3-BROMO-4-HYDROXYBENZALDEHYDE Chemical Properties

Melting point:

130-135 °C (lit.)

Boiling point:

261.3±20.0 °C(Predicted)

Density 

1.737±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

6.24±0.18(Predicted)

color 

White to Pale Yellow

Water Solubility 

Soluble in water 1.33 g/L.

Sensitive 

Air Sensitive

BRN 

2205318

InChI

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

InChIKey

UOTMHAOCAJROQF-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2973-78-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 3-bromo-4-hydroxy-(2973-78-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-BROMO-4-HYDROXYBENZALDEHYDE Usage And Synthesis

Uses

3-Bromo-4-hydroxybenzaldehyde is an intermediate in organic syntheses, it is used to produce other chemicals like 5-Brom-4-hydroxy-b-nitrostyrol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 3305, 1979 DOI: 10.1021/jo01333a006

Synthesis

General procedure for the synthesis of 3-bromo-4-hydroxybenzaldehyde from 2-bromo-4-methylphenol: A mixture of the substrate 2-bromo-4-methylphenol (1 mmol), cobalt salt (n1 mol%), and NaOH (n2 eq.) in ethylene glycol (5 mL) was stirred with oxygen (1 atm) and bubbled for 8 hr at 80 °C. Upon completion of the reaction, hydrochloric acid (10 mL, 2%) and methyl tert-butyl ether (MTBE, 10 mL) were added sequentially to the reaction mixture. The organic layer was separated and the aqueous phase was further extracted with MTBE (10 mL x 2). All organic phases were combined and concentrated by drying with anhydrous sodium sulfate to give the residue. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 10/1) to afford the target product 3-bromo-4-hydroxybenzaldehyde.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1406 - 1411
[2] Green Chemistry, 2014, vol. 16, # 5, p. 2807 - 2814
[3] Green Chemistry, 2014, vol. 16, # 3, p. 1248 - 1254
[4] Research on Chemical Intermediates, 2015, vol. 41, # 6, p. 3855 - 3863
[5] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 45 - 49

3-BROMO-4-HYDROXYBENZALDEHYDE(2973-78-6)Related Product Information

• 2-BROMO-5-HYDROXYBENZALDEHYDE
• 3-BROMO-2-HYDROXYBENZALDEHYDE
• 4-Bromo-2-hydroxybenzaldehyde
• 3',5'-Dibromo-4'-hydroxyacetophenone
• 5-Bromovanillin
• 3,5-Dibromo-4-hydroxybenzaldehyde
• METHYL 3,5-DIBROMO-2,4-DIHYDROXY-6-METHYLBENZOATE
• METHYL 3,5-DIBROMO-2,4-DIMETHOXY-6-METHYLBENZOATE
• 3-BROMO-4-HYDROXYBENZOIC ACID HYDRATE
• 3,5-Dibromo-4-hydroxybenzoic acid
• 5-BROMO-2,4-DIHYDROXYBENZOIC ACID
• 3-BROMO-4-HYDROXYBENZALDEHYDE
• 3-Bromo-4-methoxybenzaldehyde
• 2,3-DIBROMO-4-HYDROXY-5-METHOXYBENZALDEHYDE
• METHYL 3,5-DIBROMO-4-HYDROXYBENZOATE
• Benzbromarone
• 3,5-Dibromosalicylaldehyde
• 5-Bromo-2-anisaldehyde