19235-88-2|4-Nitro-2-pyridinecarbonitrile| Ambeed

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Structure of 19235-88-2

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Quality Control of [ 19235-88-2 ] Purity: 98% SDS Specification

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Product Details of [ 19235-88-2 ]

CAS No. :	19235-88-2
Formula :	C₆H₃N₃O₂
M.W :	149.11
SMILES Code :	N#CC1=NC=CC([N+]([O-])=O)=C1
MDL No. :	MFCD00191627
InChI Key :	ONDDYTHSSNTDLR-UHFFFAOYSA-N
Pubchem ID :	568650

Safety of [ 19235-88-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H315-H318-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P310-P321-P330-P332+P313-P362-P403+P233-P405-P501
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 19235-88-2 ]

* 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 [ 19235-88-2 ]

[ 19235-88-2 ] Synthesis Path-Downstream 1~45

1
[ 19235-88-2 ]
[ 62020-02-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With chloro-trimethyl-silane; water; at 20℃; for 1h;	4-Nitropicolinonitrile (100 mg, 0.67 mmol), chlorotrimethylsilane (0.17 mL, 1.4 mmol) and H2O (0.024 mL, 1.4 mmol) was sonicated in a sonicator at rt for 1.0 h. It was diluted with EtOAc, washed with NaHCO3, brine and dried over Na2SO4. After removal of solvent, 99A (134 mg, 100% yield) was obtained as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 8.29 (dd, J=5.27, 2.20 Hz, 1H) 8.74 (d, J=2.20 Hz, 1H) 8.98 (d, J=5.27 Hz, 1H).

References: [1]Patent: US2010/227894,2010,A1 .Location in patent: Page/Page column 76.
[2]ACS Catalysis,2015,vol. 5,p. 20 - 26.
[3]Synthetic Communications,1993,vol. 23,p. 3149 - 3155.
[4]Chemistry - A European Journal,2011,vol. 17,p. 11428 - 11431.

2
[ 151-50-8 ]
C₆H₇N₂O₃⁽¹⁺⁾*CH₃O₄S^(1-) [ No CAS ]
[ 19235-88-2 ]

References: [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174.

3
[ 19235-88-2 ]
[ 13509-19-8 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With sodium sulfite; In ice-water; sulfuric acid; water;	III-2-2: Synthesis of 4-nitropicolinic acid A solution of 5.00 g (34 mmol) of 2-cyano-4-nitropyridine dissolved in 50 g of 90% sulfuric acid was stirred at 120 C. for 2 hours. Then, at 20 to 25 C., a solution of 5.60 g of sodium sulfite in 10 ml of water was dropwise added, and the mixture was stirred at the same temperature for one hour, and further, at 80 C. for one hour under heating. After cooling, 100 g of ice-water was added, and the mixture was adjusted to a pH of about 2 with sodium carbonate. The mixture was left to stand in a refrigerator, resulting in precipitation of the solid. The solid was collected by filtration and recrystallized from a water-acetone mixture to obtain 3.50 g of pale yellow crystals (yield 62.1%). m.p.: 157-158 C. (decompd.). IR (KBr): 1710, 1600, 1585, 1535 cm-1.

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 19366 - 19369.
[2]Patent: US5219847,1993,A .
[3]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174.

5
[ 19235-88-2 ]
4-fluoro-2-pyridinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 0.583333h;	4-nitropicolinonitrile B.39 (5 g, 33.5 mmol) in 64 mL DMF was stirred at room temperature as 67 mL TBAF (1 M in THF, 67 mmol) was added. After 35 minutes, the reaction was poured into 500 mL 1 : 1 ethyl acetate-water. The organic layer was washed with water and brine, dried over Na2SO4 and condensed. The orange-brown residue was purified by flash chromatography (0-10-100% ethyl acetate in hexane) to give 4-fluoropicolinonitrile B.40 (2.78 g, 68%). IH NMR (500 MHz, CHLOROFORM-d) δ ppm 8.72 (1 H, dd, J=7.9, 5.7 Hz), 7.48 (1 H, dd, J=8.1, 2.4 Hz), 7.30 (1 H, ddd, J=8.1, 5.6, 2.4 Hz).

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1906 - 1909.
[2]Organic Letters,2005,vol. 7,p. 577 - 579.
[3]Patent: WO2009/158011,2009,A1 .Location in patent: Page/Page column 174.

6
[ 694-59-7 ]
[ 19235-88-2 ]

References: [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174.

7
[ 1124-33-0 ]
[ 19235-88-2 ]

References: [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174.
[2]Journal of Organometallic Chemistry,2021,vol. 954-955.

8
[ 19235-88-2 ]
[ 29082-91-5 ]

References: [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174.
[2]Journal of the American Chemical Society,2012,vol. 134,p. 19366 - 19369.

9
[ 1124-33-0 ]
[ 77-78-1 ]
[ 19235-88-2 ]

Yield	Reaction Conditions	Operation in experiment
23.0%	In water;	III-2-1: Synthesis of 2-cyano-4-nitropyridine A mixture of 20.0 g (0.14 mol) of 4-nitropyridine N-oxide and 18.0 g (0.14 mol) of dimethylsulfuric acid was stirred at 65 to 70 C. for 2 hours, and then left to stand in a refrigerator overnight, whereby solidification occurred. The solid was dissolved in 50 ml of water, and a solution of 14.6 g (0.3 mol) of sodium cyanide in 100 ml of water was dropwise added with vigorous stirring under a nitrogen atmosphere at -7 to -8 C., followed by stirring at the same temperature for 7 hours. After standing at room temperature overnight, the precipitates were collected by filtration, washed with water, dried and recrystallized from isopropyl ether to give 4.90 g of yellow crystals (yield 23.0%). m.p.: 70.0-71.0 C. IR (KBr): 2240, 1600, 1575 cm-1.

References: [1]Patent: US5219847,1993,A .

10
silver perchlorate [ No CAS ]
[ 19235-88-2 ]
[ 19989-90-3 ]

References: [1]Journal of Inorganic and Nuclear Chemistry,1968,vol. 30,p. 651 - 656.
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ag: MVol.B6, 1.5.1.10, page 99 - 102.

11
silver perchlorate [ No CAS ]
[ 19235-88-2 ]
Ag(2-cyano-4-nitro-pyridine)2ClO₄ [ No CAS ]

References: [1]Journal of Inorganic and Nuclear Chemistry,1968,vol. 30,p. 651 - 656.
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ag: MVol.B6, 1.5.1.10, page 99 - 102.

12
[ 111-29-5 ]
[ 19235-88-2 ]
[ 1179953-84-4 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4657 - 4667.

13
[ 19235-88-2 ]
[ 19989-90-3 ]

References: [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ag: MVol.B6, 1.5.1.10, page 99 - 102.

14
[ 1355592-27-6 ]
[ 19235-88-2 ]
[ 1355593-41-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With caesium carbonate; In 1,4-dioxane; at 100℃; for 24h;Sealed tube;	Step 1: methyl 6-[(2-cyanopyridin-4-yl)oxy]-5,6,7,8-tetrahydronaphthalene-2-carboxylate Intermediate 90A mixture of methyl 6-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate (0.100 g, 0.48 mmol), 4-nitro-2-pyridinecarbonitrile (0.144 g, 0.969 mmol), cesium carbonate (0.473 g, 1.45 mmol) and 1,4-dioxane (2.00 mL) was heated in a sealed tube at 100 C. for 24 h. Water was added and the mixture was extracted into EtOAc (2×). The organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by silica gel chromatography (0% to 50% EtOAc/hexane) to afford the title compound (142 mg, 95%). LCMS (FA) ES+ 309.

References: [1]Patent: US2012/15943,2012,A1 .Location in patent: Page/Page column 78.

15
[ 75-89-8 ]
[ 19235-88-2 ]
[ 1156542-38-9 ]

Yield	Reaction Conditions	Operation in experiment
> 99%		To a solution of potassium tert-butoxide (0.45 g, 4.02 mmol) in tetrahydrofuran (8 mL) is added 2,2,2-trifluoroethanol (0.27 mL, 3.69 mmol), and the mixture is stirred at room temperature for 20 minitues. A solution of 4-nitropicolinonitrile (0.50 g, 3.35 mmol) in tetrahydrofuran (8 mL) is added dropwise the mixture, and the resulting mixture is stirred at room temperature for 20 minitues. The reaction mixture is poured into saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (30 mL). The organic layer is dried over sodium sulfate and concentrated in vacuo to give 0.71 g (>99% yield) of the title compound as yellow oil. This material is used for the next reaction (Step-2) without further purification.MS (ESI) m/z: 203 (M+H)+.

References: [1]Patent: WO2012/53186,2012,A1 .Location in patent: Page/Page column 108-109.

16
[ 19235-88-2 ]
[ 1414851-44-7 ]