tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate

Name: tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate
Brand: ChemScene
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CAS No. 1188477-11-3
Cat. No. CS-W005657
Purity≥95%
MDL No.MFCD11520868

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate|CS-W005657

Structure of 1188477-11-3

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General Information

CAS No. 1188477-11-3
Cat. No. CS-W005657
Purity ≥95%
MDL No. MFCD11520868
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅BrN₂O₂
Molecular Weight 287.15
Synonym(s) tert-butyl N-[(5-bromopyridin-2-yl)methyl]carbamate
SMILES O=C(NCC1=NC=C(C=C1)Br)OC(C)(C)C

Description

tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate delivers a brominated pyridyl methyl scaffold with orthogonal protection, enabling direct functionalization at the 5-position. This bench-stable reagent integrates readily into cross-coupling workflows, where the carbamate group facilitates purification and selective deprotection.

Application

tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate serves as a versatile building block in medicinal chemistry, enabling the efficient introduction of a brominated pyridine moiety via orthogonal N-Boc deprotection. Its stability under standard reaction conditions and compatibility with palladium-catalyzed cross-coupling reactions facilitate rapid access to functionalized heterocycles. The Boc-protected amine allows for selective transformations, while the pendant bromide supports diverse late-stage modifications, making it ideal for scaffold diversification in API development.

Synthesis

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References
- Curtis, Michael; Duclos, Brian A.; Ewin, Richard A.; Johnson, Paul D.; Johnson, Timothy Allen; Vairagoundar, Rajendran; Billen, Denis; Goodwin, Richard M.; Haber-Stuk, Andrea K.; Kyne, Graham M.; Sheehan, Susan M. K. Patent: US2013/237502 A1, 2013 ; Location in patent: Paragraph 0367 ;

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 51.22
LogP 2.8688
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate

CAS No. 1188477-11-3

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