(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

Name: (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one
Brand: ChemScene
Availability: InStock
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CAS No. 184346-45-0
Cat. No. CS-W010043
Molecule weight281.35
Purity≥97%
MDL No.MFCD03093556

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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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(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one|CS-W010043

Structure of 184346-45-0

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General Information

CAS No. 184346-45-0
Cat. No. CS-W010043
Purity ≥97%
MDL No. MFCD03093556
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₉NO₂
Molecular Weight 281.35
Synonym(s) (4S)-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
SMILES O=C1OC(C2=CC=CC=C2)([C@H](C(C)C)N1)C3=CC=CC=C3

Description

(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one is a chiral oxazolidinone scaffold featuring a sterically encumbered diphenyl-substituted ring and an isopropyl group at the 4-position. This configuration imparts high enantioselectivity in asymmetric synthesis, particularly in nucleophilic additions and catalytic transformations. The bench-stable, moisture-tolerant structure facilitates handling under standard conditions.

Application

(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one serves as a robust chiral auxiliary in asymmetric synthesis, enabling high diastereoselective transformations through well-established enolate chemistry. Its bench-stable oxazolidinone core offers excellent functional group tolerance and facilitates stereoselective C–C bond formation, particularly in aldol and alkylation reactions. The diphenyl substitution enhances rigidity and stereocontrol, while the isopropyl group improves solubility and purification efficiency. Widely employed in medicinal chemistry workflows, it functions as a reliable scaffold for constructing complex chiral intermediates with predictable stereochemical outcomes.

Synthesis

Route1
- 67-56-1
- 916830-67-6
- 124-41-4
- ~98%
- 1032199-09-9
- In-stock
  
  184346-45-0
References
- EP2103603 A1, ; Page/Page column 97 ; EP 2103603 A1
Route2
- 32315-10-9
- In-stock
  
  78603-95-9
- ~73%
- In-stock
  
  184346-45-0
References
- Alexander; Cook; Gibson; Kennedy Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 13 p. 1538 - 1549
Route3
- 213887-92-4
- ~78%
- 14367-67-0
- In-stock
  
  184346-45-0
References
- Helvetica Chimica Acta, , vol. 81, # 11 p. 2093 - 2126

Safety Information

Download SDS

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

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 3.6946
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Chiral compounds Chiral Auxiliaries

Catalysis Asymmetric Synthesis Chiral Auxiliaries

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(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

CAS No. 184346-45-0

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