4-Bromo-3-fluorobenzonitrile Chemical Properties

Melting point:

54-58 C

Boiling point:

230.1±20.0 °C(Predicted)

Density 

1.69±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C7H3BrFN/c8-6-2-1-5(4-10)3-7(6)9/h1-3H

InChIKey

QBKXYSXQKRNVRQ-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(Br)C(F)=C1

CAS DataBase Reference

133059-44-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

20/21/22-36/37/38-36-22

Safety Statements 

26-36

Hazard Note 

Toxic

HazardClass 

IRRITANT

HS Code 

2926907090

4-Bromo-3-fluorobenzonitrile Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4-Bromo-3-fluorobenzonitrile is a fluorobenzonitrile that is used in the preparation of ethylene. This chemical can also be used in the synthesis of pharmaceuticals and dyes. 4-Bromo-3-fluorobenzonitrile has been shown to have antimutagenicity and DNA repair abilities, which are due to its ability to inhibit carcinogen metabolism by binding to the enzyme cytochrome P450 2E1. 4-Bromo-3-fluorobenzonitrile also prevents cross linking of collagen by reacting with amino groups on lysine residues, which leads to a decrease in cardiac toxicity.

Synthesis

Step 2: Synthesis of 4-bromo-3-fluorobenzonitrile Sodium sulfite (0.97 g, 14.117 mmol) was added to sulfuric acid (6 mL) in batches at 5 °C, followed by stirring at room temperature for 30 min. The reaction mixture was cooled to 0 °C, acetic acid (9.8 mL) was added slowly and stirring was continued for 5 min. After that, 4-amino-3-fluorobenzonitrile (1.6 g, 11.764 mmol) was added in small portions. The mixture was stirred at room temperature for 1 hour. Subsequently, a solution of copper (I) bromide (2.5 g, 17.647 mmol) was added to the aqueous solution. Hydrobromic acid (6 mL) was added slowly at 10 °C. The resulting mixture was stirred overnight at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, water was added and extracted with ether. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (100-200 mesh) using a hexane solution containing 2% ethyl acetate as eluent, resulting in 4-bromo-3-fluorobenzonitrile (0.8 g, 34.7% yield) as a white solid. Mass spectrum (MS): 201.1 [M + 1].

References

[1] Patent: US2017/291894, 2017, A1. Location in patent: Paragraph 0536-0538

4-Bromo-3-fluorobenzonitrile(133059-44-6)Related Product Information

• 3-Fluorobenzonitrile
• DBDCB
• Chlorfenapyr
• Florfenicol
• 4-Bromofluorobenzene
• 4-Fluorobenzonitrile
• 4-Bromo-2,6-dimethylaniline
• 4-Bromo-3-fluorobenzaldehyde
• 4-Bromo-2-chlorobenzonitrile
• 4-Bromo-3-methylphenol
• 4-BROMO-2-METHYLANISOLE
• 4-Bromo-3-fluorobenzoic acid
• 4-Bromo-2-fluorobenzotrifluoride
• 4-Bromo-2-methyl-benzaldehyde
• 4-Bromo-2-fluoroanisole
• 4-BROMO-3-CHLOROPHENOL
• 4-Bromo-2-methylpyridine
• Bromine