6219-55-2|1-(4-Nitrophenyl)-1H-1,2,4-triazole| Ambeed

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Quality Control of [ 6219-55-2 ] Purity: 95+% SDS Specification

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Product Details of [ 6219-55-2 ]

CAS No. :	6219-55-2
Formula :	C₈H₆N₄O₂
M.W :	190.16
SMILES Code :	O=[N+](C1=CC=C(N2N=CN=C2)C=C1)[O-]
MDL No. :	MFCD09473439
InChI Key :	YGFKLGQEQNGWOB-UHFFFAOYSA-N
Pubchem ID :	11095398

Safety of [ 6219-55-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
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

Application In Synthesis of [ 6219-55-2 ]

* 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 [ 6219-55-2 ]

[ 6219-55-2 ] Synthesis Path-Downstream 1~35

1
[ 288-88-0 ]
[ 350-46-9 ]
[ 6219-55-2 ]

Yield	Reaction Conditions	Operation in experiment
91%		At 0 C., to a solution of 1,2,4-triazole (2.7 g, 39.01 mmol) in DMF (50 mL) was added sodium hydride (1.6 g, 39.01 mmol). The mixture was stirred for 30 minutes and 1-flouro-4-nitrobenzene (5.0 g, 35.46 mmol) was added, and the resultant mixture was stirred for further 2 hours. Water (150 mL) was added slowly to the mixture, there was solid precipitated. After filtration, the filter cake was washed with water (50 mL×3), and the solid was dried in vacuum for 8 hours to give yellow solid 10-b (6.2 g, yield: 91%), which was used for the next step without further purification. LC-MS (ESI): m/z=191 [M+H]+
		45A 1-(4-Nitro-phenyl)-1H-[1,2,4]triazole 15 g of 1,2,4 triazole were dissolved in DMF and 8.8 g of NaH (60% in oil) were added. The mixture was stirred at RT for 6 hours and 28.2 g of 1 fluoro-4-nitrobenzene were added. After 6 hours at RT, water was added and the resulting precipitate was washed by ethanol to give 36 g of a product melting at 198 C. used as such in the next step.
		[0004981 To a stirred solution of compound 1 (3 g, 1 eq) in DMF (40 mL), K2C03 (8.8 g, 3 eq) was added and stirred for 15 mm followed by the addition of compound 2 (3.6 g, 1 eq). The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with ice cold water. The precipitated solid was collected by filtration, washed with water and dried under reduced pressure to afford the title compound 3. LCMS (mlz): 191.00 (M + 1).

120 mg

With potassium carbonate; In dimethyl sulfoxide; at 20 - 80℃; for 16.25h;

1(200 mg, 1.41 mmol), DMSO (3 mL), 1,2,4-triazole (1.1 eq), K2C03 (3.0 eq), RT for5 mm; gradually heated to 80C for 10 mm and stirred for 16 h. Work up and column purification afforded 120 mg of 2.

References: [1]Patent: US2015/336982,2015,A1 .Location in patent: Paragraph 0160; 0161.
[2]Australian Journal of Chemistry,1993,vol. 46,p. 417 - 425.
[3]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1935 - 1946.
[4]Journal of Medicinal Chemistry,1999,vol. 42,p. 4981 - 5001.
[5]Patent: US2005/143384,2005,A1 .Location in patent: Page/Page column 23.
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2012,vol. 51,p. 731 - 738.
[7]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000498.
[8]Patent: WO2016/73652,2016,A1 .Location in patent: Page/Page column 61.

2
[ 288-88-0 ]
[ 350-46-9 ]
[ 6219-55-2 ]
[ 16759-47-0 ]

References: [1]Synthetic Communications,1993,vol. 23,p. 1947 - 1952.

3
[ 6219-55-2 ]
4,4'-bis(1'',2'',4''-triazol-1''-yl)azoxybenzene [ No CAS ]
[ 100-29-8 ]

References: [1]Australian Journal of Chemistry,1993,vol. 46,p. 417 - 425.

4
[ 41253-21-8 ]
[ 350-46-9 ]
[ 6219-55-2 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1799 - 1810.
[2]Journal of Organic Chemistry,2011,vol. 76,p. 3286 - 3295.

5
[ 6219-55-2 ]
4-[1,2,4]Triazol-1-yl-phenylamine; hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1799 - 1810.

6
[ 6219-55-2 ]
[ 6523-49-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With ammonium chloride; zinc; In ethanol; water; for 0.5h;Reflux;	Compound 10-b (3.0 g, 15.78 mmol) and ammonium chloride (2.1 g, 39.62 mmol) were dissolved in 50% ethanol-water (60 mL). Zn-powder (2.6 g, 40 mmol) was then added. The mixture was refluxed for 30 minutes. After cooled to room temperature, the mixture was filtrated, and the filter cake was washed with ethanol (10 mL). The combined filtrate were concentrated under reduced pressure, and the residue was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give yellow solid 10-a (1.1 g, yield: 81%), which was used directly for the next step without purification. LC-MS (ESI): m/z=161 [M+H]+.
		45B: 4-[1,2,4]Triazol-1-yl-phenylamine 18 g of Intermediate 45A was dissolved in 300 ml of ethanol and 70 g of tin dichloride was added. The mixture was refluxed for 4 hours, ethanol was evaporated and dilute sodium hydroxide was added. After extraction with dichloromethane, the dichloromethane phase was dried over magnesium sulfate and evaporated. A powder was obtained, which was washed with pentane to give 12 g of a white solid. 1H NMR (DMSO-d6): 9.00 (1H,s), 8.08 (1H,s), 7.44 (2H, d), 6.69 (2H,d), 5.55 (2H, broad signal).
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h;	[000499j To a stirred solution ofcompound3 (1.8 g, 1 eq) in methanol (10 mL), 10%Pd-C (0.5 g) was added and stirred under hydrogen atmosphere (balloon pressure) at room temperature for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was evaporated under reduced pressure to afford the title compound 4. LCMS (mlz): 161.00 (M + 1).

1.2 g

With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 16h;

2 (1.5 g, 8.42 mmol), MeOH (30 mL), Pd/C (1.0 g), RT, H2 (balloon pressure), 16 h. Work up and column purification afforded 1.2 g of 3,

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1935 - 1946.
[2]Patent: US2015/336982,2015,A1 .Location in patent: Paragraph 0160; 0162.
[3]Applied Spectroscopy,1995,vol. 49,p. 1111 - 1119.
[4]Patent: US2005/143384,2005,A1 .Location in patent: Page/Page column 23-24.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2012,vol. 51,p. 731 - 738.
[6]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000499.
[7]Patent: WO2016/73652,2016,A1 .Location in patent: Page/Page column 61.

Yield	Reaction Conditions	Operation in experiment
		1. 4-(1,2,4-Triazol-1-yl)nitrobenzene 1,2,4-Triazole sodium derivative (90%) (17.74 g, 0.18 mol) and 1-fiuoro-4-nitrobenzene (25 g, 0.18 mol), in DMF, (150 ml) was stirred at room temperature for 4 days. Water (300 ml) and ethyl acetate (500 ml) were added and the mixture extracted. The organic layer was separated, washed with water (3*300 ml), dried (MgSO4) and evaporated to give the desired product (24.8 g); δ (360 MHz, CDCl3)7.92 (2H, d, J=9.1 Hz, Ar--H), 8.17 (1H, s, Ar--H), 8.40 (2H, d, J=9.1 Hz, Ar--H), 8.48 (1H, s, Ar--H).

9
[ 6219-55-2 ]
4-[1,2,4]triazol-1-yl-phenylamine; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4981 - 5001.

10
[ 6219-55-2 ]
[ 27199-87-7 ]