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2-Methyl-3-nitropyridine

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CAS:18699-87-1
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CAS:18699-87-1
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Products Intro: Product Name:2-Methyl-3-nitropyridine
CAS:18699-87-1
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2-Methyl-3-nitropyridine Basic information
Product Name:2-Methyl-3-nitropyridine
Synonyms:3-NITRO-2-PICOLINE;3-NITRO-2-METHYLPYRIDINE;2-METHYL-3-NITROPYRIDINE;2-Methyl-3-nitropyri;Pyridine, 2-methyl-3-nitro- (9CI);3-Nitro-2-methylpyridine 3-Nitro-2-picoline;2-METHYL-3-NITROPYRIDINE 95%;3-NITROPICOLINE
CAS:18699-87-1
MF:C6H6N2O2
MW:138.12
EINECS:805-108-9
Product Categories:Pyridines;Pyridine;NITRO
Mol File:18699-87-1.mol
2-Methyl-3-nitropyridine Structure
2-Methyl-3-nitropyridine Chemical Properties
Melting point 32-33°
Boiling point 86°C/5mmHg(lit.)
density 1.246±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
solubility soluble in Methanol
form powder to lump
pka1.92±0.10(Predicted)
color Light yellow to Brown
InChIInChI=1S/C6H6N2O2/c1-5-6(8(9)10)3-2-4-7-5/h2-4H,1H3
InChIKeyCCFGTKQIRWHYTB-UHFFFAOYSA-N
SMILESC1(C)=NC=CC=C1[N+]([O-])=O
CAS DataBase Reference18699-87-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
HazardClass IRRITANT
HS Code 2933399990
MSDS Information
2-Methyl-3-nitropyridine Usage And Synthesis
Uses2-Methyl-3-nitropyridine is used as a starting reagent to synthesize 3-substituted-4 or 6-azaindoles, and is also used as a reagent to prepare 3-azaindolyl-4-arylmalemides (compounds that exhibit antiproliferative activity).
Reactions2-Methyl-3-nitropyridine could be used to synthesize dichloro-(3-nitro-2-pyridyl)methylphosphonic dichloride. The chlorination of 2-methyl-3-nitropyridine using a mixture of PCl5 in POCl3[1].
2-Methyl-3-nitropyridine
Synthesis Reference(s)Tetrahedron, 54, p. 6311, 1998 DOI: 10.1016/S0040-4020(98)00328-7
Journal of Heterocyclic Chemistry, 29, p. 359, 1992 DOI: 10.1002/jhet.5570290213
Synthetic Communications, 20, p. 2965, 1990 DOI: 10.1080/00397919008051513
SynthesisSuzuki Reaction. A mixture of 2-chloro-3-nitro-pyridine 1 (793 mg, 5 mmol), methylboronic acid (329 mg, 5.5 mmol), Pd(PPh3) 4 (578 mg, 0.5 mmol) and K2CO 3 (2.073 g, 15 retool) in dioxane (25 mL) was refluxed for 2 days, then cooled to room temperature and filtered. The solvent was removed and the residue was isolated by chromatography (hexanes-EtOAc = 1:1) to provide 623 mg (90%) of 2-methyl-3-nitropyridine[2].
References[1] Amrane D, et al. "Dichloro{4-(4-chlorophenoxy)phthalazin-1-yl} methylphosphonic dichloride." Molbank (2022).
[2] Niu, Chuansheng , et al. "Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)." 54.23(1998):6311-6318.
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