acetate and water and dried over Na2SO4. Thesolvent was evaporated in vacuo and the crude was purified by columnchromatography (hexane and ethylacetate) to afford the desired product in goodyields. Compounds 3b-c was previouslyreported
  • 2
  • [ 23309-16-2 ]
  • [ 26286-54-4 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 2327.23 Torr; General procedure: To a well-stirred solution of alkyl substituted <strong>[23309-16-2]1-(2-nitrophenyl)-1H-imidazole</strong> 3a-c (1.0 mmol) in 25 mlof absolute ethanol, of 10% Pd/C (20 mol %) wasadded. The reaction mixture was stirred for 2-3 h at r. t. underhydrogen atmosphere at 45 psi. Then the reaction mixture was filtered with aidof celite and the filtrate was evaporated in vacuo to obtain the desiredamines. Compounds 4b-c was previouslyreported
  • 4
  • [ 288-32-4 ]
  • [ 88-73-3 ]
  • [ 23309-16-2 ]
YieldReaction ConditionsOperation in experiment
75.1% With copper(II) 29H,31H-tetrabenzo[b,g,l,q]porphine; potassium hydroxide; In dimethyl sulfoxide; at 90℃; for 24h; General procedure: In a typical experiment, imidazole (1.2 mmol), aryl halide (1.0 mmol), catalyst, and base (2.0 mmol) were added to a hydrothermal reactor (20 mL). The mixture was heated to the desired temperature with stirring. After the completion of the reaction and cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 15mL). The combined organic extracts were dried with anhydrous Na2SO4 and the obtained product was purified by column chromatography on silica gel using dichloromethane: methanol (100:1, v/v) as the eluent.
  • 7
  • [ 23309-16-2 ]
  • [ 1043391-18-9 ]
  • 8
  • [ 288-32-4 ]
  • [ 577-19-5 ]
  • [ 23309-16-2 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Catalytic behavior; General procedure: A mixture of aryl halide (2.4 mmol) and Cs2CO3(4.0 mmol,0.650 g), nitrogen-containing heterocycle (2.0 mmol), dry DMF(3 mL) solvent and catalyst was stirred at 100C in an oil bath under air. After cooling to room temperature, catalyst was first separated out by centrifugation and the liquid part was extracted with water and diethylether (2 × 15 mL). The organic layers thus collected were combined and washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified bycolumn chromatography on silica gel (mesh 60-120) using an n-hexane/ethylacetate mixture as the eluent to collect the desiredproduct. The product was analyzed by 1H and13C NMR and mass spectroscopy.
90% With copper(I) 2-hydroxy-3-methylbenzoate; potassium carbonate; In dimethyl sulfoxide; at 110℃; for 3h; General procedure: A dry flask was charged with the nitrogen containing heterocycles (1.5 mmol), aryl halides (1 mmol), potassium carbonate(2 mmol) and CuMeSal (0.01 mmol) then anhydrous DMSO (5 ml) was added. The reaction mixture was stirred at 110C, open to air, for 3h , cooled to room temperature, filtered, and the precipitate was washed with DMSO (2 ml) then stirred with ice water (30 ml) and extracted with ethyl acetate (3 × 50 ml),dried over sodium sulfate and the solvent was removed under reduced pressure.The residue was purified by chromatography or recrystallization as indicated with each compound.
76% With potassium carbonate; at 120℃; for 36h; A mixture of imizadol (5.00 g, 73.4 mmol), 1-bromo-2-nitrobenzene (2.00 g, 9.9 mmol), and K2CO3 (2.05 g, 14.8 mmol) was heated at 120 C for 36 h. After cooled to r.t., the reaction mixture was extracted with dichloromethane three times. The solution was treated with MgSO4, filtered, and dried in vacuo to give crude product. The crude product was purified by chromatography (silica gel, ethyl acetate/hexane = 2/1) to obtain yellow solid (76% yield).
  • 9
  • [ 288-32-4 ]
  • 2-NO2-C6H4-X; X = I, Br [ No CAS ]
  • [ 23309-16-2 ]
  • 10
  • [ 288-32-4 ]
  • [ 609-73-4 ]
  • [ 23309-16-2 ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate; In N,N-dimethyl-formamide; at 152℃; for 18h; General procedure: To a vigorously stirred suspension of the CuNPs/MagSilica catalyst (100 mg) in DMF (6 mL) under air, K2CO3 (276 mg, 2.0 mmol) and imidazole (136 mg, 2.0 mmol) were added. The reaction mixture was stirred for 30 min and then the corresponding aryl halide (1.0 mmol) was added and the reaction flask was immersed in an oil bath at the reflux temperature of DMF (152 C). The reaction mixture was stirred at this temperature until no further conversion of the starting aryl halide was observed (TLC, GC). The catalyst was immobilized by means of a permanent magnet placed on the outer wall of the reaction flask, and washed twice with Et2O (10 mL each). Finally, the catalyst was dried under vacuum (5 Torr) for its recovery and reuse. The crude reaction mixture was evaporated under vacuum (15 Torr) and the resulting residue was purified by flash column chromatography (silica gel, hexane/AcOEt) to afford the corresponding N-aryl imidazoles (2a-j). All known compounds included in Table 1 were characterized by comparison of their chromatographic and spectroscopic data (1H, 13C NMR, and MS) either with those of the corresponding commercially available pure samples (2g) or with those described in the literature (2a,21 2b,212c,22 2d,21 2e,11a 2f,11a 2h,23 2i,24 2j25).
  • 11
  • [ 23309-16-2 ]
  • [ 1352820-79-1 ]
  • 12
  • [ 23309-16-2 ]
  • [ 1352820-80-4 ]
  • 13
  • [ 23309-16-2 ]
  • [ 1352820-82-6 ]
  • 14
  • [ 23309-16-2 ]
  • [ 1352820-83-7 ]
  • 15
  • [ 23309-16-2 ]
  • [ 1352820-41-7 ]
  • 16
  • [ 23309-16-2 ]
  • [ 1352820-42-8 ]
  • 17
  • [ 23309-16-2 ]
  • [ 1352820-44-0 ]
  • 18
  • [ 23309-16-2 ]
  • [ 1352820-46-2 ]
  • 19
  • [ 23309-16-2 ]
  • [ 1155486-44-4 ]
  • 20
  • [ 23309-16-2 ]
  • C13H15N3 [ No CAS ]
  • 21
  • [ 23309-16-2 ]
  • [ 1155482-76-0 ]
  • 22
  • [ 23309-16-2 ]
  • [ 1338382-49-2 ]
  • 23
  • [ 23309-16-2 ]
  • C12H16N3(1+)*F6P(1-) [ No CAS ]
  • 24
  • [ 23309-16-2 ]
  • C24H30AgN6(1+)*I(1-) [ No CAS ]
  • 25
  • [ 23309-16-2 ]
  • C12H15AuClN3 [ No CAS ]
  • 26
  • [ 75-30-9 ]
  • [ 23309-16-2 ]
  • [ 1428140-14-0 ]
YieldReaction ConditionsOperation in experiment
96% at 120℃; for 12h; A mixture of <strong>[23309-16-2]1-(2-nitrophenyl)imidazol</strong> (1.00 g, 5.30 mmol) and2-isopropane (4.50 g, 26.4 mmol) was heated at 100 C for 12 h.After cooled to r.t., the reaction mixture was filtered and the residuewas washed with ethyl acetate. Recrystallization from CH3OHto obtain yellow product (96% yield)
  • 27
  • [ 23309-16-2 ]
  • C13H18N3(1+)*Br(1-) [ No CAS ]
  • 28
  • [ 23309-16-2 ]
  • C13H18N3(1+)*I(1-) [ No CAS ]
  • 29
  • [ 23309-16-2 ]
  • C11H14N3(1+)*I(1-) [ No CAS ]
  • 30
  • [ 23309-16-2 ]
  • [ 1428140-16-2 ]
  • 31
  • [ 23309-16-2 ]
  • 1-(2-aminophenyl)-3-n-butylimidazolium hexafluorophosphate [ No CAS ]
  • 32
  • [ 23309-16-2 ]
  • C26H34AgN6(1+)*AgBr2(1-) [ No CAS ]
  • 33
  • [ 288-13-1 ]
  • [ 577-19-5 ]
  • [ 23309-16-2 ]
  • 34
  • [ 23309-16-2 ]
  • 3-phenylimidazo[1,2-a][1,2,3]triazolo[5,1-c]quinoxaline [ No CAS ]
  • 35
  • [ 23309-16-2 ]
  • 3-(4-methoxyphenyl)imidazo[1,2-a][1,2,3]triazolo[5,1-c]quinoxaline [ No CAS ]
  • 36
  • [ 23309-16-2 ]
  • methyl 3-(imidazo[1,2-a][1,2,3]triazolo[5,1-c]quinoxalin-3-yl)benzoate [ No CAS ]
  • 37
  • [ 23309-16-2 ]
  • 3-(thiophen-2-yl)imidazo[1,2-a][1,2,3]triazolo[5,1-c]quinoxaline [ No CAS ]
  • 38
  • [ 23309-16-2 ]
  • 3-pentylimidazo[1,2-a][1,2,3]triazolo[5,1-c]quinoxaline [ No CAS ]
  • 39
  • [ 23309-16-2 ]
  • 3-methylimidazo[1,2-a][1,2,3]triazolo[5,1-c]quinoxaline [ No CAS ]
  • 40
  • [ 288-32-4 ]
  • [ 5570-19-4 ]
  • [ 23309-16-2 ]
YieldReaction ConditionsOperation in experiment
35% With copper(I) 2-hydroxy-3-methylbenzoate; potassium carbonate; In methanol; at 65℃; for 3h; General procedure: A dry flask was charged with the nitrogen containing heterocycles (1 mmol), aryl boronic acids (2.2 mmol), potassium carbonate (2 mmol) andCuMeSal (0.015 mmol)then anhydrous methanol (10 ml) was added. The reaction mixture was stirred at 65 oC, open to air, for 3 h (5 h in case of indole and benzimidazole), cooled to room temperature, filtered, and the precipitate was washed with methanol (2 ml), the filtrate was concentrated under vacuum, then stirred with ice water (30 ml) and extracted with ethyl acetate (3 × 50 ml), dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by chromatography or recrystallization as indicated with each compound.
  • 41
  • [ 288-32-4 ]
  • [ 577-19-5 ]
  • [ 98-95-3 ]
  • [ 23309-16-2 ]
YieldReaction ConditionsOperation in experiment
With [Cu2(1,4-benzenedicarboxylate)2(1,4-diazabicyclo[2.2.2]octane)]n; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 6h;Green chemistry; General procedure: The Cu2(BDC)2(DABCO) was used as a catalyst for the N-arylation of 4'-iodoacetophenone and imidazole. A mixture of 4'-iodoacetophenone (0.246 g, 1 mmol) and n-hexadecane (0.1 ml, 0.88 mmol) as an internal standard in DMF (4 ml) was added into a 25 mL flask containing the Cu2(BDC)2(DABCO) catalyst and KOtBu (0.224 g, 2 mmol) as a base. The catalyst concentration was calculated with respect to the copper/4'-iodoacetophenone molar ratio. Imidazole (0.204 g, 3 mmol) was then added, and the resulting mixture was stirred at 120 C for 3 h. Reaction conversion was monitored by withdrawing aliquots from the reaction mixture at different time intervals, quenching with aqueous NaOH solution (1 % w/w, 1 ml). The organic components were then extracted into diethyl ether (2 ml), dried over anhydrous Na2SO4, analyzed by GC with reference to n-hexadecane. The product identity was further confirmed by GC-MS. To investigate the recyclability of Cu2(BDC)2(DABCO), the catalyst was separated from the reaction mixture by simple centrifugation, washed with copious amounts of DMF, dried under air at room temperature for 1 h, and reused if necessary. For the leaching test, a catalytic reaction was stopped after 30 min, analyzed by GC, and centrifuged to remove the solid catalyst. The reaction solution was then stirred for a further 150 min. Reaction progress, if any, was monitored by GC as previously described. For homogeneity test, Cu(NO3)2*3H2O (5 mol %), H2BDC (5 mol %), and DABCO (5 mol %) were used as catalytic mixture for the reaction. After 30 min of reaction time, the reaction mixture was centrifuged and the mother liquor was further stirred for a further 150 min under control of GC. Furthermore, copper content of the mother liquor was confirmed by ICP analysis.
  • 42
  • diphenyliodonium tetrafluoroborate [ No CAS ]
  • [ 23309-16-2 ]
  • C15H12N3O2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With air; heterogeneous copper Schiff-base modified SBA-15 catalyst; In N,N-dimethyl-formamide; at 80℃; for 6h;Catalytic behavior; At first diphenyliodonium tetrafluoroborate was synthesizedaccording to procedure reported previously [31] and characterizedby1H and13C NMR and mass spectral analysis (see Supplementarycontent). A mixture of N-heteroarene (1.0 mmol), diphenyliodo-nium salt (1.5 mmol), catalyst and DMF (3 mL) was stirred at 80Cfor a desired time in air. After cooled down to room tempera-ture, heterogeneous catalyst was separated out by centrifugation.The liquid part was then subjected to rotary evaporation andthe residue obtained was passed through a silica gel column(dichloromethane/acetone = 5:1-2:1 v/v) to afford the desired ary-lazolium salt. The product was analyzed by1H and13C NMR andmass spectroscopy.
  • 43
  • [ 23309-16-2 ]
  • 1-(2-azidophenyl)-3-benzylimidazolium chloride [ No CAS ]
  • 44
  • [ 23309-16-2 ]
  • 1-(2-azidophenyl)-3-(2-picolyl)imidazolium chloride [ No CAS ]
  • 45
  • [ 23309-16-2 ]
  • 1-(2-azidophenyl)-3-ethylimidazolium bromide [ No CAS ]
  • 46
  • [ 23309-16-2 ]
  • 1-(2-azidophenyl)-3-octylimidazolium bromide [ No CAS ]
  • 47
  • [ 23309-16-2 ]
  • 1-(2-benzyl)-benzo[d]imidazo[1,2-a]imidazole [ No CAS ]
  • 48
  • [ 23309-16-2 ]
  • 1-(2-picolyl)-benzo[d]imidazo[1,2-a]imidazole [ No CAS ]
  • 49
  • [ 23309-16-2 ]
  • 1-(2-ethyl)-benzo[d]imidazo[1,2-a]imidazole [ No CAS ]
  • 50
  • [ 23309-16-2 ]
  • C17H23N3 [ No CAS ]
  • 51
  • [ 23309-16-2 ]
  • (1-(2-azidophenyl)-3-benzyl-1H-imidazol-2(3H)-ylidene)silver(I) chloride [ No CAS ]
  • 52
  • [ 23309-16-2 ]
  • [ 133307-45-6 ]
  • 53
  • [ 23309-16-2 ]
  • [ 191349-69-6 ]
  • 54
  • [ 23309-16-2 ]
  • [ 68008-91-3 ]
  • 55
  • [ 23309-16-2 ]
  • [ 68008-93-5 ]
  • 56
  • [ 23309-16-2 ]
  • N-ethyl-4-(imidazo[1,2-a]quinoxalin-4-yl)aniline [ No CAS ]
  • 57
  • [ 23309-16-2 ]
  • [ 68030-24-0 ]
  • 58
  • [ 23309-16-2 ]
  • 2-(1H-imidazol-1-yl)-N-methylaniline [ No CAS ]
  • 60
  • 2-aminophenyl N,N-diethylcarbamate [ No CAS ]
  • [ 288-32-4 ]
  • [ 23309-16-2 ]
  • 61
  • [ 288-32-4 ]
  • [ 1141-13-5 ]
  • [ 23309-16-2 ]
  • 62
  • [ 288-32-4 ]
  • [ 528-29-0 ]
  • [ 23309-16-2 ]
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