3-Bromo-2,5-dichloropyridine

Base Information

• Chemical Name: 3-Bromo-2,5-dichloropyridine
• CAS No.: 138006-41-4
• Molecular Formula: C5H2BrCl2N
• Molecular Weight: 226.888
• Hs Code.: 2933399090
• European Community (EC) Number: 678-681-4
• DSSTox Substance ID: DTXSID20512574
• Nikkaji Number: J463.302D
• Wikidata: Q72465822
• Mol file: 138006-41-4.mol

Synonyms:3-Bromo-2,5-dichloropyridine;138006-41-4;3-bromo-2,5-dichloro-pyridine;PYRIDINE, 3-BROMO-2,5-DICHLORO-;MFCD06659484;SCHEMBL899507;3-bromo-2, 5-dichloropyridine;3-bromo-2.5-dichloro-pyridine;DTXSID20512574;CDBHWRZEXFQNBI-UHFFFAOYSA-N;BCP22191;AC-895;AKOS015851186;3-Bromo-2 pound not5-dichloropyridine;AB25941;CS-W003322;AS-14935;SY022285;3-Bromo-2,5-dichloropyridine, AldrichCPR;A2974;AM20061724;B4832;FT-0654888;EN300-175311;J-511833

Chemical Property of 3-Bromo-2,5-dichloropyridine

Chemical Property:

• Appearance/Colour: White or cream-colored powder
• Vapor Pressure: 0.0634mmHg at 25°C
• Melting Point: 38-40 °C
• Refractive Index: 1,424-1,426
• Boiling Point: 239 °C at 760mmHg
• PKA: -3.02±0.10(Predicted)
• Flash Point: 98.3 °C
• PSA: 12.89000
• Density: 1.848 g/cm³
• LogP: 3.15090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 224.87477
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-2,5-dichloropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-41-37/38-25
• Safety Statements: 26-45-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1Br)Cl)Cl

Technology Process of 3-Bromo-2,5-dichloropyridine

There total 2 articles about 3-Bromo-2,5-dichloropyridine 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: 59.0%

2-amino-3-bromo-5-chloropyridine (26163-03-1) → 3-bromo-2,5-dichloropyridine (138006-41-4)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at -20 - 20 ℃; for 4h;

DOI:10.1021/acs.joc.6b00413

Reference yield:

3-bromo-5-chloropyridine N-oxide (1221793-62-9) → 5-bromo-2,3-dichloropyridine (97966-00-2) + 3-bromo-2,5-dichloropyridine (138006-41-4)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; at -70 ℃; for 0.5h; Overall yield = 74.9 %; Overall yield = 340 mg; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01057

Reference yield: 85.0%

3-bromo-2,5-dichloropyridine (138006-41-4) + 4-methanesulphonylphenylboronic acid (149104-88-1) → 2,5-dichloro-3-[4-(methylsulfonyl)phenyl]pyridine (202409-86-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; water; toluene; at 110 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jacs.8b09595

upstream raw materials:

2-amino-3-bromo-5-chloropyridine

3-bromo-5-chloropyridine N-oxide

Downstream raw materials:

N-tert-Butyl-4-(2,5-dichloro-pyridin-3-yl)-benzenesulfonamide

2-(benzyloxy)-3-bromo-5-chloropyridine

2,5-dichloro-3-[4-(methylsulfonyl)phenyl]pyridine

Refernces

• 1、 Hwang, Tsang-Lin,Bartberger, Michael D.,Chen, Ying. "Application of 1,1-ADEQUATE, HMBC, and Density Functional Theory to Determine Regioselectivity in the Halogenation of Pyridine N-Oxides". . p. 1956 - 1959. Retrieved 2016/06/01.
• 2、 Murtiashaw, Charles W.,Breitenbach, Ralph,Goldstein, Steven W.,Pezullo, Susan L.,Quallich, George J.,Sarges, Reinhard. "2,3-Pyridine Annulation. The Enantioselective Synthesis of an Aldose Reductase Inhibitor". . p. 1930 - 1933. Retrieved 2007/10/02.