4-BROMO-2,5-DIFLUORONITROBENZENE

4-BROMO-2,5-DIFLUORONITROBENZENE Property

Melting point:

55 °C

Boiling point:

262.4±35.0 °C(Predicted)

Density 

1.890±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

Light orange to Yellow to Green

BRN 

7411347

CAS DataBase Reference

167415-27-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-36/37

Hazard Note 

Irritant

HazardClass 

IRRITANT, TOXIC

HS Code 

29042090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P501Dispose of contents/container to..…

4-BROMO-2,5-DIFLUORONITROBENZENE Chemical Properties,Usage,Production

Chemical Properties

light yellow solid

Synthesis

General procedure for the synthesis of 4-bromo-2,5-difluoronitrobenzene from 2,5-difluorobromobenzene: Referring to Example-50, a mixture of acids was prepared by cooling concentrated sulfuric acid (57 mL) in an ice bath, followed by the slow dropwise addition of 69% nitric acid (25.5 g, 279 mmol) over a period of 25 minutes. A dichloroethane (125 mL) solution of 2-bromo-1,4-difluorobenzene (50 g, 254 mmol) was added slowly dropwise over 1.5 h to the above mixed acid under ice bath cooling conditions. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction solution was slowly poured into ice water (500 g) and extracted with ether (300 mL x 2). The organic phases were combined and washed sequentially with water (300 mL), saturated aqueous sodium bicarbonate solution (300 mL) and saturated saline (300 mL). The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography (eluent: hexane/chloroform=4:1) to afford 1-bromo-2,5-difluoro-4-nitrobenzene (56 g, yield: 93%) as a pale yellow solid.1H-NMR (400 MHz, CDCl3): δ 7.59 (dd, J=9.5 and 5.5 Hz, 1H), 7.89 (dd, J=7.3 and 6.5 Hz, 1H).19F-NMR (376 MHz, CDCl3): δ -120.1 (d, J=15.2 Hz, 1F), -107.9 (d, J=15.2 Hz, 1F).

References

[1] Patent: US2016/24110, 2016, A1. Location in patent: Paragraph 0809; 0810
[2] Patent: JP2016/56157, 2016, A. Location in patent: Paragraph 0164; 0168
[3] Patent: JP2016/60742, 2016, A. Location in patent: Paragraph 0251
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4367 - 4379
[5] Journal of Organic Chemistry, 1995, vol. 60, # 18, p. 5838 - 5842