5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine 2629245-96-9 Purity 98% Pharmaceutical Intermediate

1. Product Overview

5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine (CAS: 2629245-96-9) is a brominated fused azole heterocycle that combines a [1,2,4]triazolo[1,5-a]pyridine core with a reactive 2‑amino group and a 5‑bromo substituent. With the molecular formula C₆H₅BrN₄ and a molecular weight of 213.04 g/mol, this compound is a high‑utility building block in medicinal chemistry. The triazolopyridine scaffold is a well‑established bioisostere of purines and imidazopyridines, frequently employed to enhance metabolic stability and modulate solubility in drug candidates. The orthogonal reactivity—nucleophilic amine at C2 and electrophilic bromine at C5—enables sequential, metal‑catalyzed cross‑coupling followed by amide/urea formation or nucleophilic aromatic substitution.

2. Key Features & Advantages

• Orthogonal Functional Handles: C5‑Br is highly active in Suzuki, Sonogashira, and Stille couplings; the C2‑NH₂ allows acylation, sulfonylation, condensation, or diazotization without protecting the bromine in many protocols.

• Bioisosteric Scaffold: The [1,2,4]triazolo[1,5-a]pyridine core mimics adenine/imidazo[1,2-a]pyridine, making it valuable for kinase hinge‑binding motifs and CNS‑penetrant agents.

• Crystalline & Stable: Isolates as a well‑defined off‑white to pale yellow crystalline solid, facilitating purification and ensuring batch‑to‑batch reproducibility at ≥98% HPLC purity.

• Broad Reaction Compatibility: Stable to common organic bases (K₂CO₃, Et₃N, DIPEA) and mild acids; compatible with Pd‑catalyzed conditions and microwave‑assisted synthesis.

• Full Analytical Package: Supplied with ¹H/¹³C NMR, HPLC, LC‑MS/HRMS, and melting point data to support pharma‑grade custom synthesis and regulatory documentation.

3. Main Applications

• Pharmaceutical Intermediate: Core unit in kinase inhibitor programs (e.g., BTK, JAK, CDK scaffolds), where the triazolopyridine acts as a purine bioisostere in ATP‑site binders.

• Medicinal Chemistry Libraries: Used in diversity‑oriented synthesis—(1) Pd‑couple Br → biaryl/styryl triazolopyridines; (2) acylate/sulfonylate 2‑NH₂ → amides/sulfonamides/ureas; (3) condense NH₂ with aldehydes → imines for further cyclization.

• Antiviral & CNS Research: Triazolopyridine derivatives are explored as antiviral agents (including SARS‑CoV‑2 Mpro modulators) and CNS drugs due to favorable logP and hydrogen‑bonding.

• PROTAC & Chemical Probe Design: The bromine provides a handle to install linkers via cross‑coupling, while the amine can anchor warheads or E3‑ligase recruiting groups.

• Agrochemical Leads: Azole‑fused pyridines are common in modern fungicide/insecticide scaffolds; this intermediate supports crop‑protection R&D.

4. Technical Specifications

5. Storage & Handling

• Storage Conditions: Store in a cool, dry place at 2–8 °C in a tightly sealed amber glass vial, preferably under an inert atmosphere (N₂ or Ar) for long‑term storage (>12 months). Protect from light and moisture. For routine R&D, keep desiccated at 2–8 °C.

• Handling: Weigh in a fume hood to avoid dust inhalation. The amine group may darken on air exposure—minimize open‑vial time. Use anhydrous solvents if performing Pd‑couplings or amine acylations. Standard PPE: nitrile gloves, safety goggles, lab coat.

• Packaging: Supplied in septum‑capped amber vials (0.1 g, 1 g, 5 g, 25 g) with desiccant; bulk in double‑poly‑lined foil bags (100 g–1 kg) under argon.

• Shelf Life: 24 months from manufacture when stored as recommended; retest if color deepens to orange/yellow.

6. Safety Overview

Intended strictly for laboratory research, custom synthesis, and industrial intermediate use—not for human or veterinary therapeutic use, food, or cosmetics.

• Hazard Profile (GHS‑typical for bromo‑azaheterocyclic amine):

• H302: Harmful if swallowed.

• H315: Causes skin irritation.

• H319: Causes serious eye irritation.

• H335: May cause respiratory irritation (dust).

• H412: Harmful to aquatic life with long‑lasting effects (brominated heterocycle precaution).

• Precautionary Statements:

• P261: Avoid breathing dust/fume/gas/mist/vapors/spray.

• P264: Wash hands thoroughly after handling.

• P271: Use only outdoors or in a well‑ventilated area (fume hood).

• P280: Wear protective gloves, eye/face protection, and lab coat.

• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present; continue rinsing.

• P391: Collect spillage.

• P501: Dispose of contents/container in accordance with local regulations for halogenated organic waste.

• First Aid:

• Skin: Remove contaminated clothing. Wash with plenty of soap and water. If irritation develops, seek medical advice.

• Eyes: Irrigate immediately with flowing water for at least 15 minutes, holding eyelids open. Get medical attention.

• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water if conscious. Seek medical help.

• Inhalation: Move to fresh air. If breathing difficult, administer oxygen and consult physician.

A full GHS‑compliant Safety Data Sheet (SDS) is available upon request for ECHEMI listing and customer distribution.