3-Bromo-2-hydroxybenzaldehyde Chemical Properties

Melting point:

53-57

Boiling point:

215.6±20.0 °C(Predicted)

Density 

1.737±0.06 g/cm3(Predicted)

Flash point:

>110

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

6?+-.0.10(Predicted)

color 

Light yellow to Amber to Dark green

InChI

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

InChIKey

STBGLXMINLWCNL-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=CC(Br)=C1O

CAS DataBase Reference

1829-34-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

29130000

3-Bromo-2-hydroxybenzaldehyde Usage And Synthesis

Application

3-Bromo-2-hydroxybenzaldehyde can be used as a drug molecule and an intermediate in organic synthesis in the laboratory.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 41, p. 1166, 1993 DOI: 10.1248/cpb.41.1166

Synthesis

The general procedure for the synthesis of 3-bromo-2-hydroxybenzaldehyde using 7-bromo-2-methylbenzofuran as starting material was as follows: first, a stirred solution of some of the B compounds (1.94 g, 9.19 mmol) in dichloromethane (100 mL) was cooled to -78 °C through a calcium chloride drying tube, and then the 3% O3/O2 gas mixture was passed through until the solution took on a persistent blue color (ca. 35 min). Subsequently, the solution was purged with nitrogen, dimethyl sulfide (5 mL) was added, and the reaction mixture was slowly warmed to room temperature. After 4 hours of reaction, the solvent was evaporated and the residue was redissolved. Next, water (8 mL) and potassium carbonate (1.1 g, 80 mmol) were added to methanol (8 mL), and the mixture was heated to 55 °C for 1 h under argon protection. Upon completion of the reaction, the mixture was cooled, neutralized to pH 7 with 1 M bisulfate solution, and then extracted twice with dichloromethane. The organic phases were combined, dried with magnesium sulfate and the solvent was evaporated. Finally, purification by fast chromatography afforded 3-bromo-2-hydroxybenzaldehyde as a light yellow crystalline solid in a yield of 1.47 g (80% yield).LC/MS analysis showed that the molecular ion peak of the target compound [(M+H)+ = 201] was in agreement with expectations.

References

[1] Patent: US2003/225091, 2003, A1. Location in patent: Page 29
[2] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 6, p. 1166 - 1168
[3] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 6, p. 1166 - 1168

3-Bromo-2-hydroxybenzaldehyde(1829-34-1)Related Product Information

• Cuminaldehyde
• 3-Hydroxybenzaldehyde
• 4-Hydroxybenzaldehyde
• 4-Dimethylaminobenzaldehyde
• 4-Bromo-2-hydroxybenzaldehyde
• Benzaldehyde
• 2,4-Dihydroxybenzaldehyde
• p-Tolualdehyde
• Salicylaldehyde
• p-Anisaldehyde
• 3,5-Dibromosalicylaldehyde
• Bromine
• 3-Bromo-5-chlorosalicylaldehyde
• 3,5,4'-TRIBROMOSALICYLANILIDE
• METHYL 3,5-DIBROMO-2-HYDROXYBENZOATE
• 3-BROMO-2,6-DIMETHOXYBENZOIC ACID
• 5-BROMO-2-HYDROXYBENZALDEHYDE,5-BROMOSALICYLALDEHYDE / 5-BROMO-2-HYDROXYBENZALDEHYDE
• 3-BROMO-4-HYDROXYBENZALDEHYDE,3-Bromo-4-hydroxybenzaldehyde, 98+%