4-Bromo-2-iodobenzaldehyde Chemical Properties

Boiling point:

323.2±37.0 °C(Predicted)

Density 

2.231±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder

color 

Off white to faint cream

InChI

InChI=1S/C7H4BrIO/c8-6-2-1-5(4-10)7(9)3-6/h1-4H

InChIKey

JFFYPBIPKMTEEQ-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(Br)C=C1I

Safety Information

HS Code 

2913000090

4-Bromo-2-iodobenzaldehyde Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-bromo-2-iodobenzaldehyde (17b) from 4-bromo-1-(bromomethyl)-2-iodobenzene: A solution of N-methylmorpholine-N-oxide (2.81 g, 23.2 mmol) and 4A molecular sieves (19 g) in acetonitrile (60 mL) was added to a dry 250 mL Schlenk flask under nitrogen protection and cooled to 0 °C. This was followed by rapid addition of benzyl bromide 15b (2.9 g, 7.7 mmol). The reaction mixture was kept at 0 °C for 2 h and then slowly warmed up to room temperature. Upon completion of the reaction, it was filtered through a short column of silica gel (SiO2:hexane) to afford the off-white solid product 17b (2.15 g, 6.92 mmol, 90% yield). The product was characterized as follows: 1H-NMR (400 MHz, CDCl3) δ: 9.99 (s, 1H), 8.13 (d, 1H, J = 0.8 Hz), 7.73 (dd, 1H, J = 8.3, 0.8 Hz), 7.61 (dd, 1H, J = 8.3, 0.8 Hz); 13C-NMR (100 MHz, CDCl3) δ: 194.7, 142.8, 134.1, 132.3, 131.1, 130.2, 100.9; HRMS (EI) m/z calculated value of C7H4BrIO [M?]+: 309.8490, measured value: 309.8489.

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2227 - 2239
[2] Synthesis, 2011, # 15, p. 2387 - 2391
[3] Patent: WO2011/127383, 2011, A2. Location in patent: Page/Page column 75

4-Bromo-2-iodobenzaldehyde(1261470-87-4)Related Product Information

• (4-Bromo-2-iodophenyl)methanol
• (2-AMINO-5-IODOPHENYL)METHANOL
• methyl 3-bromo-5-(trifluoromethoxy)benzoate
• 3-Bromo-5-(trifluoromethoxy)Benzoicacid
• methyl 2-bromo-3-chlorobenzoate
• 3-Bromobenzaldehyde
• 3,4-Dibromobenzaldehyde
• 2,4-dibromobenzaldehyde