5-Bromo-1,3-difluoro-2-nitrobenzene Chemical Properties

Boiling point:

266 °C

Density 

1.890

Flash point:

114 °C

storage temp. 

2-8°C

form 

powder

color 

Faint yellow to orange

InChI

InChI=1S/C6H2BrF2NO2/c7-3-1-4(8)6(10(11)12)5(9)2-3/h1-2H

InChIKey

ABAGKHWCTWMUDH-UHFFFAOYSA-N

SMILES

C1(F)=CC(Br)=CC(F)=C1[N+]([O-])=O

Safety Information

HS Code 

2904990090

5-Bromo-1,3-difluoro-2-nitrobenzene Usage And Synthesis

Application

5-Bromo-1,3-difluoro-2-nitrobenzene is mainly used as an intermediate in organic synthesis and pharmaceutical chemistry, and can be used in the synthesis of drug molecules and bioactive molecules. In organic synthesis transformations, its bromine atom can undergo a Suzuki coupling reaction with arylboronic acids or borate esters catalyzed by the transition metal palladium.

Synthesis

Sodium perborate tetrahydrate (18.5 g, 0.12 mol, 5.0 eq) was suspended in glacial acetic acid (125 mL) and heated to 65 °C. 4-Bromo-2,6-difluoroanilline(5.0 g, 24.0 mmol, 1.0 eq) dissolved in glacial acetic acid (50 mL) was added slowly through a funnel over 4 h. After the addition, the reaction mixture was heated for 3 h additional hours before a second portion of NaBO3·4H2O (6.0 g, 30.0 mmol) was added. Then, the mixture was stirred for 14 h, and a third portion of oxidating agent (9.0 g, 45.0 mmol) was added. 9 h after the third addition full consumption of the starting material was indicated by TLC. After cooling the mixture to room temperature, the formed solid was removed by filtration. The filtrate was poured into ice-cold water (300 mL). The precipitated solid was filtered off and dried to give the product 5-Bromo-1,3-difluoro-2-nitrobenzene as a yellow solid (3.40 g 60percent).

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3364 - 3386
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6686 - 6690
[3] Patent: WO2007/36715, 2007, A2. Location in patent: Page/Page column 51
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 17, p. 5243 - 5263
[5] European Journal of Medicinal Chemistry, 2016, vol. 107, p. 97 - 108

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