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

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 Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933399990

2-Methyl-3-nitropyridine Usage And Synthesis

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].

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.

2-Methyl-3-nitropyridine(18699-87-1)Related Product Information

• 2,6-Lutidine
• Azamethiphos
• Methyl acetate
• METSULFURON METHYL
• Bensulfuron methyl
• Kresoxim-methyl
• Methylparaben
• 2,4,6-Collidine
• Methyl acrylate
• 2-Bromo-5-nitropyridine
• Thiophanate-methyl
• 4-Methylpyridine
• Methyl
• nitrotoluene
• Parathion-methyl
• 2-Methyl-4-nitropyridine
• 2-AMINO-5-NITRO-6-PICOLINE (2-AMINO-6-METHYL-5-NITROPYRIDINE)
• Methyl bromide