1-CHLORO-5-FLUORO-2-METHYL-4-NITRO-BENZENE Chemical Properties

Melting point:

34-36℃

Boiling point:

268℃

Density 

1.417

Flash point:

116℃

storage temp. 

Sealed in dry,Room Temperature

form 

Powder

color 

Yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C7H5ClFNO2/c1-4-2-7(10(11)12)6(9)3-5(4)8/h2-3H,1H3

InChIKey

YXVJHZWHPLOEAP-UHFFFAOYSA-N

SMILES

C1(Cl)=CC(F)=C([N+]([O-])=O)C=C1C

Safety Information

HazardClass 

6.1

HS Code 

2904990090

1-CHLORO-5-FLUORO-2-METHYL-4-NITRO-BENZENE Usage And Synthesis

Uses

2-Chloro-4-fluoro-5-nitrotoluene, is used as a pharmaceutical intermediate. It is also used as Ceritinib intermediate.

Synthesis

The general procedure for the synthesis of 2-chloro-4-fluoro-5-nitrotoluene from 2-chloro-4-fluorotoluene was as follows: to a stirred concentrated solution of 2-chloro-4-fluorotoluene (2.000 g, 1.383 mmol, Aldrich, direct use), concentrated sulfuric acid (15.0 mL) was slowly added at 0°C, followed by a single addition of potassium nitrate (KNO3, 1.400 g , 1.385 mmol). The reaction mixture gradually changed to a light yellow solution, which was then warmed to 28 °C and stirred at this temperature overnight. Upon completion of the reaction, the mixture was quenched by careful pouring into ice (100 g) and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to remove the solvent. The resulting oily product was further dried under vacuum to give 2.085 g (80% yield) of the target compound 2-chloro-4-fluoro-5-nitrotoluene as an oil, which was used directly in the next step of the reaction.1H NMR (CDCl3) data were as follows: δ 2.422 (s, 3H), 7.325 (d, 1H, J=10.2 Hz), 7.973 (d, 1H, J= 5.2Hz).

References

[1] Patent: WO2005/82853, 2005, A1. Location in patent: Page/Page column 210-211
[2] Patent: WO2005/75425, 2005, A2. Location in patent: Page/Page column 184-185
[3] Patent: WO2005/82862, 2005, A2. Location in patent: Page/Page column 136
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 14, p. 5675 - 5690
[5] Patent: KR2016/147358, 2016, A. Location in patent: Paragraph 0226-0228

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