tert-Butyl oxirane-2-carboxylate

Name: tert-Butyl oxirane-2-carboxylate
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CAS No. 92223-80-8
Cat. No. CS-0037958
Purity≥98%
MDL No.MFCD24501779

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tert-Butyl oxirane-2-carboxylate|CS-0037958

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General Information

CAS No. 92223-80-8
Cat. No. CS-0037958
Purity ≥98%
MDL No. MFCD24501779
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₁₂O₃
Molecular Weight 144.17
Synonym(s) None
SMILES O=C(C1OC1)OC(C)(C)C

Description

tert-Butyl oxirane-2-carboxylate features a strained epoxide ring fused to a tert-butyl ester, enabling selective ring-opening reactions under mild conditions. This bench-stable, moisture-tolerant reagent integrates readily into synthetic sequences requiring stereocontrolled functionalization, particularly in the construction of chiral building blocks for medicinal chemistry and natural product synthesis.

Application

tert-Butyl oxirane-2-carboxylate serves as a stable, bench-ready building block for the synthesis of chiral epoxides and β-hydroxy carboxylic acid derivatives. Its oxirane ring undergoes regioselective ring-opening with nucleophiles under mild conditions, enabling efficient access to functionalized intermediates. The tert-butyl ester group provides excellent stability and facilitates straightforward purification via standard chromatography or crystallization. This compound functions as a versatile precursor in asymmetric synthesis and the construction of bioactive heterocyclic scaffolds.

Safety Information

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Computational Chemistry Data

TPSA 38.83
LogP 0.7269
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Oxane compounds

Key Words

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tert-Butyl oxirane-2-carboxylate

CAS No. 92223-80-8

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