16285-78-2

Basic information

• Product Name: 2,3-diphenyl-1,3-oxazolidine
• CAS NO: 16285-78-2
• Molecular Formula: C₁₅H₁₅NO
• Molecular Weight: 225.2857
• Mol File: 16285-78-2.mol

Chemical Properties

• Boiling Point: 374.6°C at 760 mmHg
• Flash Point: 110.4°C
• Density: 1.131g/cm³
• Vapor Pressure: 8.27E-06mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: 2,3-diphenyl-1,3-oxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-diphenyl-1,3-oxazolidine(16285-78-2)
• EPA Substance Registry System: 2,3-diphenyl-1,3-oxazolidine(16285-78-2)

Safety Data

• Hazardous Substances Data: 16285-78-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
2,3-diphenyl-1,3-oxazolidine is used as a pharmaceutical compound for its potential therapeutic properties. It is being studied for its possible use in the development of new drugs, particularly in the context of its antimicrobial activity, which could lead to the creation of novel antibiotics or antifungal agents.
Used in Asymmetric Synthesis:
In the field of organic chemistry, 2,3-diphenyl-1,3-oxazolidine is used as a chiral auxiliary. This application is crucial for the synthesis of enantiomerically pure compounds, which are essential in many pharmaceutical and agrochemical products, as the different enantiomers of a molecule can have vastly different biological activities.
Used in Antimicrobial Applications:
2,3-diphenyl-1,3-oxazolidine is used as an antimicrobial agent due to its ability to inhibit the growth of various microorganisms. This property makes it a candidate for the development of new antimicrobial drugs, which could be particularly important in the face of increasing antibiotic resistance.
Used in Catalytic Asymmetric Reactions:
In the chemical industry, 2,3-diphenyl-1,3-oxazolidine is used as a chiral ligand in catalytic asymmetric reactions. This role is vital for the production of optically active compounds, which are often required in the synthesis of complex molecules, such as pharmaceuticals and natural products. The use of chiral ligands can improve the selectivity and efficiency of these reactions, leading to more sustainable and cost-effective processes.

Upstream product

• 100-52-7 benzaldehyde 
• 122-98-5 2-Anilinoethanol 
• 591-50-4 iodobenzene 

Downstream Products

• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 20503-92-8 3-phenyl-oxazolidine 
• 20503-91-7 3,3'-(4,4'-methanediyl-diphenyl)-bis-oxazolidine 

Relevant articles and documents

Rediscovering aminal chemistry: Copper(ii) catalysed formation under mild conditions

Aminals, the N,N analogues of acetals, have been thoroughly explored in organic chemistry, with a particular focus on heteroaromatic aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible potential applications. By studying the stability of various aminals, we were able to develop a simple aldehyde protecting group based on a commercial diamine which is deprotected under mind conditions. We developed a protocol for the scavenging of genotoxic aldehydes by taking advantage of our methodology and a diamine resin, as well as early studies on the development of a stimuli-responsive release system using a salycil aldehyde derived aminal. This journal is

The synthesis of new 1,3-oxazolidines and 1,3-oxazinanes containing (η6-arene)tricarbonylchromium group based on condensation between aldehydes and amino alcohols

The condensation reactions of β- and γ-amino alcohols containing phenyl or (η6-arene) tricarbonylchromium substituent with formaldehyde, acetaldehyde, benzaldehyde, and (η6-benzaldehyde)tricarbonylchromium were studied. The resulting 1,3-oxazolidine and 1,3-oxazinane products were isolated in a pure form and identified by different physicochemical methods. The effect of (η6-arene)tricarbonylchromium moiety on the reaction process was demonstrated.

Synthesis of N-(dialkylaminoalkyl)alcohols by homogeneously catalyzed hydrogenolysis of cyclic N,O-acetals

The homogeneously catalyzed hydrogenation of 1,3-oxazolidines affording unsymmetrically substituted 2-N-(dialkylamino)ethanols is reported showing for the first time that Rh(I) catalysts based on chelating diphosphines can be advantageous for this reaction.

One-Pot Synthesis of Ethyl 3-(2-Hydroxyalkyl)aminoalkanoates by Ring Opening of 1,3-Oxazolidines Using Reformatsky Reagent

Oxazolidines, obtained by the condensation of aldehydes with 2-anilino-1-alkanols, react with the Refortmatsky reagent derived from ethyl bromoacetate under mild reaction conditions to afford ethyl 3-(2-hydroxyalkyl)aminoalkanoates.