2-BROMO-5-HYDROXYBENZALDEHYDE Chemical Properties

Melting point:

130-135 °C

Boiling point:

286.7±20.0 °C(Predicted)

Density 

1.737±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in chloroform, dichloromethane and ethyl acetate.

form 

Solid

pka

8.67±0.18(Predicted)

color 

White to Gray to Brown

InChI

InChI=1S/C7H5BrO2/c8-7-2-1-6(10)3-5(7)4-9/h1-4,10H

InChIKey

SCRQAWQJSSKCFN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2973-80-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-50-22

Safety Statements 

26-36/37/39-61

RIDADR 

UN 3077

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

9

PackingGroup 

III

HS Code 

2909500090

2-BROMO-5-HYDROXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

Pale Grey Solid

Uses

2-Bromo-5-hydroxybenzaldehyde is a useful reactant used in the synthesis of PDE4 inhibitors, BCL-XL and cancel cell growth inhibitors. Also an reactant used in the preparation of many pharmaceutical agents.

Uses

2-Bromo-5-hydroxybenzadehyde is a reactant used in the preparation of many pharmaceutical agents: Bcl-XL, PDE4 inhibitors, inhibitors of prostate cancer cell growth and anti-inflamatory agents.

Synthesis

General procedure for the synthesis of 2-bromo-5-hydroxybenzaldehyde from m-hydroxybenzaldehyde: 3-hydroxybenzaldehyde (120 g, 0.98 mol) was suspended in 2400 mL of dichloromethane (CH2Cl2) in a 5 L four-necked, round-bottomed flask fitted with an overhead stirrer, a temperature probe, a dosing funnel, and a condenser tube. The mixture was heated to 35-40 °C to completely dissolve the raw material. Bromine (52 mL, 1.0 mol, 1.02 eq.) was added slowly dropwise through the addition funnel, controlling the rate of dropwise acceleration to maintain the reaction temperature between 35-38°C. After dropwise addition, the reaction mixture was stirred at 35 °C overnight. Subsequently, the mixture was slowly cooled to -5-0 °C over a period of 2 h and stirring was continued for 1 h at this temperature. The precipitated solid was collected by filtration through a Brinell funnel and the filter cake was washed with 400 mL of cold 1:1 n-heptane/dichloromethane mixture. The resulting gray solid was dried under vacuum at room temperature (0.2 mmHg). The yield was 124.3 g in 63% yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 955 - 959
[2] Patent: US2004/19018, 2004, A1. Location in patent: Page/Page column Sheet 2
[3] Journal of the Iranian Chemical Society, 2011, vol. 8, # 2, p. 531 - 536
[4] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1007 - 1009
[5] Synthetic Communications, 2007, vol. 37, # 4, p. 581 - 585

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