2-Chloro-4-methyl-5-nitropyridine Chemical Properties

Melting point:

37-39 °C (lit.)

Boiling point:

91 °C/5 mmHg (lit.)

Density 

1.5610 (rough estimate)

refractive index 

1.5870 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Crystalline Powder or Chunks

pka

-3.42±0.10(Predicted)

color 

Light cream to light brown

InChI

InChI=1S/C6H5ClN2O2/c1-4-2-6(7)8-3-5(4)9(10)11/h2-3H,1H3

InChIKey

HWZUMEVIIGNXGM-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C([N+]([O-])=O)C(C)=C1

CAS DataBase Reference

23056-33-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36/37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Chloro-4-methyl-5-nitropyridine Usage And Synthesis

Chemical Properties

light cream to light brown crystalline powder

Uses

2-Chloro-4-methyl-5-nitropyridine may be used in chemical synthesis studies.

Synthesis

General procedure for the synthesis of 2-chloro-5-nitro-4-methylpyridine from 2-hydroxy-4-methyl-5-nitropyridine: 1. 2-Hydroxy-4-methyl-5-nitropyridine (500 mg, 3.24 mmol), POCl3 (0.5 mL) and PCl5 (200 mg) were mixed and stirred at 150°C for 2 hrs. 2. After completion of the reaction, cooled to room temperature, the reaction mixture was poured into ice and extracted with dichloromethane (DCM, 3 x 20 mL). 3. The organic phases were combined, washed with water to pH 7, dried over Na2SO4 and concentrated under reduced pressure. 4. The obtained residue was dried under reduced pressure to give the crude product 2-chloro-4-methyl-5-nitropyridine (480 mg, 86% yield). In the presence of PdCl2(PPh3)2 (42 mg, 0.06 mmol), P(t-Bu)3 (16 mg, 0.08 mmol) and TEA (1.5 mL), 2-chloro-4-methyl-5-nitropyridine (172 mg, 1.00 mmol) was mixed with 3-ethynyl-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one (199 mg, 1.00 mmol) in DMF (3 mL) at 100°C for 3 hours. The crude product was purified by column chromatography (silica gel) to afford the intermediate 7,7-dimethyl-3-((4-methyl-5-nitropyridin-2-yl)ethynyl)-7,8-dihydroquinolin-5(6H)-one (115 mg, 34% yield). A solution of 7,7-dimethyl-3-((4-methyl-5-nitropyridin-2-yl)ethynyl)-7,8-dihydroquinolin-5(6H)-one (114 mg, 0.34 mmol) and SnCl2-2H2O (380 mg, 1.70 mmol) in EtOH (10 mL) was stirred at reflux for 6 hours. After completion of the reaction, it was cooled to room temperature, poured into ice, adjusted to pH 7-8 with saturated aqueous NaHCO3 solution and extracted with EtOAc (3 × 30 mL). The organic phases were combined, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by washing with hexane and acetonitrile to afford the target product 2-chloro-5-nitro-4-methylpyridine (60 mg, 58% yield). 1H NMR (DMSO-d6) δ: 1.07 (s, 6H), 2.08 (s, 3H), 2.60 (s, 2H), 3.02 (s, 2H), 5.51 (s, 2H), 7.23 (s, 1H), 7.90 (s, 1H), 8.17 (s, 1H), 8.80 (s, 1H). LC/MS (M+H)+ = 306.

References

[1] Patent: WO2012/52451, 2012, A1. Location in patent: Page/Page column 117-118
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
[3] Journal of the Chemical Society, 1954, p. 1190,1192
[4] Journal of the Chemical Society, 1954, p. 2448,2455
[5] Patent: WO2007/53394, 2007, A1. Location in patent: Page/Page column 12

2-Chloro-4-methyl-5-nitropyridine(23056-33-9)Related Product Information

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