1,4-Phthalaldehyde
[CAS# 623-27-8]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 1,4-Phthalaldehyde
• Synonyms: 1,4-Benzenedicarboxaldehyde; Terephthaldicarboxaldehyde; Terephthalaldehyde; p-Phthalaldehyde
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• CAS Registry Number: 623-27-8
• EC Number: 210-784-8
• SMILES: C1=CC(=CC=C1C=O)C=O

Properties

• Melting point: 114-116 °C
• Boiling point: 245-248 °C
• Flash point: 76 °C
• Water solubility: 3 g/L (50 °C)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H311-H312-H315-H319-H331-H335
• Safety Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,4-Phthalaldehyde, also known as terephthalaldehyde, is an organic compound with the formula C8H6O2. It was first synthesized in the early 20th century. This compound is characterized by the presence of two aldehyde groups attached to a benzene ring in the para positions.

1,4-Phthalaldehyde is used as an intermediate in organic synthesis. Its two aldehyde groups make it a valuable building block for the preparation of more complex molecules. It can undergo various reactions, including condensation, reduction, and cyclization.

In pharmaceuticals, 1,4-phthalaldehyde is used to synthesize active pharmaceutical ingredients (APIs) and intermediates. Its reactivity makes it suitable for the formation of drugs that require aromatic aldehyde functionality. For example, it can be used in the synthesis of certain antibiotics and antiviral agents.

1,4-Phthalaldehyde is employed in the development of advanced materials. It is used in the production of polymers and resins, where its aromatic structure imparts stability and rigidity to the resulting materials. These materials are used in applications such as coatings, adhesives, and electronic components, where durability and performance are critical. Additionally, 1,4-phthalaldehyde is explored for its potential in creating photoresists and other materials used in the electronics industry.

In analytical chemistry, 1,4-phthalaldehyde is used as a reagent for the detection and quantification of various compounds. It is particularly useful in the determination of amines and amino acids. When reacted with these substances, it forms highly fluorescent derivatives, which can be easily detected and measured using fluorescence spectroscopy.

1,4-Phthalaldehyde is also used in biological research for the study of protein and enzyme interactions. Its ability to form cross-links with amino groups in proteins makes it useful in investigating protein structure and function.

In industry, 1,4-phthalaldehyde is used in the production of dyes and pigments. Its reactivity with various compounds allows for the synthesis of colorants with specific properties required for textiles, inks, and coatings. The compound's stability and reactivity make it an essential ingredient in the formulation of high-performance dyes and pigments.

References

2024. Optimizing photocatalytic activity for chromium reduction: the role of MgAl LDH/ triazine covalent organic framework /CdS nanocomposite. Emergent Materials.
DOI: 10.1007/s42247-024-00833-8

2024. Recent advances in the synthesis of dihydropyrimidinones via biginelli reaction. Journal of the Iranian Chemical Society.
DOI: 10.1007/s13738-024-03100-z

2024. Imine-containing Self-healing Waterborne Polyurethane Elastomeric Coating Derived from Bio-based Polyester Polyol. Journal of Polymers and the Environment.
DOI: 10.1007/s10924-024-03435-x