5-Formylsalicylic acid Chemical Properties

Melting point:

250 °C (dec.) (lit.)

Boiling point:

214.32°C (rough estimate)

Density 

1.2208 (rough estimate)

refractive index 

1.4611 (estimate)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder

pka

2.67±0.10(Predicted)

color 

brownish-yellow

BRN 

2640881

Stability:

Hygroscopic

InChI

InChI=1S/C8H6O4/c9-4-5-1-2-7(10)6(3-5)8(11)12/h1-4,10H,(H,11,12)

InChIKey

UTCFOFWMEPQCSR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

616-76-2(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29189900

MSDS

• Language:English Provider:2-Hydroxy-5-formylbenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Formylsalicylic acid Usage And Synthesis

Chemical Properties

light beige fine crystalline powder

Uses

5-Formylsalicylic Acid is used as a selective phase for the extraction of iron(III) in silica gel. It is also used in preparation of styrylquinolines as potent HIV-1 integrase inhibitors that block HIV-1 replication in CEM cells.

Definition

ChEBI: 5-formylsalicylic acid is a monohydroxybenzoic acid in which a benzoic acid nucleus is substituted at positions 2 and 5 by a formyl group and an hydroxy group respectively. It is a member of benzaldehydes, a monohydroxybenzoic acid and a member of phenols. It is functionally related to a salicylic acid.

Synthesis

General procedure for the synthesis of 5-formyl-2-hydroxybenzoic acid from 5-methylsalicylic acid: a mixture of the substrate 5-methylsalicylic acid (1 mmol), cobalt salt (n1 mol%), and NaOH (n2 eq.) in ethylene glycol (5 mL) was reacted with oxygen (1 atm) with stirring for 8 hours 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). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated 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 5-formyl-2-hydroxybenzoic acid.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1406 - 1411
[2] Molecular Catalysis, 2018, vol. 453, p. 121 - 131

5-Formylsalicylic acid(616-76-2)Related Product Information

• Benzoyl peroxide
• Carbachol
• Calcium folinate
• Ethyl 2-(Chlorosulfonyl)acetate
• Salicylic acid
• Sodium salicylate
• 4-Formylbenzoic acid
• 2-Carboxybenzaldehyde
• P-AMINOBENZAMIDE GLUTAMIC ACID
• 5-Methylsalicylic acid
• CHLOROPHOSPHONAZO III
• Folic acid
• Tetrahydro-4H-pyran-4-one
• Dibenzoylmethane
• Citric acid
• Ascoric Acid
• METHYL 5-ACETYLSALICYLATE
• Dibenzoyltartaric acid