2-Amino-5-bromopyridine

Base Information

• Chemical Name: 2-Amino-5-bromopyridine
• CAS No.: 1072-97-5
• Molecular Formula: C5H5BrN2
• Molecular Weight: 173.012
• Hs Code.: 29333999
• European Community (EC) Number: 214-019-9
• NSC Number: 26282
• UNII: D5QE8XW52U
• DSSTox Substance ID: DTXSID5022144
• Nikkaji Number: J31.389K
• Wikipedia: 2-amino-5-bromopyridine
• Wikidata: Q27276127
• Mol file: 1072-97-5.mol

Synonyms:2-amino-5-bromopyridine

Chemical Property of 2-Amino-5-bromopyridine

Chemical Property:

• Appearance/Colour: Light yellow crystal
• Vapor Pressure: 0.0643mmHg at 25°C
• Melting Point: 135-138 °C
• Refractive Index: 1.5182 (estimate)
• Boiling Point: 230.9 °C at 760 mmHg
• PKA: 4.65±0.13(Predicted)
• Flash Point: 93.4 °C
• PSA: 38.91000
• Density: 1.71 g/cm³
• LogP: 2.00750
• Storage Temp.: Store below +30°C.
• Water Solubility.: Soluble in methanol, chloroform, ethyl acetate. Slightly soluble in water.
• XLogP3: 1.2
• 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:

98.00% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=NC=C1Br)N
• Uses: 2-Amino-5-bromopyridine is used for the synthesis of polycyclic azaarenes.

Technology Process of 2-Amino-5-bromopyridine

There total 28 articles about 2-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: 98.0%

2-aminopyridine (504-29-0) → 5-bromo-2-pyridylamine (1072-97-5)

Guidance literature:

With N-Bromosuccinimide; In acetone; at 0 - 20 ℃;

Reference yield: 96.0%

5-bromo2-nitropyridine (39856-50-3) → 5-bromo-2-pyridylamine (1072-97-5)

Guidance literature:

With tetrahydroxydiboron; 5%-palladium/activated carbon; water; In acetonitrile; at 50 ℃; for 24h;

DOI:10.1016/j.tet.2017.05.056

Reference yield: 90.0%

2-aminopyridine (504-29-0) → 5-bromo-2-pyridylamine (1072-97-5) + 2-amino-3,5-dibromopyridine (35486-42-1)

Guidance literature:

With tetra-N-butylammonium tribromide; In chloroform; at 20 ℃; for 0.0333333h; other reagent: tetraphenylphosphonium tribromide;

upstream raw materials:

2-aminopyridine

5-bromo2-nitropyridine

pyridinium N-<2'-(5'-bromopyridyl)>aminide

5-bromo-2-nitraminopyridine

Downstream raw materials:

N-(5-bromo-[2]pyridyl)-mandelamide

5-bromo-N-ethylpyridin-2-amine

2-amino-6-bromo[1,3]thiazolo[4,5-b]pyridine

7- bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Refernces

• 1、 Gomez-Garcia, Omar,Salgado-Zamora, Hector,Campos-Aldrete, Elena. "Tertiary formylated amines by microwave irradiation of N,N-dimethyl- N′-(2-pyridyl) formamidines with methyl vinyl ketone". . p. 21 - 23. Retrieved 2014.
• 2、 Alekseyev, Roman S.,Amirova, Sabina R.,Terenin, Vladimir I.. "Preparation of 2,3-Disubstituted 5-Bromo-1 H -pyrrolo[2,3- b ]pyridine Framework by Fischer Cyclization". . p. 3169 - 3178. Retrieved 2015.
• 3、 Jagadeesh, Rajenahally V.,Natte, Kishore,Junge, Henrik,Beller, Matthias. "Nitrogen-doped graphene-activated iron-oxide-based nanocatalysts for selective transfer hydrogenation of nitroarenes". . p. 1526 - 1529. Retrieved 2015.
• 4、 Agosti, Alessandro,Bertolini, Giorgio,Bruno, Giacomo,Lautz, Christian,Glarner, Thomas,Deichtmann, Walter. "Handling Hydrogen Peroxide Oxidations on a Large Scale: Synthesis of 5-Bromo-2-nitropyridine". . p. 451 - 459. Retrieved 2017.
• 5、 Burgos,Delgado,Garcia-Navio,Izquierdo,Alvarez-Builla. "Halogenation of pyridinium-N-(2'-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines". . p. 8649 - 8654. Retrieved 1995.
• 6、 Canibano,Rodriguez,Santos,Sanz-Tejedor,Carreno,Gonzalez,Garcia-Ruano. "Mild regioselective halogenation of activated pyridines with N-bromosuccinimide". . p. 2175 - 2179. Retrieved 2001.
• 7、 Jin, Jun,Lin, Yan,Liu, Yunyun,Wan, Jie-Ping,Wang, Chaoli. "Electrochemical C-H Halogenations of Enaminones and Electron-Rich Arenes with Sodium Halide (NaX) as Halogen Source for the Synthesis of 3-Halochromones and Haloarenes". . p. 12378 - 12385. Retrieved 2021/09/07.
• 8、 -. "Synthetic method of medicinal raw material 2 and 5 - dibromopyridine". Paragraph 0018; 0021; 0024. . Retrieved 2021/10/05.