5-AMINO-3-BROMO (1H)INDAZOLE

Base Information

• Chemical Name: 5-AMINO-3-BROMO (1H)INDAZOLE
• CAS No.: 478837-59-1
• Molecular Formula: C7H6BrN3
• Molecular Weight: 212.049
• Hs Code.: 2933990090
• Mol file: 478837-59-1.mol

Synonyms:3-Bromo-1H-indazol-5-amine;5-Amino-3-bromoindazole;

Chemical Property of 5-AMINO-3-BROMO (1H)INDAZOLE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.8
• Boiling Point: 431.342 °C at 760 mmHg
• PKA: 12.34±0.40(Predicted)
• Flash Point: 214.668 °C
• PSA: 54.70000
• Density: 1.867 g/cm³
• LogP: 2.48880
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-1H-indazol-5-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Bromo-1H-indazol-5-amine acts as a reagent for the preparation of Polycyclic indazole derivatives that are ERK inhibitors and their use in the treatment and prevention of cancer, anilino quinazolines as antitumor agents.

Technology Process of 5-AMINO-3-BROMO (1H)INDAZOLE

There total 2 articles about 5-AMINO-3-BROMO (1H)INDAZOLE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

3-bromo-5-nitro-1H-indazole (67400-25-3) → 3-bromo-1H-indazol-5-amine (478837-59-1)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; at 80 ℃; for 1h;

Reference yield:

5-nitroindazole (5401-94-5) → 3-bromo-1H-indazol-5-amine (478837-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; bromine / 1,4-dioxane; water / 4 h / 0 - 20 °C

2: tin(ll) chloride / DMF (N,N-dimethyl-formamide) / 1.5 h / 70 °C

With sodium hydroxide; bromine; tin(ll) chloride; In 1,4-dioxane; DMF (N,N-dimethyl-formamide); water;

Reference yield: 98.0%

3-bromo-1H-indazol-5-amine (478837-59-1) + m-tolylboronic acid (17933-03-8) → C14H13N3 (1175793-77-7)

Guidance literature:

With potassium phosphate; palladium diacetate; ruphos; In 1,4-dioxane; water; at 140 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.tetlet.2015.04.024

upstream raw materials:

3-bromo-5-nitro-1H-indazole

5-nitroindazole

Downstream raw materials:

1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid (3-bromo-1H-indazol-5-yl)-amide

N-(3-bromo-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide

3-phenyl-1H-indazol-5-amine

C₁₄H₁₃N₃O

Refernces

Efficient synthesis of 3-aryl-1H-indazol-5-amine by Pd-catalyzed Suzuki-Miyaura cross-coupling reaction under microwave-assisted conditions

10.1016/j.tetlet.2015.04.024

The research presents an efficient method for synthesizing various 3-aryl-1H-indazol-5-amine derivatives using a Pd-catalyzed Suzuki–Miyaura cross-coupling reaction under microwave-assisted conditions. The study focuses on optimizing the reaction conditions to achieve high yields and efficiency. The key chemicals involved in this research include 3-bromo-indazol-5-amine as the starting material, arylboronic acids as coupling partners, Pd(OAc)2 as the palladium catalyst, RuPhos as the ligand, and K3PO4 as the base. The reaction is carried out in a dioxane/H2O solvent system at 140°C for 30 minutes under microwave irradiation. The optimized conditions enable the synthesis of a wide range of 3-aryl-1H-indazol-5-amine derivatives with various functional groups, demonstrating the versatility and applicability of this method for library biological active screening.