tert-Butyl 2-(prop-2-yn-1-yloxy)acetate

Name: tert-Butyl 2-(prop-2-yn-1-yloxy)acetate
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CAS No. 339531-55-4
Cat. No. CS-0612222
Purity≥97%
MDL No.MFCD29087247

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tert-Butyl 2-(prop-2-yn-1-yloxy)acetate|CS-0612222

Structure of 339531-55-4

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General Information

CAS No. 339531-55-4
Cat. No. CS-0612222
Purity ≥97%
MDL No. MFCD29087247
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₄O₃
Molecular Weight 170.21
Synonym(s) None
SMILES O=C(OC(C)(C)C)COCC#C

Description

tert-Butyl 2-(prop-2-yn-1-yloxy)acetate is a bench-stable, moisture-tolerant building block featuring a propargylic ether linkage and a tert-butyl ester group. This combination enables direct incorporation into Sonogashira coupling reactions and facilitates selective deprotection under mild acidic conditions. The alkyne moiety supports downstream functionalization via click chemistry, while the ester serves as a protected carboxylic acid handle for peptide and macrocycle synthesis.

Application

tert-Butyl 2-(prop-2-yn-1-yloxy)acetate serves as a versatile building block in synthetic organic chemistry, enabling efficient introduction of both propargylic ether and ester functionalities. The molecule exhibits excellent bench stability and facilitates orthogonal protection strategies, particularly in multi-step syntheses involving alkyne-based coupling reactions or selective deprotection sequences. Its compatibility with palladium-catalyzed transformations and tolerance to common reaction conditions make it well-suited for the construction of complex scaffolds in medicinal chemistry and process development workflows.

Safety Information

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Computational Chemistry Data

TPSA 35.53
LogP 0.9779
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Fatty chain compounds

Building Blocks Functional Group Boc

Building Blocks Functional Group Ether

Building Blocks Functional Group Alkyne

Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Terminal Alkynes

Chemical Biology Conjugation Chemistry/Click Chemistry Terminal Alkynes

Key Words

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tert-Butyl 2-(prop-2-yn-1-yloxy)acetate

CAS No. 339531-55-4

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