m-Phthalaldehyde
[CAS# 626-19-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic aldehyde (containing acetal, hemiacetal)
• Name: m-Phthalaldehyde
• Synonyms: Isophthalaldehyde; 1,3-Benzenedialdehyde
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• CAS Registry Number: 626-19-7
• EC Number: 210-935-8
• SMILES: C1=CC(=CC(=C1)C=O)C=O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 87-88 °C (Expl.)
• Index of Refraction: 1.623, Calc.^*
• Boiling Point: 255.3±23.0 °C (760 mmHg), Calc.^*, 281.1 °C (Expl.)
• Flash Point: 94.1±19.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

m-Phthalaldehyde, also known as 1,3-benzenedialdehyde, is an organic compound with the chemical formula C8H6O2. It is a member of the phthalaldehyde family, characterized by the presence of two aldehyde functional groups attached to a benzene ring at the 1 and 3 positions. m-Phthalaldehyde is a valuable compound in both synthetic organic chemistry and industrial applications.

The discovery of m-phthalaldehyde dates back to the late 19th century when phthalic acid and its derivatives were being explored for various chemical transformations. The compound itself was synthesized by the oxidation of m-xylene, a common precursor in the synthesis of phthalate compounds. Since then, m-phthalaldehyde has been investigated for its potential in diverse chemical reactions and industrial uses.

m-Phthalaldehyde is used primarily as an intermediate in the synthesis of other organic compounds. Its structure, with two reactive aldehyde groups, makes it an important building block for creating larger, more complex molecules. It is involved in the formation of imidazole and other heterocyclic compounds, which are valuable in pharmaceutical and agrochemical industries.

In addition to its role in synthetic chemistry, m-phthalaldehyde has been used as a reagent in chemical reactions such as condensation reactions and the synthesis of Schiff bases. The aldehyde groups are highly reactive and can form covalent bonds with amines and other nucleophiles, leading to the formation of useful derivatives. These reactions are widely applied in the preparation of polymeric materials, dyes, and other specialty chemicals.

Furthermore, m-phthalaldehyde is also a component in the production of certain resins and coatings, where it contributes to the material's properties. Its ability to undergo polymerization reactions makes it useful in the development of high-performance materials, such as those used in the electronics industry.

In conclusion, m-phthalaldehyde is an important chemical intermediate with applications in organic synthesis, the production of heterocyclic compounds, and materials science. Its chemical reactivity and role in the synthesis of complex molecules have made it a valuable substance in both industrial and academic research.

References

2020. Synthesis and Characterization of Aromatic Poly(azomethine ether)s with Different meta- and para-Phenylene Linkage Contents. Fibers and Polymers, 21(2).
DOI: 10.1007/s12221-020-9690-5

2023. Design, synthesis and antimicrobial activities of novel bis-Mannich bases derived from lawsone. Research on Chemical Intermediates, 49(11).
DOI: 10.1007/s11164-023-05103-6

2024. Imidazole as an organocatalyst for the rapid synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous medium. Journal of Chemical Sciences, 136(4).
DOI: 10.1007/s12039-024-02327-w