tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate

Name: tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate
Brand: ChemScene
Availability: InStock
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CAS No. 1227958-32-8
Cat. No. CS-W006785
Purity≥97%
MDL No.MFCD20039978

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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+
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tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate|CS-W006785

Structure of 1227958-32-8

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General Information

CAS No. 1227958-32-8
Cat. No. CS-W006785
Purity ≥97%
MDL No. MFCD20039978
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₂BrClN₂O₂
Molecular Weight 307.57
Synonym(s) Tert-butyl N-(2-bromo-6-chloropyridin-3-yl)carbamate
SMILES O=C(NC1=CC=C(N=C1Br)Cl)OC(C)(C)C

Description

tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate features a pyridine core bearing bromo and chloro substituents at the 2- and 6-positions, respectively, with a bench-stable tert-butyl carbamate group at the 3-position. This protected amine serves as a key building block in medicinal chemistry, enabling efficient coupling reactions under mild conditions. The electron-deficient pyridine ring enhances reactivity in cross-coupling processes, while the orthogonal protecting group allows selective deprotection.

Application

tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the 2-position of the pyridine ring via palladium-catalyzed cross-coupling. The bromo group facilitates Suzuki, Stille, and Negishi reactions, while the chloro substituent offers orthogonal reactivity for sequential transformations. The carbamate protection ensures stability during synthesis and can be readily removed under mild acidic conditions. This compound is bench-stable, easily purified by flash chromatography, and compatible with diverse reaction conditions typical of API development workflows.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  1050501-88-6
- ~83%
- In-stock
  
  1227958-32-8
References
- Grongsaard, Pintipa; Bulger, Paul G.; Wallace, Debra J.; Tan, Lushi; Chen, Qinghao; Dolman, Sarah J.; Nyrop, Jason; Hoerrner, R. Scott; Weisel, Mark; Arredondo, Juan; Itoh, Takahiro; Xie, Chengfu; Wen, Xianghui; Zhao, Dalian; Muzzio, Daniel J.; Bassan, Ephraim M.; Shultz, C. Scott Organic Process Research and Development, 2012 , vol. 16, # 5 p. 1069 - 1081
Route2
- In-stock
  
  5350-93-6
- ~%
- In-stock
  
  1227958-32-8
References
- Organic Process Research and Development, , vol. 16, # 5 p. 1069 - 1081

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 3.8445
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Chloride

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl (2-bromo-6-chloropyridin-3-yl)carbamate

CAS No. 1227958-32-8

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