3-Amino-2-bromo-5-chloropyridine

Base Information

• Chemical Name: 3-Amino-2-bromo-5-chloropyridine
• CAS No.: 90902-83-3
• Molecular Formula: C5H4BrClN2
• Molecular Weight: 207.457
• Hs Code.: 2933399090
• European Community (EC) Number: 674-547-4
• DSSTox Substance ID: DTXSID30377813
• Nikkaji Number: J3.099.116H
• Wikidata: Q72451387
• Mol file: 90902-83-3.mol

Synonyms:3-AMINO-2-BROMO-5-CHLOROPYRIDINE;90902-83-3;2-bromo-5-chloropyridin-3-amine;2-Bromo-3-Amino-5-Chloropyridine;3-Pyridinamine, 2-bromo-5-chloro-;MFCD07368976;2-bromo-5-chloro-pyridin-3-amine;SCHEMBL305370;DTXSID30377813;AZOXQBMBDRLSCQ-UHFFFAOYSA-N;2-Bromo-5-chloropyridine-3-amine;2-Bromo-5-chloro-pyridin-3-ylamine;AKOS015855685;DS-0697;SB78492;AC-24911;SY033433;TS-02963;AM20061830;CS-0042741;FT-0649790;3-amino-2-bromo-5-chloropyridine, AldrichCPR;EN300-208882;J-508350;3-Amino-2-bromo-5-chloropyridine

Chemical Property of 3-Amino-2-bromo-5-chloropyridine

Chemical Property:

• Vapor Pressure: 0.00052mmHg at 25°C
• Melting Point: 141-143 °C
• Refractive Index: 1.648
• Boiling Point: 312.7 °C at 760 mmHg
• PKA: -0.54±0.10(Predicted)
• Flash Point: 142.9 °C
• PSA: 38.91000
• Density: 1.834 g/cm³
• LogP: 2.66090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 205.92464
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-5-chloro-3-pyridinamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1N)Br)Cl
• Uses: 2-Bromo-5-chloro-3-pyridinamine is a reactant in the synthetic preparation of Chloro(chloromethyl)thiazolopyridine, a precursor of PC190723 (an antibacterial cell division inhibitor)

Technology Process of 3-Amino-2-bromo-5-chloropyridine

There total 3 articles about 3-Amino-2-bromo-5-chloropyridine 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: 97.7%

2-bromo-5-chloro-3-nitropyridine (75806-86-9) → 3-amino-2-bromo-5-chloropyridine (90902-83-3)

Guidance literature:

With iron; acetic acid; at 60 ℃;

DOI:10.1080/00397911.2011.566408

Reference yield:

5-chloro-2-pyridylamine (1072-98-6) → 3-amino-2-bromo-5-chloropyridine (90902-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid; nitric acid / 1 h / 55 - 59 °C

2: hydrogen bromide; bromine; sodium nitrite / water / 0.75 h / -5 - 0 °C

3: iron; acetic acid / 60 °C

With sulfuric acid; hydrogen bromide; bromine; nitric acid; iron; acetic acid; sodium nitrite; In water;

DOI:10.1080/00397911.2011.566408

Reference yield:

5-chloro-3-nitropyridin-2-ol (21427-61-2) → 3-amino-2-bromo-5-chloropyridine (90902-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine; phosphorus (III)-bromide

2: iron-turnings; acetic acid

With bromine; phosphorus tribromide; iron; acetic acid;

upstream raw materials:

2-bromo-5-chloro-3-nitropyridine

5-chloro-3-nitropyridin-2-ol

5-chloro-2-pyridylamine

Downstream raw materials:

3-amino-2,5-dichloropyridine

3-amino-5-chloropicolinonitrile

N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide

N-(2-bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide

Refernces

• 1、 Ding, Zi-Chun,Ma, Xiang,Zhou, Weicheng. "Convenient and practical synthesis of 6-chloro-2-(chloromethyl)- thiazolo[5,4-b]pyridine". experimental part. p. 2791 - 2796. Retrieved 2012/07/28.