3-Acetamidophthalic anhydride
[CAS# 6296-53-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: 3-Acetamidophthalic anhydride
• Synonyms: 3-Acetylaminophthalic anhydride; NSC 16261; NSC 17048
• Molecular Formula: C₁₀H₇NO₄
• Molecular Weight: 205.17
• CAS Registry Number: 6296-53-3
• EC Number: 808-040-8
• SMILES: CC(=O)NC1=CC=CC2=C1C(=O)OC2=O

Properties

• Solubility: Slightly soluble (1.2 g/L) (25 °C), Calc.^*
• Density: 1.512±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 185-186 °C^**
• Index of Refraction: 1.658, Calc.^*
• Boiling Point: 489.1±28.0 °C (760 mmHg), Calc.^*
• Flash Point: 249.6±24.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Bogert, Marston Taylor

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

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
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

3-Acetamidophthalic anhydride is an important organic compound primarily used in the synthesis of various pharmaceuticals, agrochemicals, and polymers. This compound belongs to the class of phthalic anhydrides, which are cyclic dicarboxylic acid derivatives. The discovery of 3-acetamidophthalic anhydride can be traced back to the exploration of phthalic anhydrides in the early 20th century, where chemists were investigating their reactivity and potential applications. The introduction of an acetamido group into the phthalic anhydride framework enhances its chemical properties, making it a valuable intermediate in synthetic organic chemistry.

The structure of 3-acetamidophthalic anhydride consists of a phthalic anhydride core with an acetamido substituent at the 3-position. This modification imparts unique reactivity characteristics to the compound, particularly its ability to undergo nucleophilic attack due to the electron-withdrawing nature of the acetamido group. As a result, 3-acetamidophthalic anhydride serves as a versatile building block for synthesizing various complex organic molecules.

One of the primary applications of 3-acetamidophthalic anhydride lies in the pharmaceutical industry, where it is used as an intermediate in the synthesis of bioactive compounds. For instance, it can be involved in the production of non-steroidal anti-inflammatory drugs (NSAIDs) and other therapeutic agents. The incorporation of the acetamido group enhances the lipophilicity and bioavailability of the resulting drugs, improving their efficacy and pharmacokinetic properties.

Moreover, 3-acetamidophthalic anhydride has applications in the production of agrochemicals, where it is utilized to develop herbicides and pesticides. The ability to modify chemical structures through the introduction of the acetamido moiety allows for the optimization of these compounds, enhancing their selectivity and potency against target organisms. The use of 3-acetamidophthalic anhydride in agrochemical synthesis contributes to the development of safer and more effective agricultural products.

In addition to its applications in pharmaceuticals and agrochemicals, 3-acetamidophthalic anhydride is also valuable in the polymer industry. It can be used to synthesize polyamide resins and other polymers, where its anhydride functionality plays a crucial role in forming cross-linked structures. The resulting polymers exhibit improved mechanical properties and thermal stability, making them suitable for various industrial applications.

Research continues to explore the potential of 3-acetamidophthalic anhydride in other fields, including material science and nanotechnology. The compound's unique reactivity and versatility make it a promising candidate for the development of new materials with tailored properties.

In summary, 3-acetamidophthalic anhydride is a significant compound in organic synthesis, with wide-ranging applications in pharmaceuticals, agrochemicals, and polymers. Its unique structure and reactivity facilitate the development of bioactive compounds and advanced materials, highlighting its importance in various chemical industries.

References

2015. Apremilast. Pharmaceutical Substances.
URL: KD-01-0207