Phthalaldehyde
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| Phthalaldehyde | |
|---|---|
| Image:OPA.png | |
| Image:O-Phthalaldehyde 3D.png | |
| IUPAC name | o-Phthalaldehyde |
| Other names | o-Phthalic dicarboxaldehyde Benzene-1,2-dicarboxaldehyde Phthaldialdehyde |
| Identifiers | |
| CAS number | |
| RTECS number | TH6950000 |
| Properties | |
| Molecular formula | C8H6O2 |
| Molar mass | 134.13 g/mol |
| Appearance | yellow solid |
| Melting point |
55.5–56 °C |
| Solubility | organic solvents |
| Hazards | |
| R-phrases | 36/37/38 |
| S-phrases | 26-28-36 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
o-Phthalaldehyde is the chemical compound with the formula C6H4(CHO)2. Often abbreviated OPA, the molecule is a dialdehyde, consisting of two formyl (CHO) 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.
Contents |
Synthesis
The molecule was first described in 1887 when it was prepared from α,α,α',α’-tetrachloro-ortho-xylene.[1] A more modern synthesis is similar: the hydrolysis of the related tetrabromoxylene using potassium oxalate, followed by purification by steam distillation.[1] The reactivity of OPA is complicated by the fact that with water it forms both a mono- and dihydrate, C6H4(CHO)(CH2OH) and C6H4(CH2OH)2, respectively.[1]
Isomeric phthalaldehydes
Related to o-phthalaldehyde are the meta and para isomers, which are respectively named isophthalaldehyde (m.p. 87-88 °C, CAS# 626-19-7) terephthalaldehyde (m.p. 114-116 °C, CAS# 623-27-8).
References
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
