27353-93-1

Basic information

• Product Name: 5-{4-nitrophenyl}-1,3-oxazol-2(3H)-one
• Synonyms: 5-{4-nitrophenyl}-1,3-oxazol-2(3H)-one
• CAS NO: 27353-93-1
• Molecular Formula: C₉H₆N₂O₄
• Molecular Weight: 206.15494
• Mol File: 27353-93-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-{4-nitrophenyl}-1,3-oxazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-{4-nitrophenyl}-1,3-oxazol-2(3H)-one(27353-93-1)
• EPA Substance Registry System: 5-{4-nitrophenyl}-1,3-oxazol-2(3H)-one(27353-93-1)

Safety Data

• Hazardous Substances Data: 27353-93-1(Hazardous Substances Data)

Upstream product

• 99-81-0 4-Nitrophenacyl bromide 
• 88419-04-9 3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione 
• 89848-67-9 Sodium; (2S,3R)-3-(4-nitro-phenyl)-oxirane-2-carboxylate 
• 89848-80-6 (2S,3R)-3-(4-Nitro-phenyl)-oxirane-2-carbonyl chloride 
• 89848-93-1 (2S,3R)-3-(4-Nitro-phenyl)-oxirane-2-carbonyl azide 

Relevant articles and documents

Substituted Oxopyridine Derivatives and Use Thereof in the Treatment of Cardiovascular Disorders

The invention relates to substituted oxopyridine derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and oedemas, and also ophthalmic disorders.

Synthesis of α,β-Epoxyacyl Azides and Their Rearrangement to Epoxy Isocyanates and 3- and 4-Oxazolin-2-ones

The conversion of α,β-epoxy carboxylates 6 into α,β-epoxyacyl azides 4 proceeds either via reaction of the mixed anhydrides 7 with sodium azide or via reaction of epoxyacyl chlorides 8 with hydrazoic acid-pyridine.The latter method is preferred.The azides 4 undergo a smooth thermal Curtius rearrangement to give 4-oxazolin-2-ones 10 for the substrates 4a-h having a hydrogen atom at C(β).Monitoring this reaction by means of IR shows that the epoxy isocyanates 5 are intermediates.Intramolecular ring expansion of 5 then leads to 3-oxazolin-2-ones 9 that tautomerizeto the 4-isomers 10a-h.Epoxyacyl azides 4i,n-q, having no hydrogen atom at C(β), producing 3-oxazolin-2-ones 9i,n-q by a proton shift is not possible.The products 9i and 9q rapidly add water at the imine bond to give oxazolidin-2-ones 11.Epoxy isocyanate 5k is reasonable stable in solution; reaction with methanol affords urethane 12.