5-Formylsalicylic acid

Base Information

• Chemical Name: 5-Formylsalicylic acid
• CAS No.: 616-76-2
• Molecular Formula: C8H6O4
• Molecular Weight: 166.133
• Hs Code.: 29189900
• European Community (EC) Number: 210-492-0
• NSC Number: 16527,15046
• UNII: 23V3W745T8
• DSSTox Substance ID: DTXSID60210608
• Nikkaji Number: J62.828J
• Wikidata: Q72479460
• ChEMBL ID: CHEMBL229240
• Mol file: 616-76-2.mol

Synonyms:3-formylsalicylic acid;5-formylsalicylic acid

Chemical Property of 5-Formylsalicylic acid

Chemical Property:

• Appearance/Colour: light beige fine crystalline powder
• Vapor Pressure: 7.53E-06mmHg at 25°C
• Melting Point: 250 °C (dec.)(lit.)
• Refractive Index: 1.4611 (estimate)
• Boiling Point: 361.2 °C at 760 mmHg
• PKA: 2.67±0.10(Predicted)
• Flash Point: 186.5 °C
• PSA: 74.60000
• Density: 1.482 g/cm³
• LogP: 0.90290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 166.02660867
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

5-Formylsalicylic Acid >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=O)C(=O)O)O
• 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.

Technology Process of 5-Formylsalicylic acid

There total 20 articles about 5-Formylsalicylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

5-Methylsalicylic acid (89-56-5) → 2-hydroxy-5-formylbenzoic acid (616-76-2)

Guidance literature:

With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide; In ethylene glycol; at 80 ℃; for 8h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2013.12.077

Reference yield: 73.0%

m-formylphenyl benzoic acid (619-21-6) → 2-hydroxy-5-formylbenzoic acid (616-76-2)

Guidance literature:

With oxygen; potassium acetate; palladium diacetate; C₁₉H₂₄N₂O; p-benzoquinone; In N,N-dimethyl-formamide; at 110 ℃; for 24h; under 760.051 Torr; regioselective reaction;

DOI:10.1126/science.abg2362

Reference yield: 55.7%

hexamethylenetetramine (100-97-0) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 3-formylsalicylic acid (610-04-8) + 2-hydroxy-5-formylbenzoic acid (616-76-2)

Guidance literature:

hexamethylenetetramine; salicylic acid; With copper(I) oxide; In trifluoroacetic acid; for 5h; Reflux;

With hydrogenchloride; In water; at 20 ℃; for 1h; Concentration; Reagent/catalyst; regioselective reaction;

DOI:10.1007/s11164-014-1881-5

upstream raw materials:

hexamethylenetetramine

acetic acid

salicylic acid

4-hydroxyisophthalic acid

Downstream raw materials:

5-((2Ξ,4S)-3,4r-dimethyl-5c-phenyl-oxazolidin-2-yl)-2-hydroxy-benzoic acid

5-formyl-2-hydroxy-benzoic acid ethyl ester

C₂₆H₁₈O₁₀

5-[(E)-3-(5-Bromo-2,4-dihydroxy-phenyl)-3-oxo-propenyl]-2-hydroxy-benzoic acid

Refernces

• 1、 Li, Zhen,Wang, Zhen,Chekshin, Nikita,Qian, Shaoqun,Qiao, Jennifer X.,Cheng, Peter T.,Yeung, Kap-Sun,Ewing, William R.,Yu, Jin-Quan. "A tautomeric ligand enables directed C-H hydroxylation with molecular oxygen". . p. 1452 - 1457. Retrieved 2021/06/30.
• 2、 Plasch, Katharina,Resch, Verena,Hitce, Julien,Pop?oński, Jaros?aw,Faber, Kurt,Glueck, Silvia M.. "Regioselective Enzymatic Carboxylation of Bioactive (Poly)phenols". . p. 959 - 965. Retrieved 2017/03/27.