2-(Boc-amino)-5-bromopyridine
[CAS# 159451-66-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Bromopyridine
• Name: 2-(Boc-amino)-5-bromopyridine
• Molecular Formula: C₁₀H₁₃BrN₂O₂
• Molecular Weight: 273.13
• CAS Registry Number: 159451-66-8
• EC Number: 629-082-1
• SMILES: CC(C)(C)OC(=O)NC1=NC=C(C=C1)Br

Properties

• Melting point: 167-171 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H317-H319
• Precautionary Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

2-(Boc-amino)-5-bromopyridine is a widely used compound with applications in pharmaceutical and chemical research. It features a pyridine ring substituted with a bromine atom at the 5-position and a tert-butyloxycarbonyl (Boc) protected amino group at the 2-position. The development of 2-(Boc-amino)-5-bromopyridine stems from the need for functionalized pyridines in organic synthesis and medicinal chemistry. Pyridine derivatives play a vital role in drug discovery and development, being able to mimic natural compounds and effectively bind to biological targets.

The compound consists of a pyridine ring with a bromine atom at the 5-position and a Boc protected amino group at the 2-position. The Boc group provides protection to the amino group, making the molecule more stable and easier to handle in various reactions. It is a white to off-white crystalline powder that is soluble in organic solvents such as methanol, dichloromethane, and dimethyl sulfoxide (DMSO), but slightly soluble in water. Its bromine atom can undergo substitution reactions, while the Boc group can be removed under acidic conditions, exposing the free amino group and facilitating further functionalization.

2-(Boc-amino)-5-bromopyridine is a key intermediate in the synthesis of various pharmaceutical compounds. Its pyridine core is common in many drugs, and the functional groups of the compound can be used to create a wide range of chemical derivatives. In drug development, it acts as a building block for the construction of more complex heterocyclic systems. These systems are essential for the development of bioactive molecules, including kinase inhibitors and enzyme modulators.

The bromine atom in 2-(Boc-amino)-5-bromopyridine is well suited for the Suzuki coupling reaction. This reaction, which couples aryl or vinyl boronic acids with halides to form biaryls or styrene derivatives, is widely used in organic synthesis to make complex molecular structures. It is also used in the Buchwald-Hartwig amination, which forms a C-N bond by coupling aryl halides with amines. The process is valuable in the synthesis of aromatic amines, which are key ingredients in pharmaceuticals and materials science.

2-(Boc-amino)-5-bromopyridine is used to design functional materials, including organic semiconductors and light-emitting compounds. Its ability to participate in a variety of coupling reactions enables the development of materials with specific electronic and optical properties. The compound is also used to introduce pyridine units into polymer chains, enhancing their thermal and chemical stability. These polymers can be used in coatings, adhesives, and electronic materials.

It is used to synthesize molecular probes for biological research. These probes help study cellular processes and detect specific biomolecules, promoting advances in diagnostic and therapeutic technologies. The Boc-protected amino groups can be deprotected to create reactive sites for bioconjugation, facilitating the attachment of biomolecules or drugs to various platforms for targeted delivery or imaging.