Phthalaldehyde


o-Phthalaldehyde or ortho-phthalaldehyde is the chemical compound with the formula C6H42. Often abbreviated OPA, the molecule is a dialdehyde, consisting of two formyl groups attached to adjacent carbon centres on a benzene ring. This pale yellow solid is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids. OPA dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air.

Synthesis and reactions

The compound was first described in 1887 when it was prepared from α,α,α’,α’-tetrachloro-ortho-xylene. A more modern synthesis is similar: the hydrolysis of the related tetrabromoxylene using potassium oxalate, followed by purification by steam distillation.
The reactivity of OPA is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4 and C6H42O, respectively. Its reactions with nucleophiles often involves the reaction of both carbonyl groups.

Biochemistry

OPA is used in a very sensitive fluorescent reagent for assaying amines or sulfhydryls in solution, notably contained in proteins, peptides, and amino acids, by capillary electrophoresis and chromatography. OPA reacts specifically with primary amines above their isoelectric point Pi in presence of thiols. OPA reacts also with thiols in presence of an amine such as n-propylamine or 2-aminoethanol. The method is spectrometric with excitation at 330-390 nm ).

Disinfection

OPA is commonly used as a high-level disinfectant for medical instruments, commonly sold under the brand names of Cidex OPA or TD-8. Disinfection with OPA is indicated for semi-critical instruments that come into contact with mucous membranes or broken skin, such as specula, laryngeal mirrors, and internal ultrasound probes.

Poly(phthalaldehyde)

OPA can be polymerized. In the polymer, one of the oxygen atoms forms a bridge to the other non-ring carbon of the same phthalaldehyde unit, while the other bridges to a non-ring carbon of another phthalaldehyde unit. Poly is used in making a photoresist.

In winemaking

The Nitrogen by O-Phthaldialdehyde Assay is one of the methods used in winemaking to measure yeast assimilable nitrogen needed by wine yeast in order to successfully complete fermentation.

Isomeric phthalaldehydes

Related to ortho-phthalaldehyde are the meta- and para-isomers, which are respectively named isophthalaldehyde and terephthalaldehyde.