29218-21-1

Basic information

• Product Name: 3-Phenyl-5-(hydroxymethyl)oxazolidine-2-one
• Synonyms: 3-Phenyl-5-(hydroxymethyl)oxazolidine-2-one;5-(Hydroxymethyl)-3-phenyl-2-oxazolidinone;5-(hydroxymethyl)-3-phenyloxazolidin-2-one;2-Oxazolidinone, 5-(hydroxymethyl)-3-phenyl-
• CAS NO: 29218-21-1
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.1992
• Mol File: 29218-21-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 326.4°Cat760mmHg
• Flash Point: 151.2°C
• Appearance: /
• Density: 1.287g/cm³
• Vapor Pressure: 8.8E-05mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 3-Phenyl-5-(hydroxymethyl)oxazolidine-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-5-(hydroxymethyl)oxazolidine-2-one(29218-21-1)
• EPA Substance Registry System: 3-Phenyl-5-(hydroxymethyl)oxazolidine-2-one(29218-21-1)

Safety Data

• Hazardous Substances Data: 29218-21-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11NO3/c12-7-9-6-11(10(13)14-9)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2

Upstream product

• 141-97-9 ethyl acetoacetate 
• 556-52-5 oxiranyl-methanol 
• 62-53-3 aniline 
• 616-38-6 carbonic acid dimethyl ester 
• 105-58-8 Diethyl carbonate 
• 584-08-7 potassium carbonate 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 10525-86-7 N-(2-oxiranylmethyl)aniline 
• 124-38-9 carbon dioxide 
• 76226-32-9 N-(3-chloro-2-hydroxypropyl)aniline 
• 5840-15-3 1-phenylamino 2,3-propanediol 
• 103-71-9 phenyl isocyanate 
• 947233-24-1 5-[(benzyloxy)methyl]-3-phenyl-1,3-oxazolidin-2-one 
• 64589-90-8 l-5-(hydroxymethyl)-3-[4-(methylthio)phenyl]-2-oxazolidinone 

Downstream Products

• 37072-61-0 5-acetoxymethyl-3-phenyl-oxazolidin-2-one 
• 87472-10-4 l-4-[5-(hydroxymethyl)-2-oxooxazolidin-3-yl]-benzenesulfonamide 
• 87472-09-1 dl-4-[5-(trifluoroacetoxymethyl)-2-oxooxazolidin-3-yl]benzenesulfonyl chloride 
• 350850-72-5 1-[(4-Cyano-5-methyl-4-phenyl)hexyl]-4-[(3-phenyl-2-oxo-5-oxazolidinyl)methyl]piperazine 
• 5255-96-9 5-[(4-tert-butylphenoxy)methyl]-3-phenyl-1,3-oxazolidin-2-one 
• 1228455-10-4 C₁₈H₁₈N₂O₄ 
• 1228454-94-1 C₁₇H₁₆N₂O₄ 
• 1174337-90-6 5-[(3-aminophenoxy)methyl]-3-phenyl-1,3-oxazolidin-2-one 
• 1228454-95-2 C₁₈H₁₈N₂O₄ 
• 1228454-93-0 C₁₆H₁₆N₂O₃ 
• 1228454-91-8 C₁₇H₁₇NO₄ 
• 1174337-66-6 5-((4-methoxyphenoxy)methyl)-3-phenyloxazolin-2-one 
• 5255-94-7 5-(4-chloro-phenoxymethyl)-3-phenyl-oxazolidin-2-one 
• 5255-97-0 3-phenyl-5-o-tolyloxymethyl-oxazolidin-2-one 

Relevant articles and documents

Discovery of oxazolidinone-based heterocycles as subtype selective sigma-2 ligands

The sigma-2 (σ2) receptor, also known as the Transmembrane Protein 97 (TMEM97, and MAC30 (Meningioma-associated protein), has been linked to a number of conditions are disease states such as schizophrenia, cancer, Alzheimer’s disease, traumatic brain injury, and neuropathic pain. As part or our on-going effort identify novel σ2 ligands, we have identified a series of novel, functionalized oxazolidin-2-one sigma-2 ligands (4). Our lead compound (4h) demonstrated high affinity (Ki = 36 nM) and excellent σ1/σ2 selectivity (79-fold). Evaluation of its affinity at key CNS targets via the Psychoactive Drug Screening Program (PDSP) also indicated a high degree of selectivity for σ2 over other receptors. [Figure not available: see fulltext.].

Switchable synthesis of cyclic carbamates by carbon dioxide fixation at atmospheric pressure

The base-promoted switchable synthesis of five- and six-membered cyclic carbamates using atmospheric pressure carbon dioxide as the C1 source was developed. The chemoselectivity of products was simply controlled by changing bases and solvents. The reaction proceeds effectively under mild conditions, affording valuable cyclic carbamates. Experimental results and DFT studies revealed the reaction mechanism.

Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.