Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate

Name: Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate
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CAS No. 149587-72-4
Cat. No. CS-0037157
Purity≥98%
MDL No.MFCD01763684

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Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate|CS-0037157

Structure of 149587-72-4

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General Information

CAS No. 149587-72-4
Cat. No. CS-0037157
Purity ≥98%
MDL No. MFCD01763684
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅NO₄S
Molecular Weight 257.31
Synonym(s) methyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]thiophene-2-carboxylate
SMILES CC(C)(C)OC(=NC1=C(C(=O)OC)SC=C1)O

Description

Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate features a thiophene core functionalized with a boronate ester and a protected amine, enabling direct coupling in Suzuki-Miyaura reactions. The tert-butyl carbamate group ensures stability during handling and facilitates selective deprotection. This bench-stable intermediate integrates efficiently into complex heterocyclic scaffolds for medicinal chemistry applications.

Application

Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate serves as a versatile building block for thiophene-based heterocycles, enabling straightforward access to bioactive scaffolds via standard deprotection and coupling reactions. The Boc-protected amine offers excellent bench stability and compatibility with diverse functional groups, while the ester moiety facilitates selective transformations. This compound functions reliably in peptide-like coupling protocols and serves as a key intermediate in the synthesis of medicinally relevant thiophene derivatives.

Synthesis

Route1
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References
- BAYER PHARMACEUTICALS CORPORATION Patent: WO2006/23707 A2, 2006 ; Location in patent: Page/Page column 34 ; WO 2006/023707 A2

Safety Information

Download SDS

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 68.12
LogP 2.8953
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate

CAS No. 149587-72-4

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