2'-Aminoacetophenone
[CAS# 551-93-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: 2'-Aminoacetophenone
• Synonyms: o-Aminoacetophenone; 1-(2-Aminophenyl)ethanone
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• CAS Registry Number: 551-93-9
• EC Number: 209-002-8
• SMILES: CC(=O)C1=CC=CC=C1N

Properties

• Density: 1.112
• Melting point: 20 °C
• Boiling point: 70-71 °C (3 torr)
• Refractive index: 1.6142-1.6162
• Flash point: 112 °C

Safety Data

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

Hazard Classification

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

Discovery and Applications

2'-Aminoacetophenone, also known as ortho-aminoacetophenone or o-aminoacetophenone, was first synthesized and characterized in the early 20th century as part of research into aromatic compounds and their derivatives. Chemists were exploring methods to modify the structure of acetophenone—a common aromatic ketone—to introduce functional groups with potential applications in various fields. Through synthetic routes involving the condensation of acetophenone with ammonia or amines, 2'-Aminoacetophenone was successfully produced. Its discovery represented a significant advancement in organic chemistry, providing a versatile building block for the synthesis of diverse organic compounds.

2'-Aminoacetophenone serves as a key intermediate in the synthesis of various pharmaceutical compounds, including analgesics, antipyretics, and antimicrobial agents. Its amino group allows for further functionalization to create structurally diverse molecules with desired biological activities. Researchers utilize 2'-Aminoacetophenone in medicinal chemistry to explore structure-activity relationships and develop new drug candidates. By modifying its chemical structure, they can optimize pharmacokinetic properties, enhance potency, and reduce toxicity, leading to the discovery of novel therapeutics for various diseases.

2'-Aminoacetophenone serves as a versatile building block in organic synthesis, allowing chemists to construct complex molecules with specific functionalities. Its aromatic ring and amino group enable diverse chemical transformations, such as nucleophilic substitution, oxidation, and reduction, facilitating the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. Chemists use 2'-Aminoacetophenone as a precursor for synthesizing heterocyclic compounds, including benzimidazoles, benzothiazoles, and benzoxazoles. These heterocycles are valuable intermediates in pharmaceutical and agrochemical synthesis, exhibiting a wide range of biological activities.

2'-Aminoacetophenone derivatives are investigated for their potential as catalysts in organic reactions. Functionalized derivatives containing additional functional groups, such as amine or hydroxyl groups, exhibit catalytic activity in various transformations, including oxidation, hydrogenation, and C-C bond formation. Chemists utilize 2'-Aminoacetophenone as a ligand in coordination chemistry to form metal complexes with transition metals. These complexes find applications as catalysts in organic reactions and as models for studying coordination chemistry and catalytic mechanisms.

2'-Aminoacetophenone is employed as an analytical reagent in chemical analysis techniques, including spectrophotometry and chromatography. Its characteristic absorption spectrum and reactivity with specific reagents enable qualitative and quantitative analysis of various compounds in complex mixtures. Derivatives of 2'-Aminoacetophenone are used as fluorescent probes in biochemical and biomedical research. They exhibit fluorescence properties upon binding to specific biomolecules, allowing for the detection and imaging of biological targets in cells and tissues.

References

2024. Sensory and chemical profiling of boar taint compounds. Meat Science, 211.
DOI: 10.1016/j.meatsci.2024.109497

2023. 2-Aminoacetophenone mediates Pseudomonas aeruginosa persistence via epigenetic regulation. mBio, 14(3).
DOI: 10.1128/mbio.00159-23

2022. Activated carbon-agarose film for mitigation of 2-aminoacetophenone malodor. Journal of Materials Science, 57(33).
DOI: 10.1007/s10853-022-07598-7