Rivaroxaban impurity 43

CAS No. 181140-34-1
Cat. No. CS-M0558
Molecule weight203.20
Purity≥98%
MDL No.MFCD04973349

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Structure of 181140-34-1

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General Information

CAS No. 181140-34-1
Cat. No. CS-M0558
Purity ≥98%
MDL No. MFCD04973349
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₉NO₃
Molecular Weight 203.20
Synonym(s) None
SMILES O=C1C=2C(C(=O)N1C[C@@H]3CO3)=CC=CC2

Description

This chiral epoxide integrates seamlessly into asymmetric synthesis, where the oxiran-2-ylmethyl moiety enables stereoselective ring-opening reactions. The isoindoline-1,3-dione core provides a rigid, electron-deficient scaffold ideal for conjugate additions and transition-metal-catalyzed transformations under standard conditions.

Application

(R)-2-(oxiran-2-ylmethyl)isoindoline-1,3-dione serves as a versatile chiral building block for the synthesis of complex heterocycles and bioactive molecules. The epoxide moiety enables stereoselective ring-opening reactions with nucleophiles, while the isoindoline-1,3-dione scaffold provides excellent functional group tolerance and stability under standard reaction conditions. Its well-defined stereochemistry facilitates the construction of enantioselective scaffolds relevant to medicinal chemistry and natural product synthesis.

Synthesis

Route1
- 136918-14-4
- 57044-25-4
- ~84%
- In-stock
  
  181140-34-1
References
- Gutcait, Alexander; Wang, Kuang-Chao; Liu, Hsiu-Wen; Chern, Ji-Wang Tetrahedron Asymmetry, 1996 , vol. 7, # 6 p. 1641 - 1648
Route2
- In-stock
  
  19667-37-9
- ~72%
- In-stock
  
  181140-34-1
References
- DAISO CO., LTD. Patent: EP1403267 A1, 2004 ; Location in patent: Page 6 ;
Route3
- 136918-14-4
- 51594-55-9
- ~90%
- In-stock
  
  181140-34-1
References
- Miki, Yasushi; Mikami, Masafumi Patent: US2006/19993 A1, 2006 ; Location in patent: Page/Page column 5 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05
Signal Word : Danger	UN#: 3261
Class : 8	Packing Group : Ⅲ
Hazard Statements : H318
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

TPSA 49.91
LogP 0.6814
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Oxane compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

General Reagents Organic General Reagents

Key Words

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Rivaroxaban impurity 43

CAS No. 181140-34-1

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