tert-Butyl (2-bromothiophen-3-yl)carbamate

Name: tert-Butyl (2-bromothiophen-3-yl)carbamate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 21483-64-7
Cat. No. CS-0154424
Purity≥98%
MDL No.MFCD01927222

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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tert-Butyl (2-bromothiophen-3-yl)carbamate|CS-0154424

Structure of 21483-64-7

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General Information

CAS No. 21483-64-7
Cat. No. CS-0154424
Purity ≥98%
MDL No. MFCD01927222
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₂BrNO₂S
Molecular Weight 278.17
Synonym(s) N-Boc-3-amino-2-bromothiophene
SMILES CC(C)(OC(NC1=C(SC=C1)Br)=O)C

Description

tert-Butyl (2-bromothiophen-3-yl)carbamate is a bench-stable, moisture-tolerant building block featuring a brominated thiophene core and a protected amine. This carbamate moiety enables direct incorporation into Suzuki-Miyaura coupling reactions, while the para-bromine facilitates palladium-catalyzed cross-coupling transformations. The structure supports efficient access to functionalized heteroaryl scaffolds in medicinal chemistry and materials science applications.

Application

tert-Butyl (2-bromothiophen-3-yl)carbamate serves as a stable, bench-friendly building block for the synthesis of brominated thiophene derivatives. Its carbamate group enables orthogonal protection during synthetic sequences, while the bromine substituent facilitates palladium-catalyzed cross-coupling reactions such as Suzuki and Stille couplings. The compound exhibits excellent functional group tolerance and is readily purified by flash chromatography, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  19228-91-2
- ~93%
- In-stock
  
  21483-64-7
References
- Wyeth Patent: US2006/154875 A1, 2006 ; Location in patent: Page/Page column 7; 12 ;
Route2
- In-stock
  
  24287-95-4
- 75-65-0
- ~67%
- In-stock
  
  21483-64-7
References
- ABBOTT LABORATORIES Patent: US2011/152243 A1, 2011 ; Location in patent: Page/Page column 45 ;

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

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 (2-bromothiophen-3-yl)carbamate

CAS No. 21483-64-7

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