100367-55-3

Basic information

• Product Name: 2-Cyano-5-nitropyridine
• Synonyms: 2-PYRIDINECARBONITRILE, 5-NITRO-;2-CYANO-5-NITROPYRIDINE;6-CYANO-3-NITROPYRIDINE;5-nitropyridine-2-carbonitrile;2-Pyridinecarbonitrile,5-nitro-(9CI);5-NITROPYRIDINE-2-CARBONITRILE,PURITY:95% MIN(HPLC);5-Nitropicolinonitrile;5-Nitro-2-pyridinecarbonitrile
• CAS NO: 100367-55-3
• Molecular Formula: C₆H₃N₃O₂
• Molecular Weight: 149.11
• EINECS: 1312995-182-4
• Product Categories: PYRIDINE;Aromatics Compounds;Aromatics;Bases & Related Reagents;Nucleotides;Pyridines
• Mol File: 100367-55-3.mol

Chemical Properties

• Melting Point: 43 °C
• Boiling Point: 344.557 °C at 760 mmHg
• Flash Point: 162.183 °C
• Appearance: Green solid
• Density: 1.418 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Ethyl Acetate, Methanol
• PKA: -4.35±0.10(Predicted)
• CAS DataBase Reference: 2-Cyano-5-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyano-5-nitropyridine(100367-55-3)
• EPA Substance Registry System: 2-Cyano-5-nitropyridine(100367-55-3)

Safety Data

• Hazardous Substances Data: 100367-55-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Cyano-5-nitropyridine is used as a synthetic intermediate for the production of various chemical compounds. Its unique structure allows it to be a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The presence of both nitro and cyano functional groups makes it a versatile starting material for further chemical reactions and modifications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Cyano-5-nitropyridine is used as a key intermediate in the synthesis of various drug candidates. Its ability to be modified and functionalized makes it an essential component in the development of new medications with potential therapeutic applications.
Used in Agrochemical Industry:
2-Cyano-5-nitropyridine also finds application in the agrochemical industry, where it is used as a synthetic intermediate for the development of new pesticides and other crop protection agents. Its structural diversity and reactivity contribute to the creation of innovative and effective products for agricultural use.

InChI:InChI=1/C6H3N3O2/c7-3-5-1-2-6(4-8-5)9(10)11/h1-2,4H

Upstream product

• 59290-34-5 5-nitropyridine-2-carboxamide 
• 4487-59-6 2-bromo-5-nitropyridine 
• 544-92-3 copper(I) cyanide 
• 100-70-9 2-Cyanopyridine 
• 143-33-9 sodium cyanide 
• 5418-51-9 5-nitro-2-hydroxypyridine 
• 773837-37-9 sodium cyanide 
• 4214-76-0 5-nitro-pyridin-2-ylamine 

Downstream Products

• 55338-73-3 5-amino-2-cyanopyridine 
• 15069-92-8 5-hydroxypicolinic acid 
• 24242-20-4 5-amino-pyridine-2-carboxylic acid 
• 30766-11-1 5-bromoisonicotinic acid 
• 32046-43-8 5-Iodpicolinsaeure 
• 29082-92-6 5-methoxypyridine-2-carboxylic acid 
• 86873-62-3 5-Acetylaminopyridin-2-carbonsaeure 
• 86873-61-2 5-Hydroxylaminopyridin-2-carbonsaeure 
• 1011244-92-0 5-nitro-N-(4-trifluoromethylphenyl)-2-pyridinecarboxamide 
• 1293979-18-6 C₁₃H₇F₂N₃O 
• 51460-32-3 1-(5-aminopyridin-2-yl)ethan-1-one 
• 1011244-74-8 C₁₃H₁₀F₃N₃O 

Relevant articles and documents

The Synthesis of the High-Potency Sweetener, NC-00637. Part 2: Preparation of the Pyridine Moiety

The pyridine moiety within the high-potency sweetener, NC-00637 (1), 5-amino-2-cyanopyridine (4), was prepared from 2-hydroxy-5-nitropyridine (10). The sequence involved the conversion of the hydroxy group to bromide followed by substitution with cyanide to give 2-cyano-5-nitropyridine (8). Reduction of the nitro group proved to be troublesome when catalytic hydrogenation was used. Iron with an acid gave a reproducible reaction that could be used at scale.

Preparation of novel heteroisoindoles from nitropyridines and nitropyridones

The reaction of nitropyridine derivatives with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5.4.0]undecene proceeded tandem cyclization to give polycyclic pyrrolopyridines or imidazopyridines. On the other hand, N-protected 3-nitro- and 5-nitropyridones and N,N-diprotected 5-nitrouracil gave corresponding bicyclic pyrroles in good yields under the similar conditions.

Preparation method of 2-nitrile-5-hydroxypyridine

The invention relates to a preparation method of 2-nitrile-5-hydroxypyridine. The method comprises the steps: taking 2-bromine-5-nitropyridine, NaCN, CuCN, dimethylformamide, KH2PO4 and the like as starting raw materials to generate 2-nitrile-5-nitropyridine, adding ethyl acetate, an appropriate amount of reduced Fe powder and an enough amount of acetic acid, adding an appropriate amount of H2SO4 solution and NaNO2, and performing filtering and drying to obtain orange-yellow solid 2-nitrile-5-hydroxypyridine. The method is mild in reaction condition and low in cost; the raw materials are easy to obtain; and the method is suitable for mass production of a plant.

QUINOLINE COMPOUNDS AS MODULATORS OF RAGE ACTIVITY AND USES THEREOF

Quinoline compounds are disclosed that have a formula represented by the following: and wherein Cy, R1, R4a, R4b, and n are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diabetes complications, inflammation, and neurodegeneration, obesity, cancer, ischemia/reperfusion injury, cardiovascular disease and other diseases related to RAGE activity.

NOVEL AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION

The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5, W and X are as described herein, compositions including the compounds and methods of using the compounds.

COMPOUND HAVING BENZAMIDE SKELETON AND CYCLOOXYGENASE (COX-1)-SELECTIVE INHIBITORY ACTIVITY

This invention provides a novel COX-1-selective inhibitor. This invention relates to a novel compound represented by the formula below or a salt thereof. This invention also relates to an analgesic agent, an antiinflammatory agent, an antitumor agent, an antiplatelet aggregation agent, and a cyclooxygenase-1-selective inhibitor comprising, as an active ingredient, such compound or salt thereof.

Discovery of inhibitors of aberrant gene transcription from libraries ofdna binding molecules: Inhibition of LEF-1-mediated gene transcription and oncogenic transformation

The screening of a >9000 compound library of synthetic DNA binding molecules for selective binding to the consensus sequence of the transcription factor LEF-1 followed by assessment of the candidate compounds in a series of assays that characterized functional activity (disruption of DNA-LEF-1 binding) at the intended target and site (inhibition of intracellular LEF-1-mediated gene transcription) resulting in a desired phenotypic cellular change (inhibit LEF-1-driven cell transformation) provided two lead compounds: lefmycin-1 and lefmycin-2. The sequence of screens defining the approach assures that activity in the final functional assay may be directly related to the inhibition of gene transcription and DNA binding properties of the identified molecules. Central to the implementation of this generalized approach to the discovery of DNA binding small molecule inhibitors of gene transcription was (1) the use of a technically nondemanding fluorescent intercalator displacement (FID) assay for initial assessment of the DNA binding affinity and selectivity of a library of compounds for any sequence of interest, and (2) the technology usedto prepare a sufficiently large library of DNA binding compounds.

Cyclooxygenase-1-selective inhibitors are attractive candidates for analgesics that do not cause gastric damage. Design and in vitro/in vivo evaluation of a benzamide-type cyclooxygenase-1 selective inhibitor

Although cyclooxygenase-1 (COX-1) inhibition is thought to be a major mechanism of gastric damage by nonsteroidal anti-inflammatory drugs (NSAIDs), some COX-1-selective inhibitors exhibit strong analgesic effects without causing gastric damage. However, it is not clear whether their analgesic effects are attributable to COX-1-inhibitory activity or other bioactivities. Here, we report that N-(5-amino-2-pyridinyl)-4-(trifluoromethyl)benzamide (18f, TFAP), which has a structure clearly different from those of currently available COX-1-selective inhibitors, is a potent COX-1-selective inhibitor (COX-1 IC 50 = 0.80 ± 0.05 μM, COX-2 IC50 = 210 ± 10 μM). This compound causes little gastric damage in rats even at an oral dose of 300 mg/kg, though it has an analgesic effect at as low a dose as 10 mg/kg. Our results show that COX-1-selective inhibitors can be analgesic agents without causing gastric damage.

Compounds and compositions as anticoagulants

The present invention relates to novel biheterocyclic derivatives which are factor Xa inhibitors; the pharmaceutically acceptable salts and N-oxides thereof; their uses as therapeutic agents and the methods of their making.

Novel potassium channel openers: Synthesis and pharmacological evaluation of new N-(substituted-3-pyridyl)-N'-alkylthioureas and related compounds

This report describes the synthesis and pharmacological evaluation of a series of novel potassium channel openers related to the pinacidil-type compounds. Thioureas, cyanoguanidines, and pyridine N-oxides were systematically evaluated for their effects on both the inhibition of spontaneous mechanical activity in rat portal vein (in vitro) and their antihypertensive activity (in vivo), and the structure-activity relationship for this series of compounds was discussed. Good correlation between in vitro and iv antihypertensive activity was observed for these compounds. Among them, cyanoguanidines bearing a conformationally rigid unit such as a norbornyl group generally possessed potent activity in both in vitro and in vivo studies. Especially, N-(6-amino-3-pyridyl)-N'-cyano-N''-(1-methyl-2- norbornyl)guanidine (23d) was identified as a more potent potassium channel opener in vitro (EC100 = 3 x 10-8 M) than pinacidil (EC100 = 10-7 M).