Acetone oxime
[CAS# 127-06-0]

Identification

• Classification: Organic raw materials >> Nitrogen-containing compound
• Name: Acetone oxime
• Synonyms: 2-Propanone oxime; Acetoxime
• Molecular Formula: C₃H₇NO
• Molecular Weight: 73.09
• CAS Registry Number: 127-06-0
• EC Number: 204-820-1
• SMILES: CC(=NO)C

Properties

• Density: 0.901
• Melting point: 58-62 °C
• Boiling point: 135 °C
• Flash point: 60 °C
• Water solubility: 330 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07;GHS09 Danger
• Risk Statements: H228-H302-H312-H317-H318-H351-H373
• Safety Statements: P203-P210-P240-P241-P260-P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P354+P338-P317-P318-P319-P321-P330-P333+P317-P362+P364-P370+P378-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H302
Flammable solids	Flam. Sol.	1	H228
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Flammable solids	Flam. Sol.	2	H228
Skin sensitization	Skin Sens.	1A	H317

Discovery and Applications

Acetone oxime is an important chemical compound with the chemical name 2-acetone oxime or oximeacetone, which was originally synthesized and characterized by the reaction of acetone and hydroxylamine. This simple synthesis produces a stable colorless solid or liquid, depending on the temperature, with a characteristic odor similar to that of acetone. Its molecular structure contains a ketoximine functional group (-C=NOH), which gives it unique chemical reactivity and application potential.

Acetone oxime is soluble in water and common organic solvents such as ethanol and acetone, facilitating its use in various formulations and chemical processes. Its physical state changes with temperature: at room temperature, it usually exists as a solid, while higher temperatures turn it into a liquid. The oxime functionality enables acetone oxime to undergo typical reactions of oximes, including condensation, hydrolysis, and complex formation with metal ions.

Acetone oxime is a valuable intermediate in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. It is capable of selective transformations, such as acylation and alkylation, and is a versatile precursor in organic synthesis.

Due to its ability to chelate metal ions and scavenge free radicals, acetone oxime is used as an antioxidant additive in a variety of industrial formulations, including paints, coatings, and polymeric materials. It is also used as a corrosion inhibitor in metalworking fluids and industrial cooling systems.

In polymer chemistry, acetone oxime is used as a chain terminator for the production of acrylic polymers and resins. Its reaction with acrylates and methacrylates helps control the polymerization process, ensuring the desired molecular weight and polymer properties.

Acetone oxime is a cornerstone in the synthesis of pharmaceutical compounds, particularly in the development of antimicrobial agents and pharmaceutical intermediates. Its versatile reactivity allows the introduction of functional groups that are critical to drug efficacy and specificity. In laboratory settings, acetone oxime is used as an analytical reagent, such as to detect and quantify certain metal ions and carbonyl compounds. Its selective complexing properties make it valuable in chemical analysis and environmental monitoring.

References

1884. Zur Erkennung der Aldehyde und Ketone. Zeitschrift fur analytische Chemie, 23(1).
DOI: 10.1007/bf01360373

2023. Recent development advances in bio-based powder coatings: a review. Journal of Coatings Technology and Research, 21(1).
DOI: 10.1007/s11998-023-00849-5

2024. Dynamic polymers based on oxime-urethane chemistry: design, performances, and applications. Science China Chemistry, 67(12).
DOI: 10.1007/s11426-024-2409-6