(S)-4-(Hydroxymethyl)oxazolidin-2-one

Name: (S)-4-(Hydroxymethyl)oxazolidin-2-one
Brand: ChemScene
Availability: InStock
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CAS No. 144542-44-9
Cat. No. CS-0067476
Purity≥97%
MDL No.MFCD11847630

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(S)-4-(Hydroxymethyl)oxazolidin-2-one|CS-0067476

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General Information

CAS No. 144542-44-9
Cat. No. CS-0067476
Purity ≥97%
MDL No. MFCD11847630
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₇NO₃
Molecular Weight 117.10
Synonym(s) (4S)-4-(Hydroxymethyl)-1,3-oxazolidin-2-one
SMILES O=C1OC[C@H](CO)N1

Description

(S)-4-(Hydroxymethyl)oxazolidin-2-one is a chiral synthon featuring a stereodefined oxazolidinone core and a pendant hydroxymethyl group. This configurationally stable scaffold enables direct incorporation into complex molecular architectures, particularly in asymmetric synthesis and peptide backbone modification. The hydroxymethyl moiety provides a versatile handle for further functionalization, enhancing its utility in medicinal chemistry and catalyst design.

Application

(S)-4-(Hydroxymethyl)oxazolidin-2-one serves as a versatile chiral building block in synthetic organic chemistry, enabling stereoselective transformations through its pendant hydroxyl and carbonyl functionalities. Its oxazolidinone core provides excellent stability and facilitates efficient derivatization, including nucleophilic substitution and reductive amination reactions. The molecule functions as a key intermediate in the synthesis of bioactive heterocycles and peptide mimetics, offering predictable stereocontrol and compatibility with standard purification techniques.

Synthesis

Route1
- In-stock
  
  96751-61-0
- ~%
- In-stock
  
  144542-44-9
References
- Vertex Pharmaceuticals, Incorporated Patent: US6372778 B1, 2002 ; Location in patent: Example 109 ;US 6372778 B1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P210-P243-P273-P403

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Computational Chemistry Data

TPSA 58.56
LogP -0.9129
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Key Words

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(S)-4-(Hydroxymethyl)oxazolidin-2-one

CAS No. 144542-44-9

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