18699-87-1

Basic information

• Product Name: 2-Methyl-3-nitropyridine
• Synonyms: 3-NITRO-2-PICOLINE;3-NITRO-2-METHYLPYRIDINE;2-METHYL-3-NITROPYRIDINE;Pyridine, 2-methyl-3-nitro- (9CI);3-Nitro-2-methylpyridine 3-Nitro-2-picoline;2-METHYL-3-NITROPYRIDINE 95%;3-NITROPICOLINE;2-Methyl-3-nitropyri
• CAS NO: 18699-87-1
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12
• EINECS: -0
• Product Categories: NITRO;Pyridine;Pyridines
• Mol File: 18699-87-1.mol

Chemical Properties

• Melting Point: 32-33°
• Boiling Point: 86°C/5mmHg(lit.)
• Flash Point: 83.1 °C
• Appearance: beige moist crystals
• Density: 1.246 g/cm³
• Vapor Pressure: 0.235mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• PKA: 1.92±0.10(Predicted)
• CAS DataBase Reference: 2-Methyl-3-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-nitropyridine(18699-87-1)
• EPA Substance Registry System: 2-Methyl-3-nitropyridine(18699-87-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 18699-87-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-3-nitropyridine is used as a starting reagent for the synthesis of 3-substituted-4 or 6-azaindoles, which are important heterocyclic compounds with potential applications in medicinal chemistry. These azaindole derivatives have been found to possess a range of biological activities, making them valuable for the development of new drugs.
Used in Organic Synthesis:
2-Methyl-3-nitropyridine is also used as a reagent in the preparation of 3-azaindolyl-4-arylmalemides. These compounds have been reported to exhibit antiproliferative activity, which can be beneficial in the development of anticancer agents. The synthesis of such compounds can contribute to the discovery of novel therapeutic agents with improved efficacy and selectivity in targeting cancer cells.

Synthesis Reference(s)

Tetrahedron, 54, p. 6311, 1998 DOI: 10.1016/S0040-4020(98)00328-7Journal of Heterocyclic Chemistry, 29, p. 359, 1992 DOI: 10.1002/jhet.5570290213Synthetic Communications, 20, p. 2965, 1990 DOI: 10.1080/00397919008051513

InChI:InChI=1/C6H6N2O2/c1-5-6(8(9)10)3-2-4-7-5/h2-4H,1H3

Upstream product

• 637-53-6 thioacetanilide 
• 142-71-2 copper diacetate 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 659742-21-9 (6-methylpyridin-3-yl)boronic acid 
• 173417-34-0 dimethyl 2-(3-nitropyridin-2-yl)malonate 
• 2530-26-9 3-nitropyridine 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 108-48-5 2,6-dimethylpyridine 
• 15513-52-7 3-nitro-2,6-lutidine 
• 823-96-1 Trimethylboroxine 
• 68-12-2 N,N-dimethyl-formamide 
• 7664-93-9 sulfuric acid 
• 587-14-4 N,N'-diphenylsulfamide 

Downstream Products

• 65156-92-5 2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine 
• 3430-10-2 2-methyl-3-pyridinamine 
• 5236-76-0 2-methyl-3-nitropyridine 1-oxide 
• 10261-94-6 3-nitropyridine-2-carboxaldehyde 
• 65156-92-5 (E)-N,N-dimethyl-2-(3-nitropyridin-2-yl)ethenamine 
• 272-49-1 1H-pyrrolo[3,2-b]pyridine 
• 60917-52-4 2-phenyl-8-nitroindolizine 
• 60891-78-3 2-methyl-8-nitroindolizine 
• 1018950-15-6 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester 
• 1094619-88-1 (R)-6-(3-aminopyridin-2-yl)-5-(1-phenylpropan-2-yl)-3-(trifluoromethyl)isoxazolo[5,4-d]pyrimidin-4(5H)-one 
• 1094619-69-8 (R)-2,2,2-trifluoro-N-(2-(4-oxo-5-(1-phenylpropan-2-yl)-3-(trifluoromethyl)-4,5-dihydroisoxazolo[5,4-d]pyrimidin-6-yl)pyridin-3-yl)acetamide 
• 1094619-66-5 (R)-N-(2-(4-oxo-5-(1-phenylpropan-2-yl)-3-(trifluoromethyl)-4,5-dihydroisoxazolo[5,4-d]pyrimidin-6-yl)pyridin-3-yl)acetamide 
• 1094619-87-0 (R)-6-(3-nitropyridin-2-yl)-5-(1-phenylpropan-2-yl)-3-(trifluoromethyl)isoxazolo[5,4-d]pyrimidin-4(5H)-one 
• 99368-19-1 3-amino-N-methylpyridine-2-carboxamide 

Relevant articles and documents

Excited state tautomerization of azaindole

Fluorescent tryptophan analogs, like azatryptophan, offer an advantage for exploring protein and peptide structure and dynamics. The chromophoric moieties, azaindole, of the azatryptophan analogs are investigated for their potential as fluorescent probes. The photophysical properties of 4-azaindole (4AI) and 5-azaindole (5AI) and their tautomers are characterized through computational and experimental methods. Both 4AI and 5AI undergo excited state tautomerization in the presence of 1 M NaOH. The protonated forms of 4AI and 5AI have a fluorescence emission of 415 and 410 nm, respectively, while the tautomers of 4AI and 5AI have a fluorescent emission of 480 and 450 nm, respectively. Gas phase computations (B3LYP/6-31+G**) show that the N1H azaindole tautomer is lower in energy in the ground state by as much as 12.5 kcal mol-1, while the N″H azaindole tautomer is lower in energy in the excited state by as much as 18.1 kcal mol-1. Solvent effects on the tautomer energy differences were computed using the isodensity polarized continuum model (IPCM). The polarity of the solvent helps to reduce the energy difference between the tautomers in the ground state by as much as 5.8 kcal mol-1, but not enough to reverse the ground state tautomer preference. The Royal Society of Chemistry 2005.

Selective ortho methylation of nitroheteroaryls by vicarious nucleophilic substitution

(Chemical Equation Presented) An efficient and scalable three-step one-pot approach to 6-methyl-5-nitroisoquinoline (1) from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds. Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction pathways under VNS conditions, one leading to an isoxazole and the other resulting in the formal cyclopropanation of an aromatic nitro compound.

Method for preparing nitro compound by using graphene to catalyze nitric oxide

The invention discloses a method for preparing a nitro compound by using graphene to catalyze nitric oxide. A graphene oxide carbon material is used for catalysis of a reaction of nitric oxide and a nitrification substrate such as an aromatic compound to prepare the nitro compound. The method is used for replacing a traditional nitric acid/sulfur acid method to prepare the nitro compound, so thatthe atom utilization rate of the reaction is increased, the energy is saved, and the emission is reduced; and the method has the characteristic of atom economy during industrial preparation of the nitro compound.

3-(INDOLYL)-OR 3-(AZAINDOLYL)- 4-ARYLMALEIMIDE DERIVATIVES FOR USE IN THE TREATMENT OF COLON AND GASTRIC ADENOCARZINOMA

no abstract published

Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate

Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.

Novel 3-azaindolyl-4-arylmaleimides exhibiting potent antiangiogenic efficacy, protein kinase inhibition, and antiproliferative activity

Tumor growth and metastasis are highly associated with the overexpression of protein kinases (PKs) regulating cell growth, apoptosis resistance, and prolonged cell survival. This study describes novel azaindolyl-maleimides with significant inhibition of PKs, such as VEGFR, FLT-3, and GSK-3β which are related to carcinogenesis. Furthermore, these compounds exhibit high kinase selectivity and potent inhibition of angiogenesis and cell proliferation, offering versatile options in cancer treatment strategies.

Discovery and bioactivity of 4-(2-arylpyrido[3′,2′:3,4] pyrrolo[1,2-f][1,2,4]triazin-4-yl) morpholine derivatives as novel PI3K inhibitors

PI3K is a promising therapeutic target for cancer. With PI-103 as the lead compound, we designed and synthesized 4-(2-arylpyrido[3′,2′:3,4] pyrrolo[1,2-f][1,2,4]triazin-4-yl)morpholine derivatives. 9, 10a, 10d, 10e had the IC50 against PI3Kα comparable with PI-103. All of the compounds showed selectivity over 15 tested protein kinases and anti-proliferative activity at micromolar concentration against several cancer cell lines.

HETEROCYCLIC COMPOUNDS AND THEIR USES

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110δ activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.

3-(INDOLYL)- OR 3-(AZAINDOLYL)-4-ARYLMALEIMIDE COMPOUNDS AND THEIR USE IN TUMOR TREATMENT

The present invention relates to a compound of formula (I) wherein R, R and R are as defined in the description and the physiologically acceptable salts thereof as well as the physiologically acceptable solvates of the compounds of formula I and of the salts thereof. The compounds of formula I are suitable for treating tumors

3-(indolyl)- or 3-(azaindolyl)-4-arylmaleimide derivatives for use in the treatment of colon and gastric adenocarcinoma

The present invention relates to the use of a compound of formula (I) wherein R1, and R3 are as defined in the description and R2 is a phenyl group which is substituted with 2 or 3 C1-G6 alkoxy groups, or a physiologically acceptable salt thereof, or a solvate of the compound of formula (I) or of the salt thereof, for treatment of colorectal or gastric adenocarcinoma.