4-Fluoro-3-nitrobenzyl bromide Chemical Properties

Melting point:

84-86°C

Boiling point:

317.4±27.0 °C(Predicted)

Density 

1.733±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

Pale yellow

CAS DataBase Reference

15017-52-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

34-36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

1759

HS Code 

2904990090

4-Fluoro-3-nitrobenzyl bromide Usage And Synthesis

Uses

scaffold molecule for combinatorial synthesis

Synthesis

General procedure for the synthesis of 4-fluoro-3-nitrobenzyl bromide from 3-nitro-4-fluorobenzyl alcohol: 1. in a dry reaction flask, phosphorus tribromide (1.13 mL) was slowly added dropwise to a solution of 4-fluoro-3-nitrobenzyl alcohol (2.1 g, 11.23 mmol) in anhydrous ether (40 mL). 2. Stir the reaction mixture at room temperature for 1 hour until the reaction is complete. 3. After the reaction is complete, carefully add water to the reaction mixture to quench the reaction. 4. The reaction mixture was extracted with ethyl acetate (3 × 20 mL) and the organic phases were combined. 5. The organic phase was washed sequentially with saturated sodium bicarbonate solution (20 mL) and saturated brine (20 mL). 6. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the crude product. 7. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, gradient elution) to obtain 4-fluoro-3-nitrobenzyl bromide (2.50 g, 95% yield) as a light yellow solid. Product Characterization: 1H NMR (270 MHz, CDCl3) δ (ppm): 8.10 (dd, 1H, J = 7.1, 2.2 Hz), 7.67 (m, 1H), 7.29 (dd, 1H, J = 10.7, 8.6 Hz), 4.49 (s, 2H).

References

[1] Patent: EP1982982, 2008, A1. Location in patent: Page/Page column 199
[2] Patent: KR101511396, 2015, B1. Location in patent: Paragraph 2917-2921
[3] Journal of the Chemical Society - Series Chemical Communications, 1994, # 4, p. 439 - 440
[4] Heterocycles, 1999, vol. 51, # 9, p. 2041 - 2063
[5] Tetrahedron, 2011, vol. 67, # 33, p. 6073 - 6082

4-Fluoro-3-nitrobenzyl bromide(15017-52-4)Related Product Information

• Ethyl bromodifluoroacetate
• 1-Fluoro-2-nitrobenzene
• Dimidium bromide
• Bromonitromethane
• Ethidium bromide
• 4-Nitrobenzyl alcohol
• 4-Fluoronitrobenzene
• Allyl bromide
• Sodium bromate
• Vecuronium bromide
• Rocuronium bromide
• 4-Fluorobenzyl bromide
• 4-FLUORO-3-NITROBENZYL ALCOHOL 96
• 3-Fluorobenzyl bromide
• 3-Nitrobenzyl bromide
• Fluorine
• 4-Nitrobenzyl chloride
• BROMOTRIFLUOROMETHANE