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2-Bromo-6-fluorobenzonitrile

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2-Bromo-6-fluorobenzonitrile Basic information

Product Name:
2-Bromo-6-fluorobenzonitrile
Synonyms:
  • 6-BROMO-2-FLUOROBENZONITRILE
  • 2-FLUORO-6-BROMOBENZONITRILE
  • 2-BROMO-6-FLUOROBENZONITRILE
  • 2-Cyano-3-Fluoro-1-broMobenzene
  • 3-bromo-2-cyanofluorobenzene
  • 2- fluoro-6-bromoxynil
  • 2-Bromo-6-fluorobenzotrile
  • 2-Bromo-6-fluorobenzonitrile >
CAS:
79544-27-7
MF:
C7H3BrFN
MW:
200.01
Product Categories:
  • Fluorine series
  • cyanide| alkyl bromide| alkyl Fluorine
  • Aromatic Nitriles
  • Nitrile
  • C6 to C7
  • Cyanides/Nitriles
  • Nitrogen Compounds
Mol File:
79544-27-7.mol
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2-Bromo-6-fluorobenzonitrile Chemical Properties

Melting point:
60-61
Boiling point:
254.6±25.0 °C(Predicted)
Density 
1.69±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Solid
color 
White to brown
InChIKey
IELGUZKHALDFOO-UHFFFAOYSA-N
CAS DataBase Reference
79544-27-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T,Xi,Xn
Risk Statements 
22-36/37/38
Safety Statements 
26
WGK Germany 
3
Hazard Note 
Toxic
HazardClass 
IRRITANT-HARMFUL
HazardClass 
6.1
HS Code 
2926907090
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2-Bromo-6-fluorobenzonitrile Usage And Synthesis

Chemical Properties

Off-white crystalline

Uses

2-Bromo-6-fluorobenzonitrile is used as an initial raw material in the synthesis of  2-bromo-6-fluorobenzoic acid.

Synthesis

2-Amino-6-fluorobenzonitrile (18.0 g, 132 mmol) was dissolved in hot 1,4-dioxane (20 ml), 48% hydrobromic acid (200 ml) was added and the mixture cooled to 0°C before dropwise addition of sodium nitrite (10.5 g, 152 mmol) in water (20 ml) over 1.5 h. The resulting mixture was stirred at 0°C for 1.5 h then poured onto a cooled (0°C) solution of copper(I) bromide (56.8 g, 396 mmol) in 48% hydrobromic acid (50 ml). The solution was stirred at 0°C for 15 min then heated at 50°C for 20 min. The mixture was cooled to ambient temperature, diluted with water (1200 ml) and extracted with ethyl acetate (2 x 400 ml). The combined organics were washed with 10% aqueous ammonia solution (400 ml), water (400 ml) and brine (500 ml), dried over anhydrous magnesium sulfate, filtered and evaporated to give an orange oil. Purification by chromatography on silica 5 gel eluting with isohexane on a gradient of ethyl acetate (2-4%) gave 2-bromo-6-fluorobenzonitrile. White solid, yield (18.5 g, 70%). δH (400 MHz, CDCl3) 7.17-7.23 (1H, ddd, J 8, 8 and 1), 7.44-7.52 (2H, m).

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