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2-Carboxybenzaldehyde is a carboxylated derivative of benzaldehyde which is readily converted to 2-hydroxymethyl benzoic acid by CBA dehydrogenase. 2-Carboxybenzaldehyde is a metabolite of ampicillin phthalidyl ester. It has been used to synthesize a series of N-substituted isoindolinones by reductive C-N coupling and intramolecular amidation with amines.
Ka young lee; Jeong mi kim; Jae nyoung kim. Facile synthesis of 3-alkylidene-3H-isobenzofuranones from the Baylis-Hillman reaction of 2-carboxybenzaldehyde. Synlett. 2003, 357-360.
KA Krasnov; VG Kartsev; EE Santarovich. Reaction of Barbituric, 2-Thiobarbituric Acids and Their Derivatives with 2-Carboxybenzaldehyde and Opianic Acid: Synthesis and Tautomerism of 5-(3'-Oxo-1',3'-dihydroisobenzofuran-1'-yl)barbituric Acids and Their 2-Thio Analogs. Chemistry of Heterocyclic Compounds. 2002, 38, 702-709.
The aldehyde is in equilibrium with the cyclic lactol, which reacts with both alkyl and aryl Grignard reagents to give substituted phthalides: Tetrahedron, 44, 2903 (1988):
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant