Isatoic anhydride
[CAS# 118-48-9]

Identification

• Classification: Biochemical >> Biochemical reagent >> Biological dye
• Name: Isatoic anhydride
• Synonyms: 1,2-Dihydro-4H-3,1-benzoxazine-2,4-dione; 4H-3,1-Benzoxazine-2,4(1H)-dione
• Molecular Formula: C₈H₅NO₃
• Molecular Weight: 163.13
• CAS Registry Number: 118-48-9
• EC Number: 204-255-0
• SMILES: C1=CC=C2C(=C1)C(=O)OC(=O)N2

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.52 g/mL (Expl.)
• Melting point: 233 °C (Expl.)
• Index of Refraction: 1.586, Calc.^*
• Flash point: 308 °C (Expl.)
• Water solubility: decomposes

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319-H317
• Safety Statements: P261-P264+P265-P272-P280-P302+P352-P305+P351+P338-P321-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H320

Discovery and Applications

Isatoic anhydride, also known as 2-phthalimidic anhydride, is an organic compound with the molecular formula C8H5NO3. It is a white crystalline solid that is primarily used as an intermediate in organic synthesis. The compound is derived from phthalic anhydride and is known for its utility in the preparation of various pharmaceutical and chemical products.

The discovery of isatoic anhydride can be traced to the early studies of phthalic acid derivatives, which are important in the chemical industry. Phthalic anhydride, a key starting material in the production of a wide variety of chemicals, reacts with ammonia or primary amines to form isatoic anhydride. This compound has an imide group attached to the benzene ring, which contributes to its chemical reactivity and stability.

Isatoic anhydride is widely employed in the synthesis of heterocyclic compounds, particularly those with biological activity. It serves as a precursor for the preparation of isatoic acid derivatives, which are important in the production of pharmaceuticals, dyes, and agrochemicals. One of the notable applications of isatoic anhydride is in the synthesis of quinazoline derivatives, which exhibit various pharmacological properties, including anticancer and antimicrobial activities. The compound’s ability to form stable imide structures makes it an ideal building block for creating bioactive molecules.

Additionally, isatoic anhydride is used in the synthesis of various dyestuffs and pigments. The compound’s reactivity with amines allows for the production of a range of colored compounds, which are utilized in textile and coating industries. It is also used in the preparation of certain specialty polymers, where it can participate in polymerization reactions or serve as a crosslinking agent.

In summary, isatoic anhydride is an important chemical intermediate with significant applications in the pharmaceutical, dye, and polymer industries. Its ability to form reactive derivatives makes it a valuable compound in the synthesis of bioactive molecules and specialty chemicals.

References

2024. A brief review on imidazole, triazine, and isatin derivatives: synthesis approaches and their applications. Discover Chemistry.
DOI: 10.1007/s44371-024-00057-z

2023. Modification of Hydroxysodalite Nanoparticles by (3-aminopropyl)trimethoxysilane and Isatoic Anhydride as a Novel Composite for Efficient Sorption of Cu(II) Ions from Aqueous Media. Silicon.
DOI: 10.1007/s12633-023-02743-6

2022. Phenylbenzohydrazides Obtained from Isatoic Anhydride Present Anti-Inflammatory Activity In Vivo and In Vitro. Biomolecules.
DOI: 10.3390/biom12121901