2-Methyl-3-nitropyridine

CAS NO.：18699-87-1
Empirical Formula: C6H6N2O2
Molecular Weight: 138.12
MDL number: MFCD04114137
EINECS: 805-108-9
SAFETY DATA SHEET (SDS)
Update Date: 2023-11-06 17:01:50

What is 2-Methyl-3-nitropyridine?

The Uses of 2-Methyl-3-nitropyridine

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.

Properties of 2-Methyl-3-nitropyridine

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
CAS DataBase Reference	18699-87-1(CAS DataBase Reference)

Safety information for 2-Methyl-3-nitropyridine

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention.