2-BROMO-4-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

68-69℃

Boiling point:

284℃

Density 

1.522

Flash point:

126℃

storage temp. 

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

form 

Solid

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C8H7BrO2/c1-11-7-3-2-6(5-10)8(9)4-7/h2-5H,1H3

InChIKey

ODISAUHBLBVQKC-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(OC)C=C1Br

CAS DataBase Reference

43192-31-0

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50

Safety Statements 

61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

2912490090

2-BROMO-4-METHOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

White solid

Uses

2-Bromo-4-methoxybenzaldehyde is an organic compound that is often used as an intermediate in organic synthesis, especially in pharmaceutical and pesticide chemistry.

Synthesis

The general procedure for the synthesis of 2-bromo-4-methoxybenzaldehyde from p-methoxybenzaldehyde is as follows: Example 4: Scheme C1; n-Butyl lithium (n-BuLi, 1 equiv, 147 mmol, 59 mL, 2.5 M) was slowly added dropwise to an anhydrous tetrahydrofuran (THF, 80 mL) solution of trimethylethylenediamine (TMEDA, 1.1 equiv, 162 mmol, 17.0 g) under stirring at -20 °C. After 15 min, p-methoxybenzene formaldehyde (1 eq, 147 mmol, 20.0 g) and stirring was continued for 15 min, followed by dropwise addition of n-butyllithium (n-BuLi, 3 eq, 441 mmol, 176 mL, 2.5 M). The reaction mixture was stirred at 0 °C for 20 hours. The solution was cooled to -78 °C, carbon tetrabromide (2.7 eq, 397 mmol, 131.6 g) was added, and the solution was allowed to warm slowly to room temperature. A 10% aqueous hydrochloric acid solution was added and extracted with dichloromethane. The organic extracts were combined and washed sequentially with saturated aqueous sodium thiosulfate, water and brine. The organic phase was dried with anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: heptane/ethyl acetate, 9:1) to afford the target compound C1.2 as a white solid (8 g, yield = 25%). 1H-NMR (δ, DMSO-D6): 3.89 (3H, s), 7.13 (1H, dd, J=8.7,2.4 Hz), 7.35 (1H, d, J=2.4 Hz), 7.83 (1H, d, J=8.7 Hz), 10.10 (1H, s) ppm.

References

[1] Tetrahedron, 2012, vol. 68, # 40, p. 8463 - 8471
[2] Chemical Communications, 2005, # 46, p. 5793 - 5795
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 1, p. 143 - 150
[4] Organic Letters, 2011, vol. 13, # 14, p. 3686 - 3689
[5] Patent: WO2008/37784, 2008, A1. Location in patent: Page/Page column 37

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