(R)-4-Methyloxazolidin-2-one

Name: (R)-4-Methyloxazolidin-2-one
Brand: ChemScene
Availability: InStock
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CAS No. 4042-43-7
Cat. No. CS-0158229
Purity≥98%
MDL No.MFCD06656588

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 4042-43-7

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General Information

CAS No. 4042-43-7
Cat. No. CS-0158229
Purity ≥98%
MDL No. MFCD06656588
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₇NO₂
Molecular Weight 101.10
Synonym(s) (4R)-4-Methyl-2-oxazolidinone
SMILES C[C@@H]1COC(N1)=O

Description

(R)-4-Methyloxazolidin-2-one is a chiral synthon featuring a rigid oxazolidinone ring with defined stereochemistry at the 4-position. This bench-stable heterocycle integrates seamlessly into asymmetric synthesis, serving as a stereoselective auxiliary in enantiocontrolled transformations. Its electron-deficient carbonyl and adjacent nitrogen enable precise nucleophilic attack pathways, facilitating efficient coupling reactions under mild conditions.

Application

(R)-4-Methyloxazolidin-2-one serves as a chiral synthon in asymmetric synthesis, enabling stereoselective C–C and C–heteroatom bond formation. Its stable oxazolidinone core exhibits excellent functional group tolerance and facilitates enantioselective transformations via well-established routes. The compound functions as a versatile building block for medicinal chemistry applications, particularly in the construction of β-amino acid derivatives and peptidomimetics. Bench-stable and readily purified by standard chromatography, it supports scalable synthesis workflows.

Synthesis

Route1
- In-stock
  
  35320-23-1
- 105-58-8
- ~58%
- In-stock
  
  4042-43-7
References
- Adam, Waldemar; Bosio, Sara G.; Turro, Nicholas J. Journal of the American Chemical Society, 2002 , vol. 124, # 30 p. 8814 - 8815
Route2
- In-stock
  
  28875-17-4
- ~%
- In-stock
  
  4042-35-7
- In-stock
  
  4042-43-7
References
- Kuriyama, Wataru; Ino, Yasunori; Ogata, Osamu; Sayo, Noboru; Saito, Takao Advanced Synthesis and Catalysis, 2010 , vol. 352, # 1 p. 92 - 96
Route3
- In-stock
  
  35320-23-1
- 32315-10-9
- ~%
- In-stock
  
  4042-43-7
References
- Chouhan, Gagan; Alper, Howard Journal of Organic Chemistry, 2009 , vol. 74, # 16 p. 6181 - 6189

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 0.1147
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Key Words

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(R)-4-Methyloxazolidin-2-one

CAS No. 4042-43-7

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