Methyl 5-chloro-2-nitrobenzoate Chemical Properties

Melting point:

48-52 °C (lit.)

Boiling point:

306.2±22.0 °C(Predicted)

Density 

1.4530

refractive index 

1.6000 (estimate)

Flash point:

>230 °F

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow

CAS DataBase Reference

51282-49-6(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 5-chloro-2-nitro-, methyl ester (51282-49-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

36-37/39-26

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:Methyl 5-chloro-2-nitrobenzoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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Methyl 5-chloro-2-nitrobenzoate Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder or chunks

Synthesis

This embodiment relates to the synthesis of methyl 2-nitro-5-chlorobenzoate: to a stirred solution of 5-chloro-2-nitrobenzoic acid (9.393 g, 46.60 mmol) in anhydrous DMF (155 mL) at 0 °C was added potassium carbonate (K2CO3, 13.23 g, 95.72 mmol) and iodomethane (MeI, 19.38 g, 8.5 mL. 136.5 mmol), followed by slow warming of the reaction mixture to 40 °C. After 1 h of reaction, the solution was cooled to room temperature and diluted with ethyl acetate (EtOAc, 115 mL). The organic phase was washed sequentially with water (3 x 100 mL) and saturated sodium chloride solution (3 x 100 mL). The combined organic phases were dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography with 40-60% ethyl acetate/hexane as eluent to afford methyl 2-nitro-5-chlorobenzoate (9.244 g, 42.87 mmol, 92% yield) as a light yellow solid. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) and 13C NMR (100 MHz, CDCl3).

References

[1] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 9857 - 9865
[2] Patent: WO2008/156656, 2008, A2. Location in patent: Page/Page column 44; 179-180

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