3-AMINO-2-OXAZOLIDINONE Chemical Properties

Melting point:

65-67 °C

Boiling point:

135 °C(Press: 0.7 Torr)

Density 

1.179

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.24±0.20(Predicted)

color 

White to Off-White

BRN 

109430

InChI

InChI=1S/C3H6N2O2/c4-5-1-2-7-3(5)6/h1-2,4H2

InChIKey

KYCJNIUHWNJNCT-UHFFFAOYSA-N

SMILES

O1CCN(N)C1=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

29349990

3-AMINO-2-OXAZOLIDINONE Usage And Synthesis

Chemical Properties

White Solid

Uses

A metabolite of Furazolidone and Nitrofuran. Environmental contaminants; Food contaminants; Heat processing contaminants

Definition

ChEBI: 3-Amino-2-oxazolidone is an oxazolidinone.

Synthesis

General procedure for the synthesis of 3-aminooxazolidin-2-one from 2-hydrazinoethanol and diethyl carbonate: 15.2 g (0.2 mol) of 2-hydrazinoethanol (Intermediate 1), 31.0 g (0.2 mol) of diethyl carbonate, and 3.0 g (57 mmol) of sodium methanol were added to a 100 mL three-necked flask, and the mixture was heated and refluxed for 4 hours. Upon completion of the reaction, the reaction mixture was cooled and a solid was precipitated. The solid was collected by vacuum filtration and dried. The solvent in the mother liquor was removed by distillation. The crude product was purified by column chromatography (eluent: methanol/dichloromethane, 1:20, v/v), and the resulting white solid was recrystallized in ethanol to give 15.3 g of 3-aminooxazolidin-2-one (Intermediate 2) in 75% yield. The product was characterized as follows: 1H-NMR (400 MHz, D2O) δ ppm: 4.33 (2H, t, J = 8.0 Hz), 3.94 (2H, s), 3.70 (2H, t, J = 4.0 Hz); EI-MS (m/z): 103.1 [M + H]+; Melting point: 64-66 °C.

References

[1] Patent: EP2952509, 2015, A1. Location in patent: Paragraph 0043; 0044
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 2277,2280, 2281
[3] Journal of the American Chemical Society, 1977, vol. 99, p. 1172 - 1180
[4] Journal of the Chemical Society, 1963, p. 3523 - 3528
[5] Journal of Organic Chemistry, 1966, vol. 31, p. 631 - 632

3-AMINO-2-OXAZOLIDINONE(80-65-9)Related Product Information

• 2-NP-AOZ
• Moxnidazole
• 3-AMINO-2-OXAZOLIDINONE
• 5-(4-morpholinmethyl)-3-amino-2-oxazolidinone
• Morphlinomethyl-3-[(5-nitrofurfurylidene)-amino]-2-oxazolidinone
• 5-((methylthio)methyl)-3-((5-nitrofurfurylidine)amino)-2-oxazolidinon
• 5-morpholinomethyl-3-(5-nitro-2-furfurylidine-amino)-2-oxazolidinon
• 3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone,3-[[(5-nitro-2-furanyl)methylene]amino]-2-Oxazolidinon
• Famoxadone
• Oxadixyl
• (+)-4-Amino-3-oxazolidinone
• 5-(Diallylaminomethyl)-3-[(5-nitrofurfurylidene)amino]-2-oxazolidinone
• 3-AMINO-2-OXAZOLIDINONE SULFATE
• 5-MORPHOLINOMETHYL-3-[5-NITROFURFURYLIDENEAMINO]-2-OXAZOLIDINONE TARTRATE SALT
• 2-NP-AOZ-D4
• 5-(4-Morpholinylmethyl-d8)-3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone
• 5-(4-Ethyl-1-piperazinyl)methyl-3-(5-nitrofurfurylidene)amino-2-oxazolidinone
• 3-AMINO-2-OXAZOLIDINONE D4