Benzyl 4-oxoazetidine-2-carboxylate

Name: Benzyl 4-oxoazetidine-2-carboxylate
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CAS No. 87791-58-0
Cat. No. CS-0149861
Purity≥96%
MDL No.MFCD00661973

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FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Benzyl 4-oxoazetidine-2-carboxylate|CS-0149861

Structure of 87791-58-0

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General Information

CAS No. 87791-58-0
Cat. No. CS-0149861
Purity ≥96%
MDL No. MFCD00661973
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₁NO₃
Molecular Weight 205.21
Synonym(s) 4-(Benzyloxycarbonyl)-2-azetidinone
SMILES O=C(C1CC(N1)=O)OCC2=CC=CC=C2

Description

Benzyl 4-oxoazetidine-2-carboxylate features a strained azetidine ring with a carbonyl at the 4-position and a benzyl ester at C2, offering a reactive handle for synthetic transformations. This electron-deficient heterocycle integrates readily into peptide mimetics and bioactive scaffolds, enabling efficient access to constrained analogs under standard conditions.

Application

Benzyl 4-oxoazetidine-2-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to strained azetidine scaffolds. Its ketone functionality facilitates nucleophilic addition and reductive amination, while the benzyl ester allows for straightforward deprotection under mild conditions. The compound exhibits good bench stability and functional group tolerance, making it well-suited for use in medicinal chemistry campaigns involving heterocyclic core construction and late-stage derivatization.

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

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Computational Chemistry Data

TPSA 55.4
LogP 0.6183
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Azetidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl 4-oxoazetidine-2-carboxylate

CAS No. 87791-58-0

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