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18699-87-1

18699-87-1 Structure

18699-87-1 Structure
IdentificationMore
[Name]

2-Methyl-3-nitropyridine
[CAS]

18699-87-1
[Synonyms]

2-METHYL-3-NITROPYRIDINE
3-NITRO-2-METHYLPYRIDINE
3-NITRO-2-PICOLINE
Pyridine, 2-methyl-3-nitro-(9CI)
3-Nitro-2-methylpyridine 3-Nitro-2-picoline
2-METHYL-3-NITROPYRIDINE 95%
3-NITROPICOLINE
[EINECS(EC#)]

805-108-9
[Molecular Formula]

C6H6N2O2
[MDL Number]

MFCD04114137
[Molecular Weight]

138.12
[MOL File]

18699-87-1.mol
Chemical PropertiesBack Directory
[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
[pka]

1.92±0.10(Predicted)
[color ]

Light yellow to Brown
[InChI]

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

CCFGTKQIRWHYTB-UHFFFAOYSA-N
[SMILES]

C1(C)=NC=CC=C1[N+]([O-])=O
[CAS DataBase Reference]

18699-87-1(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

2-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).
[Reactions]

2-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
[Synthesis]

Suzuki 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.
Spectrum DetailBack Directory
[Spectrum Detail]

2-Methyl-3-nitropyridine(18699-87-1)1HNMR
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