3,5-Dibromosalicylaldehyde Chemical Properties

Melting point:

82-83.5 °C (lit.)

Boiling point:

261.2±35.0 °C(Predicted)

Density 

1.9661 (rough estimate)

refractive index 

1.4970 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

methanol: soluble25mg/mL, clear, yellow to brown

pka

6.08±0.23(Predicted)

form 

Crystalline Powder

color 

Yellow to yellow-brown

Water Solubility 

Soluble in methanol 25 mg/mL. Insoluble in water.

Sensitive 

Air Sensitive

Merck 

14,3027

BRN 

1424739

InChIKey

JHZOXYGFQMROFJ-UHFFFAOYSA-N

CAS DataBase Reference

90-59-5(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Dibromosalicylaldehyde(90-59-5)

EPA Substance Registry System

Benzaldehyde, 3,5-dibromo-2-hydroxy- (90-59-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

RTECS 

CU5609000

HazardClass 

9

PackingGroup 

III

HS Code 

29130000

MSDS

• Language:English Provider:3,5-Dibromo-2-hydroxybenzaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3,5-Dibromosalicylaldehyde Usage And Synthesis

Chemical Properties

yellow to yellow-brown crystalline powder.
3,5-Dibromosalicylaldehyde has an aromatic odor, and like salicylaldehyde, the compound colors the skin bright yellow. It is readily soluble in ether, benzene, chloroform, and hot alcohol. It imparts a yellow colour to cold water and is slightly soluble in boiling water, so it may be purified by distillation with steam. With the addition of sodium hydroxide, the brilliant yellow sodium salt separates; it is difficultly soluble in cold water or alcohol but more readily soluble when heated with these solvents.

Uses

3,5-Dibromosalicylaldehyde reacts with alkyl cyanoacetates in the presence of ammonium acetate to yield 4H- chromenes. It can be used in the synthesis of Schiff base and can be used as reactant for synthesis of Schiff base ligands which forms mononuclear complexes with copper(II), nickel(II), zinc(II) and cobalt(II).

General Description

3,5-Dibromosalicylaldehyde reacts with alkyl cyanoacetates in the presence of ammonium acetate to yield 4H- chromenes.

Synthesis

3,5-Dibromosalicylaldehyde was obtained in nearly quantitative yield by dissolving 20 g. of salicylaldehyde in 100 cc. of glacial acetic acid, and adding a solution of 20 cc in small portions. of bromine in 100 cc. of glacial acetic acid[1].

References

[1] Brewster, C. M. “SCHIFF’S BASES FROM 3,5-DIBROMO-SALICYLALDEHYDE.” Journal of the American Chemical Society 46 11 (1924): 2463–2468.

3,5-Dibromosalicylaldehyde(90-59-5)Related Product Information

• Salicylaldoxime
• Salicylaldehyde
• 5-Bromosalicylaldehyde
• METHYL 3,5-DIBROMO-2,4-DIMETHOXY-6-METHYLBENZOATE
• METHYL 3,5-DIBROMO-2-HYDROXYBENZOATE
• 3,5,4'-TRIBROMOSALICYLANILIDE
• METHYL 3,5-DIBROMO-2,4-DIHYDROXY-6-METHYLBENZOATE
• 3',5'-Dibromo-2'-hydroxyacetophenone
• 3,5-Dibromosalicylic acid
• ETHYL 3,5-DIBROMO-2,4-DIHYDROXY-6-METHYLBENZOATE
• 3,5-Dibromosalicylaldehyde oxime
• 3,5-Dibromobenzaldehyde
• 3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE
• 6,8-DIBROMO-3-FORMYLCHROMONE, 99%
• METHYL 3,5-DIBROMO-2-METHOXYBENZOATE
• 3,5-DIBROMOSALICYLAMIDE
• Flusalan
• 4'-CHLORO-6,8-DIBROMOFLAVONE