2-Bromo-5-fluoropyridine

Base Information

• Chemical Name: 2-Bromo-5-fluoropyridine
• CAS No.: 41404-58-4
• Molecular Formula: C5H3BrFN
• Molecular Weight: 175.988
• Hs Code.: 29333990
• European Community (EC) Number: 629-269-8
• DSSTox Substance ID: DTXSID70382481
• Nikkaji Number: J2.418.696B
• Wikidata: Q72456455
• Mol file: 41404-58-4.mol

Synonyms:2-Bromo-5-fluoropyridine;41404-58-4;2-Bromo-5-fluoro-pyridine;Pyridine, 2-bromo-5-fluoro-;3-Fluoro-6-bromopyridine;MFCD00234011;2-bromo5-fluoropyridine;2-bromo-5-fluoropyridin;2-bromo-5-fluorpyridine;2-bromo-5-fluropyridine;5-fluoro-2-bromopyridine;SCHEMBL102205;UODINHBLNPPDPD-UHFFFAOYSA-;DTXSID70382481;2-Bromo-5-fluoropyridine, 97%;UODINHBLNPPDPD-UHFFFAOYSA-N;BCP23362;BBL100812;RB1019;STL554606;AKOS005063981;CS-W008965;FG-0480;PB17160;AC-13898;SY004387;AM20051169;B2799;FT-0611487;EN300-53704;A927997;Q-103360;InChI=1/C5H3BrFN/c6-5-2-1-4(7)3-8-5/h1-3H

Chemical Property of 2-Bromo-5-fluoropyridine

Chemical Property:

• Appearance/Colour: light yellow cryst
• Vapor Pressure: 1.85mmHg at 25°C
• Melting Point: 30-31 °C(lit.)
• Refractive Index: 1.5396
• Boiling Point: 171.6 °C at 760 mmHg
• PKA: -1.63±0.10(Predicted)
• Flash Point: 57.6 °C
• PSA: 12.89000
• Density: 1.707 g/cm³
• LogP: 1.98320
• Storage Temp.: Store Cold
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 174.94329
• Heavy Atom Count: 8
• Complexity: 78.8

Purity/Quality:

99% ^*data from raw suppliers

5-Fluoropyridine-2-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn, F
• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-20/21/22-10
• Safety Statements: 26-36-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1F)Br
• Uses: 2-Bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain. 2-Bromo-5-fluoropyridine can be used in the synthesis of the following:5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid5-fluoro-2-(p-tolyl)pyridine via Suzuki coupling reaction with p-tolylboronic acidIt can undergo palladium-catalyzed homo-coupling reaction to give the corresponding biaryl. It can also be employed in a palladium-catayzed α-arylation of esters leading to 4-pyridylcarboxypiperidines.

Technology Process of 2-Bromo-5-fluoropyridine

There total 2 articles about 2-Bromo-5-fluoropyridine 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: 66.0%

2-amino-5-fluoropyridine (21717-96-4) → 2-bromo-5-fluoropyridine (41404-58-4)

Guidance literature:

2-amino-5-fluoropyridine; With hydrogen bromide; bromine; sodium nitrite; In water; at 0 - 5 ℃; for 1h;

With sodium hydroxide; In water; at 20 ℃; for 0.333333h;

Reference yield:

→ 2-bromo-5-fluoropyridine (41404-58-4)

Guidance literature:

5-Amino-2-bromopyridin, Aethylnitrit/HBF4;

DOI:10.1021/jo00927a002

Reference yield: 98.0%

2-bromo-5-fluoropyridine (41404-58-4) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → 4-(5-fluoropyridin-2-yl)-N,N-diphenylaniline (1263145-39-6)

Guidance literature:

With potassium phosphate tribasic heptahydrate; palladium diacetate; In water; isopropyl alcohol; at 80 ℃; for 0.2h;

DOI:10.1002/ejoc.201100072

upstream raw materials:

2-amino-5-fluoropyridine

Downstream raw materials:

ethyl 5-fluoro-2-pyridinecarboxylate

C₂₀H₁₅FN₂O

1-(5-fluoropyridin-2-yl)ethan-1-one

3-(5-(5-fluoro-pyridin-2-yl)-furan-2-yl)-benzonitrile

Refernces

• 1、 -. "IMIDAZOPYRIDINE COMPOUND". Page/Page column 35. . Retrieved 2008/06/13.
• 2、 Takeuchi, Kumiko,Holloway, William G.,McKinzie, Jamie H.,Suter, Todd M.,Statnick, Michael A.,Surface, Peggy L.,Emmerson, Paul J.,Thomas, Elizabeth M.,Siegel, Miles G.,Matt, James E.,Wolfe, Chad N.,Mitch, Charles H.. "Structure-activity relationship studies of carboxamido-biaryl ethers as opioid receptor antagonists (OpRAs). Part 1". . p. 5349 - 5352. Retrieved 2008/02/13.