3-Amino-5-bromopyridine

Base Information

• Chemical Name: 3-Amino-5-bromopyridine
• CAS No.: 13535-01-8
• Molecular Formula: C5H5BrN2
• Molecular Weight: 173.012
• Hs Code.: 29339900
• European Community (EC) Number: 629-312-0
• DSSTox Substance ID: DTXSID90355834
• Nikkaji Number: J81.639F
• Wikidata: Q72438916
• Mol file: 13535-01-8.mol

Synonyms:3-Amino-5-bromopyridine;13535-01-8;5-bromopyridin-3-amine;5-Bromo-3-pyridinamine;5-Bromo-pyridin-3-ylamine;5-bromo-3-aminopyridine;3-amino-5-bromo pyridine;3-PYRIDINAMINE, 5-BROMO-;5-bromopyridin-3-ylamine;MFCD01646060;5-amino-3-bromopyridine;3-amino-5-bromo-pyridine;3-bromo-5-amino pyridine;5-amino-3-bromo-pyridine;5-bromo-3-amino-pyridine;5-bromo-pyridine-3-amine;SCHEMBL116722;3-Amino-5-bromopyridine, 97%;DTXSID90355834;MDQXGHBCDCOOSM-UHFFFAOYSA-N;BCP22135;CS-D0805;BBL100165;STL227659;AKOS000272821;AC-9489;FS-2037;PB12251;HY-66052;SY006230;AM20050792;FT-0636912;EN300-105759;AC-907/30003012;W-205463

Chemical Property of 3-Amino-5-bromopyridine

Chemical Property:

• Appearance/Colour: Light yellow crystal
• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 65-69 ºC
• Refractive Index: 1.607
• Boiling Point: 287.6 ºC at 760mmHg
• PKA: 3.81±0.20(Predicted)
• Flash Point: 127.7 ºC
• PSA: 38.91000
• Density: 1.71 g/cm³
• LogP: 2.00750
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 171.96361
• Heavy Atom Count: 8
• Complexity: 76.8

Purity/Quality:

99% ^*data from raw suppliers

3-Amino-5-bromopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,O
• Hazard Codes: Xn,Xi,O
• Statements: 22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC=C1Br)N
• Uses: 3-Amino-5-bromopyridine is used in green preparation of tryptamine salicylic acid compounds as antitumor agent.

Technology Process of 3-Amino-5-bromopyridine

There total 10 articles about 3-Amino-5-bromopyridine 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: 96.0%

3-bromo-5-nitro-pyridine (15862-30-3) → 3-amino-5-bromopyridine (13535-01-8)

Guidance literature:

With tetrahydroxydiboron; palladium on activated charcoal; water; In acetonitrile; at 50 ℃; for 24h; Inert atmosphere;

Reference yield: 77.0%

5-Br-(3-pyridinyl)MgBr*LiCl → 3-amino-5-bromopyridine (13535-01-8)

Guidance literature:

5-Br-(3-pyridinyl)MgBr*LiCl; With copper(I) chloride bis(lithium chloride) complex; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With 3,3’-di-tert-butyl oxaziridine; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/jacs.6b12712

Reference yield: 77.0%

→ 3-amino-5-bromopyridine (13535-01-8)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.5h;

With 3,3’-di-tert-butyl oxaziridine; In tetrahydrofuran; at -78 ℃; for 0.166667h;

upstream raw materials:

3,5-dibromopyridine

5-bromonicotinamide

3-bromo-5-nitro-pyridine

3-Bromopyridine

Downstream raw materials:

5-bromo-3-ethoxypyridine

N-(5-bromo-pyridin-3-yl)-acetamide

3-bromo-5-fluoropyridine

3-bromo-5-iodopyridine

Refernces

• 1、 -. "Method for reducing aromatic nitro into arylamine". Paragraph 0185-0188. . Retrieved 2020/07/15.
• 2、 Zhou, Zhe,Ma, Zhiwei,Behnke, Nicole Erin,Gao, Hongyin,Kürti, László. "Non-deprotonative primary and secondary amination of (hetero)arylmetals". supporting information. p. 115 - 118. Retrieved 2017/05/16.