23309-16-2|1-(2-Nitrophenyl)-1H-imidazole| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 23309-16-2 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 23309-16-2 ]

CAS No. :	23309-16-2
Formula :	C₉H₇N₃O₂
M.W :	189.17
SMILES Code :	O=[N+](C1=CC=CC=C1N2C=CN=C2)[O-]
MDL No. :	MFCD01795851
InChI Key :	HESJLLCGKVDGIB-UHFFFAOYSA-N
Pubchem ID :	821062

Safety of [ 23309-16-2 ]

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

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 1~35

1
[ 288-32-4 ]
[ 1493-27-2 ]
[ 23309-16-2 ]

Yield	Reaction Conditions	Operation 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

References: [1]Tetrahedron Letters,2007,vol. 48,p. 4207 - 4210.
[2]ChemSusChem,2013,vol. 6,p. 1737 - 1744.
[3]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6601 - 6610.
[4]Synthetic Communications,2008,vol. 38,p. 626 - 636.
[5]Journal of the Chemical Society. Perkin transactions I,1997,p. 1605 - 1608.
[6]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1938 - 1942.
[7]European Journal of Organic Chemistry,2011,p. 6998 - 7010.
[8]Chemical Communications,2017,vol. 53,p. 2402 - 2405.
[9]Tetrahedron Letters,2020,vol. 61.
[10]Journal of Medicinal Chemistry,1991,vol. 34,p. 2671 - 2677.
[11]Australian Journal of Chemistry,1993,vol. 46,p. 417 - 425.
[12]Patent: US6235740,2001,B1 .
[13]Organic Letters,2012,vol. 14,p. 452 - 455.
[14]Tetrahedron Letters,2013,vol. 54,p. 5984 - 5990.
[15]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 3031 - 3037.
[16]Organic and biomolecular chemistry,2020,vol. 18,p. 1612 - 1622.

2
[ 23309-16-2 ]
[ 26286-54-4 ]

Yield	Reaction Conditions	Operation 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

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1605 - 1608.
[2]ChemSusChem,2013,vol. 6,p. 1737 - 1744.
[3]Chemical Communications,2017,vol. 53,p. 2402 - 2405.
[4]European Journal of Organic Chemistry,2011,p. 6998 - 7010.
[5]Journal of Medicinal Chemistry,2019,vol. 62,p. 3924 - 3939.
[6]Journal of Medicinal Chemistry,1991,vol. 34,p. 2671 - 2677.
[7]Organic Letters,2012,vol. 14,p. 452 - 455.
[8]Tetrahedron Letters,2013,vol. 54,p. 5984 - 5990.
[9]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 3031 - 3037.
[10]ChemMedChem,2019,vol. 14,p. 1031 - 1040.
[11]Journal of Medicinal Chemistry,2019.
[12]Organic and biomolecular chemistry,2020,vol. 18,p. 1612 - 1622.

4
[ 288-32-4 ]
[ 88-73-3 ]
[ 23309-16-2 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 7951 - 7954.
[2]RSC Advances,2015,vol. 5,p. 92121 - 92127.
[3]Tetrahedron,2008,vol. 64,p. 2471 - 2479.
[4]Synthesis,2009,p. 2517 - 2522.
[5]Synthetic Communications,2008,vol. 38,p. 626 - 636.
[6]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 515 - 517.
[7]Journal of the American Chemical Society,2005,vol. 127,p. 9948 - 9949.
[8]Synthetic Communications,2012,vol. 42,p. 114 - 121.
[9]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1938 - 1942.
[10]RSC Advances,2014,vol. 4,p. 7321 - 7329.
[11]New Journal of Chemistry,2016,vol. 40,p. 1454 - 1459.
[12]Cuihua Xuebao/Chinese Journal of Catalysis,2014,vol. 35,p. 1818 - 1824.
[13]Chinese Journal of Chemistry,2012,vol. 30,p. 2389 - 2393,5.
[14]ChemMedChem,2019,vol. 14,p. 1031 - 1040.

5
[ 23309-16-2 ]
[ 247-79-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1605 - 1608.

6
[ 23309-16-2 ]
[ 192927-28-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1605 - 1608.
[2]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 3031 - 3037.
[3]Chemical Communications,2017,vol. 53,p. 2402 - 2405.

7
[ 23309-16-2 ]
[ 1043391-18-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6601 - 6610.

8
[ 288-32-4 ]
[ 577-19-5 ]
[ 23309-16-2 ]

Yield	Reaction Conditions	Operation 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).

References: [1]Applied Catalysis A: General,2016,vol. 513,p. 53 - 66.
[2]European Journal of Organic Chemistry,2011,p. 3353 - 3360.
[3]Letters in Organic Chemistry,2011,vol. 8,p. 325 - 331.
[4]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 515 - 517.
[5]Tetrahedron Letters,2014,vol. 55,p. 3049 - 3051.
[6]Applied Organometallic Chemistry,2017,vol. 31.
[7]Polyhedron,2013,vol. 51,p. 132 - 141.

9
[ 288-32-4 ]
2-NO₂-C₆H₄-X; X = I, Br [ No CAS ]
[ 23309-16-2 ]

References: [1]Synthesis,2009,p. 2517 - 2522.

10
[ 288-32-4 ]
[ 609-73-4 ]
[ 23309-16-2 ]

Yield	Reaction Conditions	Operation 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).

References: [1]European Journal of Organic Chemistry,2010,p. 3621 - 3630.
[2]Tetrahedron,2014,vol. 70,p. 6082 - 6087.
[3]Journal of Organic Chemistry,2011,vol. 76,p. 3151 - 3159.
[4]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1234 - 1239.
[5]Journal of Medicinal Chemistry,2019.
[6]Journal of Medicinal Chemistry,2019,vol. 62,p. 3924 - 3939.

11
[ 23309-16-2 ]
[ 1352820-79-1 ]