132682-23-6

Basic information

• Product Name: (R)-4-(Hydroxymethyl)oxazolidin-2-one
• Synonyms: (R)-4-(Hydroxymethyl)oxazolidin-2-one
• CAS NO: 132682-23-6
• Molecular Formula: C₄H₇NO₃
• Molecular Weight: 117.10328
• Mol File: 132682-23-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 95-97 °C
• Boiling Point: 430.6±14.0 °C(Predicted)
• Appearance: /
• Density: 1.288±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Sparingly, Sonicated), Water (Slightly)
• PKA: 12.11±0.40(Predicted)
• CAS DataBase Reference: (R)-4-(Hydroxymethyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(Hydroxymethyl)oxazolidin-2-one(132682-23-6)
• EPA Substance Registry System: (R)-4-(Hydroxymethyl)oxazolidin-2-one(132682-23-6)

Safety Data

• Hazardous Substances Data: 132682-23-6(Hazardous Substances Data)

Usage

Description

(R)-4-(Hydroxymethyl)oxazolidin-2-one is an organic compound that serves as a versatile building block in the field of chemical synthesis. It is characterized by its unique structure, which includes an oxazolidinone ring with a hydroxymethyl group at the 4-position and a stereocenter at the 2-position, making it a valuable component in the creation of various complex molecules.

Uses

Used in Chemical Synthesis:
(R)-4-(Hydroxymethyl)oxazolidin-2-one is used as a building block for the synthesis of various complex molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and functional groups allow for a wide range of reactions and modifications, making it a valuable starting material for the development of new compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-4-(Hydroxymethyl)oxazolidin-2-one is used as a key intermediate in the synthesis of various drugs. Its unique structure and reactivity enable the development of novel therapeutic agents with improved efficacy and selectivity, contributing to the advancement of medical treatments for a wide range of diseases and conditions.
Used in Agrochemical Industry:
(R)-4-(Hydroxymethyl)oxazolidin-2-one is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its incorporation into these products can lead to the development of more effective and environmentally friendly solutions for pest control and crop protection, ultimately benefiting agricultural productivity and sustainability.
Used in Specialty Chemicals:
In the specialty chemicals sector, (R)-4-(Hydroxymethyl)oxazolidin-2-one is employed as a building block for the development of innovative materials with unique properties. These materials can be used in various applications, such as coatings, adhesives, and polymers, where their enhanced performance characteristics can provide significant advantages over traditional materials.

Upstream product

• 96751-61-0 (S)-4-methoxycarbonyl-oxazolidin-2-one 
• 155398-62-2 (4S)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-oxazolidin-2-one 
• 15546-08-4 4-Hydroxymethyl oxazolidin-2-one 
• 264621-69-4 ethyl (S)-2-oxooxazolidinine-4-carboxylate 

Downstream Products

• 154669-49-5 [(S)-2-oxooxazolidin-4-yl]methyl-4-methylbenzenesulfonate 

Relevant articles and documents

Design and synthesis of analogues of the sphingosine-1-phosphate receptor 1 agonist IMMH001 with improved phosphorylation rate in human blood

IMMH001, which is a prodrug for sphingosine-1-phosphate receptor 1 (S1P1) agonist, is converted to the active form, its monophosphate ester (S)-IMMH001-P, by sphingosine kinase 1 (SphK1) and sphingosine kinase 2 (SphK2) in vivo. In this study, we designed head-piece-modified analogues of IMMH001 based on structural information and prepared them with an efficient modular synthetic strategy. The analogues showed higher phosphorylation rates in human blood than the parent compound. These results indicated that the pro-R hydroxymethyl in the head-piece-moiety of IMMH001 prevents the pro-S hydroxymethyl from being phosphorylated by the kinase and ATP. The analogues may have better therapeutic potential.

NOVEL BENZODIOXANE-PIPERIDINE DERIVATIVES AND THEIR THERAPEUTIC APPLICATIONS FOR TREATING NEUROPSYCHIATRIC DISORDERS

The present invention concerns benzodioxane-piperidine with general formula I: wherein notably: R1 represents one or more identical or different substituent(s) on the benzene ring, each independently representing a hydrogen or halogen atom, or a C1-4 alkyl group, or a C1-4 alkoxy group or a C1-4 hydroxyalkyl group or a C1-4 alkylcarbonyl or an alkoxycarbonyl group or an OH group or an SO2R group with R alkyl, or a CN group, or a CF3 group, or an OCF 3 group; n=1, 2 or 3;m=0 or 1, andR2 represents one or more identical or different substituent(s) on the oxazolidinone or morpholinone ring, each independently representing: a hydrogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group, or a C1-4 hydroxyalkyl group, or an alkylcarbonyl group, or an alkoxycarbonyl group, or an alkoxyphenyl group.

2,6-Disubstituted and 2,2,6-trisubstituted piperidines from serine: Asymmetric synthesis and further elaboration

(Figure presented) 4-Hydroxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl esters, which are readily prepared from serine and terminal acetylenes, undergo Claisen rearrangement to piperidine derivatives when heated with butyl vinyl ether in the presence of Hg(OAc)2 and Et3N. This route to optically pure piperidines having substituents α to nitrogen is general, and the rearrangement products are versatile intermediates for making a broad range of amines containing a substituted piperidine subunit.