60759-49-1

Basic information

• Product Name: 3-Acetyl-2(3H)-oxazolone
• Synonyms: 3-Acetyl-2(3H)-oxazolone;3-Acetyloxazol-2(3H)-one
• CAS NO: 60759-49-1
• Molecular Formula: C₅H₅NO₃
• Molecular Weight: 127.0981
• Mol File: 60759-49-1.mol

Chemical Properties

• Melting Point: 36-38 °C
• Boiling Point: 214.6 °C at 760 mmHg
• Flash Point: 107.2 °C
• Appearance: /
• Density: 1.383 g/cm³
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.52
• PKA: -3.04±0.20(Predicted)
• CAS DataBase Reference: 3-Acetyl-2(3H)-oxazolone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-2(3H)-oxazolone(60759-49-1)
• EPA Substance Registry System: 3-Acetyl-2(3H)-oxazolone(60759-49-1)

Safety Data

• Hazardous Substances Data: 60759-49-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Acetyl-2(3H)-oxazolone is used as a key building block for the synthesis of various pharmaceutical products. Its chemical versatility allows for the creation of a wide range of biologically active compounds, making it an essential component in drug discovery and development.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Acetyl-2(3H)-oxazolone serves as a crucial intermediate in the synthesis of agrochemicals. Its ability to form various chemical reactions enables the production of effective compounds for crop protection and other agricultural applications.
Used in Organic Synthesis:
3-Acetyl-2(3H)-oxazolone is utilized as a versatile reagent in organic synthesis. Its unique structure and properties facilitate a variety of chemical reactions, such as acylation and nucleophilic addition, making it an indispensable tool for chemists in the synthesis of complex organic molecules.
Used in Amino Acid Formation:
As an intermediate in the formation of amino acids, 3-Acetyl-2(3H)-oxazolone plays a significant role in the development of essential building blocks for proteins and other biologically important molecules. Its involvement in this process highlights its importance in the broader field of biochemistry and molecular biology.

InChI:InChI=1/C5H5NO3/c1-4(7)6-2-3-9-5(6)8/h2-3H,1H3

Upstream product

• 60759-48-0 N-acetyl-5-chloro-2-oxazolidinone 
• 14441-94-2 4-methoxy-1,3-oxazolidin-2-one 
• 108-24-7 acetic anhydride 
• 78605-38-6 Diphenyl 2-oxo-3-oxazolinylphosphonate 
• 64-19-7 acetic acid 
• 1432-43-5 3-acetyl-1,3-oxazolidin-2-one 

Downstream Products

• 121348-86-5 (2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate 
• 103-84-4 Acetanilid 
• 32362-99-5 benzylthioacetate 
• 614-80-2 2-(acetylamino)phenol 
• 29823-47-0 N-benzyl-N-methylacetamide 
• 27584-70-9 4-oxazolin-2-one 
• 68235-19-8 4-acetyl-2-oxa-4-aza-bicyclo[3.2.0]heptan-3-one 
• 140-11-4 Benzyl acetate 
• 127541-99-5 C₁₃H₁₁NO₄ 
• 880-52-4 N-(1-adamantyl)acetamide 
• 1743-60-8 17-β-estradiol 17-acetate 
• 103-45-7 acetic acid phenethyl ester 
• 58556-55-1 2-(4-hydroxyphenyl)ethyl acetate 
• 60037-42-5 2-(4-acetoxyphenyl)ethyl acetate 

Relevant articles and documents

OXATHIAZINE DERIVATIVES SUBSTITUTED WITH CARBOCYCLES OR HETEROCYCLES, METHOD FOR PRODUCING SAME, DRUGS CONTAINING SAID COMPOUNDS, AND USE THEREOF

The invention relates to the compounds of formula (I) and physiologically acceptable salts thereof. The compounds are suitable, e.g., for treating hyperglycemia.

2-Dienylphenacyloxazolones and an intramolecular Diels-Alder approach to the A-B-C ring system of phenanthridone alkaloids

A general route to the A-B-C ring system of phenanthridone alkaloids is available by acylation of 2-oxa-zolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels-Alder reaction and hydrolysis.

A dichlorination-reductive-dechlorination route to N-acetyl-2-oxazolone

We have shown that sulfuryl chloride is an efficient reagent for the conversion of 2-oxazolidinone into the dichloro derivative, N-acetyl-4,5- dichloro-2-oxazolidinone. Subsequent Zn/AcOH reductive dehalogenation of this trans-dichloride gives N-acetyl-2-oxazolone. The dichloride was previously reported as an undesired side product in the preparation of N-acetyl-2-oxazolone from the monochloro oxazolidinone. In our hands, the dichloride is a key intermediate in a new synthesis of 2-oxazolone, that avoids the use of chlorine gas. Georg Thieme Verlag Stuttgart.

A CONVENIENT PREPARATION OF 3H-1,3-OXAZOL-2-ONE AND ITS N-FORMYL DERIVATIVE

The electrochemical hydroxylation of 1,3-oxazolidin-2-one to 4-hydroxy-1,3-oxazolidin-2-one is reported; a substantial size product is the symmetrical ether derived from the hydroxycompound.An improved synthesis of 3H-1,3-oxazol-2-one has been developed; nothing more is involved than boiling the readily available 4-methoxy-1,3-oxazolidin-2-one with an excess of acetic acid and one equivalent of acetic anhydride, evaporation of the solvents and recrystallization of the residue.The mechanism of the reaction is discussed.In a reinvestigation of the known conversion, by acetic anhydride, of 4-methoxy-1,3-oxazolidin-2-one to N-acetyl-1,3-oxazol-2-one, we have uncovered the formation of two 3,4'-bioxazole side products , especially in the presence of added acids.We have found that N-formyl-1,3-oxazol-2-one can be made in good yield by treatment of 3H-1,3-oxazol-2-one with a mixture of formic acid and acetic anhydride ("acetic formic anhydride") in the presence of 4-(N,N-dimethylamino)pyridine; the formation of an intermediate phosphonate derived from 3H-1,3-oxazol-2-one, as described in the literature synthesis of N-formyl-1,3-oxazolone, is superfluous.

A NEW SYNTHESIS OF 2-OXAZOLONES

2-oxazolones were synthesized from 2-oxazolidinones utilizing anodic oxidation as the key step.

Highly Stereo- and Regioselective Formation of 2-Oxazolone Telomers, Potential Synthetic Intermediates for Amino Sugars

Free radical initiated reaction of 3-acyl-2-oxazolones proceeds smoothly in polyhalomethanes, which function as telogens, to give type 3 telomers of synthetic potential with high regio- and stereoselectivity, while the 3-alkyl derivatives failed to give such polyfunctional products.This particular telomerization can be controlled exclusively in the trans ''head-to-tail'' addition mode, as elucidated by 1H and 13C NMR and X-ray analysis of the products.Thus, the 3-benzoyl heterocycle 7 gave trans-4-chloro-5-(trichloromethyl)-2-oxazolidone (8) as a sole 1:1 adduct andtwo trans isomers of 4'-chloro-5-(trichloromethyl)-2,2'-dione (9a,b) as 2:1 telomers.Some characteristic reactions of the telomers are described.

A NEW REAGENT FOR ACTIVATING CARBOXYL GROUPS: DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE

Diphenyl 2-oxo-3-oxazolinylphosphonate serves as a carboxyl-activating reagent to permit a direct preparation of versatile intermediate, 3-acyl-2-oxazolones or a one-step formation of amides from carboxylic acids.