2-Phenylacetamide
[CAS# 103-81-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 2-Phenylacetamide
• Synonyms: alpha-Phenylacetamide
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.17
• CAS Registry Number: 103-81-1
• EC Number: 203-147-0
• SMILES: C1=CC=C(C=C1)CC(=O)N

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 156 °C (Expl.)
• Index of Refraction: 1.553, Calc.^*
• Boiling Point: 312.2±21.0 °C (760 mmHg), Calc.^*
• Flash Point: 142.6±22.1 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

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

Discovery and Applications

2-Phenylacetamide is an organic compound with the molecular formula C₈H₉NO. It is a white crystalline solid that is sparingly soluble in water but more soluble in organic solvents such as ethanol and acetone. The compound is structurally related to acetanilide and benzamide, possessing both an amide functional group and a phenyl substituent. It has been synthesized through various established methods, including the reaction of phenylacetic acid with ammonia or amine derivatives under controlled conditions.

2-Phenylacetamide has been utilized in pharmaceutical and chemical research as an intermediate in the synthesis of biologically active compounds. Due to its structural similarity to certain bioactive molecules, it has served as a precursor in the development of pharmaceutical agents, particularly in analgesic and anticonvulsant drug research. Its role in medicinal chemistry has been documented, and its derivatives have been investigated for potential pharmacological applications.

In organic synthesis, 2-Phenylacetamide has been employed as a starting material or intermediate for the production of more complex molecules. It has been used in the preparation of heterocyclic compounds and in various reactions involving amide functionality, such as hydrolysis, reduction, and condensation reactions.

The compound has also been explored in agrochemical applications, where it has contributed to the synthesis of plant growth regulators and other biologically relevant molecules. Its involvement in the preparation of fine chemicals and specialty materials highlights its importance in chemical manufacturing.

Beyond its applications in synthetic chemistry and pharmaceuticals, 2-Phenylacetamide has been studied for its physicochemical properties, including its thermal stability and reactivity. The compound’s crystalline structure and melting behavior have been analyzed in material science contexts to better understand its intermolecular interactions and potential applications in solid-state chemistry.

Due to its established chemical properties and role in synthesis, 2-Phenylacetamide remains a compound of interest in both research and industrial applications. Its utility as a versatile intermediate in chemical and pharmaceutical manufacturing underscores its significance in applied chemistry.

References

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DOI: 10.1186/s12896-024-00920-y

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2024. Chemical Constituents from the Seeds of Sinapis alba. Chemistry of Natural Compounds, 60(4).
DOI: 10.1007/s10600-024-04434-z