4-(bromomethyl)benzaldehyde Chemical Properties

Melting point:

99 °C

Boiling point:

277.9±15.0 °C(Predicted)

Density 

1.524±0.06 g/cm3(Predicted)

storage temp. 

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

form 

crystalline powder

color 

Pale lemon

InChI

InChI=1S/C8H7BrO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H,5H2

InChIKey

XYPVBKDHERGKJG-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(CBr)C=C1

CAS DataBase Reference

51359-78-5

Safety Information

Hazard Codes 

C

Safety Statements 

24/25

Hazard Note 

Corrosive

HS Code 

29142990

4-(bromomethyl)benzaldehyde Usage And Synthesis

Synthesis

4-(bromomethyl) benzonitrile (1 g, 5.1 mmol) was dissolved in 10 mL of dry toluene and cooled at 0 oC and a portion of 1.08 M DIBALH in hexane (2 equiv.) was added dropwise under nitrogen atmosphere. The solution was stirred for 1 h at 0 oC. The reaction mixture was first diluted with chloroform (15 mL) followed by 34 mL of 10% HCl, and the solution was stirred at room temperature for another 1 h. The organic layer separated was washed with distilled water and dried over anhydrous Na2SO4. The solvent was almost completely removed from the filtrate under reduced pressure, and the residue was washed with ice-cold n-hexane and dried at 50 oC under vacuum to afford 4-(bromomethyl)benzaldehyde. Yield: 70%; 1 H NMR (300 MHz, CDCl3, TMS): δ = 10.02 (s, 1H), 7.86 (m, 2H), 7.57 (m, 2H), 4.52 (s, 2H) ppm[1].

References

[1] Sandeep, Anjamkudy et al. “Supercoiled fibres of self-sorted donor–acceptor stacks: a turn-off/turn-on platform for sensing volatile aromatic compounds?.” Chemical Science 7 (2016): 4460–4467.

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