| Identification | More | [Name]
5-Formylsalicylic acid | [CAS]
616-76-2 | [Synonyms]
2-HYDROXY-5-FORMYLBENZOIC ACID
5-FORMYL-2-HYDROXYBENZOIC ACID
5-FORMYLSALICYLIC ACID
5-FORMYLSALICYLIC ACID 97%
3-Carboxy-4-hydroxybenzaldehyde
6-Hydroxyisophthalaldehydic acid
5-Formylsalicylic acid ,98% | [EINECS(EC#)]
210-492-0 | [Molecular Formula]
C8H6O4 | [MDL Number]
MFCD00006945 | [Molecular Weight]
166.13 | [MOL File]
616-76-2.mol |
| Chemical Properties | Back Directory | [Appearance]
light beige fine crystalline powder | [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. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
powder
| [pka]
2.67±0.10(Predicted) | [color ]
brownish-yellow
| [Detection Methods]
HPLC,NMR | [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 Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29189900 |
| Hazard Information | Back Directory | [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 |
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