tert-Butyl N-(5-bromothiophen-2-yl)carbamate

Name: tert-Butyl N-(5-bromothiophen-2-yl)carbamate
Brand: ChemScene
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CAS No. 943321-89-9
Cat. No. CS-0048061
Purity≥95%
MDL No.None

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tert-Butyl N-(5-bromothiophen-2-yl)carbamate|CS-0048061

Structure of 943321-89-9

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General Information

CAS No. 943321-89-9
Cat. No. CS-0048061
Purity ≥95%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₂BrNO₂S
Molecular Weight 278.17
Synonym(s) tert-Butyl (5-bromothiophen-2-yl)carbamate
SMILES CC(C)(C)OC(=O)NC1=CC=C(Br)S1

Description

tert-Butyl N-(5-bromothiophen-2-yl)carbamate features a brominated thiophene scaffold with a bench-stable tert-butyl carbamate protecting group, enabling direct incorporation into cross-coupling and cyclization sequences. The para-bromo functionality facilitates palladium-catalyzed transformations, while the carbamate moiety offers orthogonal protection for amine-directed synthesis in medicinal chemistry and materials development.

Application

tert-Butyl N-(5-bromothiophen-2-yl)carbamate serves as a stable, bench-friendly building block for the synthesis of brominated thiophene-containing scaffolds. The tert-butyl carbamate group provides excellent stability and orthogonal deprotection under mild acidic conditions, enabling sequential functionalization. It readily participates in palladium-catalyzed cross-coupling reactions, facilitating efficient access to biologically relevant heterocyclic architectures and complex molecular frameworks in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  7311-63-9
- 75-65-0
- ~60%
- In-stock
  
  943321-89-9
References
- Seefeld, Mark A.; Rouse, Meagan B.; McNulty, Kenneth C.; Sun, Lihui; Wang, Jizhou; Yamashita, Dennis S.; Luengo, Juan I.; Zhang, ShuYun; Minthorn, Elisabeth A.; Concha, Nestor O.; Heerding, Dirk A. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 8 p. 2244 - 2248

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-H413
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 3.8576
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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tert-Butyl N-(5-bromothiophen-2-yl)carbamate

CAS No. 943321-89-9

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