2-Chloro-4-methyl-3-nitropyridine Chemical Properties

Melting point:

51-53 °C (lit.)

Boiling point:

279.6±35.0 °C(Predicted)

Density 

1.406±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

-1.80±0.10(Predicted)

form 

Powder

color 

Yellow to beige

Sensitive 

Hygroscopic

InChI

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

InChIKey

JHARVUVBTAAPLA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

23056-39-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-21/22

Safety Statements 

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

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333999

MSDS

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

2-Chloro-4-methyl-3-nitropyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Chloro-4-methyl-3-nitropyridine is a cyclopropyldipyridodiazepinone derivative for use as non-nucleoside reverse transcriptase inhibitors.

Definition

2-Chloro-4-methyl-3-nitropyridine (2C4M3NP) is a nitropyridine derivative that could form an acceptor fragment of 2-adamantylamino-5-nitropyridine (AANP). This crystal shows a particularly large optical non-linearity. It is observed that the mean C-C (ring) bond distance calculated between the ring carbon atoms of 2C4M3NP is 1.387 Å. In X-ray data of pyridine, the mean C-C (ring) bond distance is 1.394 Å. The C-H bond distances are found to be 1.081 Å. The computed values of C-C (ring) and C-H are slightly higher than that of the experimental value. This is attributed to the substituents present in the pyridine. The C-C-C bond angle where the -Cl and -NO2 group is attached with the middle carbon is more than 120^? while the C-C-C bond angle where the -CH3 is substituted is less than 120^? in 2C4M3NP. The N-C-CH3 bond angle (116.3^。) is less than that of the C-C-CH3 (124.2^。) probably due to the weak hydrogen bond formed between the nitrogen and hydrogen of the methyl group[1].

General Description

Experimental FTIR and FT-Raman spectroscopic analysis of 2-chloro-4-methyl-3-nitropyridine was reported.

Synthesis

General procedure for the synthesis of 2-chloro-4-methyl-3-nitropyridine from 2-keto-3-nitro-4-methylpyridine: 2-keto-3-nitro-4-methylpyridine (13 g, 0.084 mol) was added to 50 mL of phosphorochloridic acid chloride and heated to reflux for 4 hours. Upon completion of the reaction, the excess phosphorus trichloride was removed by distillation. The crude product was recrystallized in 50 mL of 75% ethanol solution to give 11 g of white solid product in 75.3% yield. The melting point of the product was 51.7-52.1 °C (ethanol), which is consistent with the values reported in the literature (52.0-52.9 °C) [J.O.C., 1955, 20, 1729-1731].

References

[1] Arjunan, V. , et al. "A comparative study on vibrational, conformational and electronic structure of 2-chloro-4-methyl-3-nitropyridine and 2-chloro-6-methylpyridine." Spectrochimica Acta Part A Molecular & Biomolecular Spectroscopy 92.none(2012):305-317.

2-Chloro-4-methyl-3-nitropyridine(23056-39-5)Related Product Information

• Methyl acrylate
• 2-Chloro-4-picoline
• Methyl acetate
• 4-Methyl-3-nitropyridine
• Bensulfuron methyl
• 2-Methyl-3-nitropyridine
• 3-Nitropyridine
• Kresoxim-methyl
• Methylparaben
• 2-Chloro-4-nitropyridine
• 2-Bromo-5-nitropyridine
• Azamethiphos
• 2,6-Lutidine
• 2,4,6-Collidine
• 2-Chloro-3-nitropyridine
• Methyl propyl carbonate
• Thiophanate-methyl
• 2-Chloro-5-chloromethylpyridine