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Home > Product > Heterocyclic Organic Compounds > 5-Bromo-2-fluoro-3-pyridylboronic acid

5-Bromo-2-fluoro-3-pyridylboronic acid | CAS Number: 501435-91-2

Catalog Number
ACM501435912
Product Name
5-Bromo-2-fluoro-3-pyridylboronic acid
Structure
CAS Number
501435-91-2
IUPAC Name
(5-bromo-2-fluoropyridin-3-yl)boronic acid
Synonyms
5-BROMO-2-FLUOROPYRIDINE-3-BORONIC ACID;5-BROMO-2-FLUOROPYRIDIN-3-YLBORONIC ACID;5-BROMO-2-FLUORO-3-PYRIDINEBORONIC ACID;(5-BROMO-2-FLUORO-3-PYRIDINYL)-BORONIC ACID;5-Bromo-2-fluoro-3-pyridylboronic acid;5-Bromo-2-Fluoropyridine-3-Bor;5-BROMO-2-FLUOROPYRI
Molecular Weight
219.8
Exact Mass
218.95000
Molecular Formula
C5H4BBrFNO2
Boiling Point
357.1ºC at 760 mmHg
Melting Point
>300ºC
Flash Point
169.7ºC
Density
1.86 g/cm33
Purity
98%
SMILES
B(C1=CC(=CN=C1F)Br)(O)O
InChIKey
YAXKWQSQZIVTFC-UHFFFAOYSA-N
H-Bond Donor
2
H-Bond Acceptor
4
Safty Description
S26-S36
Hazard Statements
Xi: Irritant;
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1Versatile synthesis of 3,5-disubstituted 2-fluoropyridines and 2-pyridones.

Sutherland A1, Gallagher T.

J Org Chem. 2003 Apr 18;68(8):3352-5.

5-bromo-2-fluoro-3-pyridylboronic acid (3) was prepared in high yield by ortho-lithiation of 5-bromo-2-fluoropyridine (1), followed by reaction with trimethylborate. Suzuki reaction of 3 with a range of aryl iodides gave 3-monosubstituted 5-bromo-2-fluoropyridines 4 in excellent yields. A second Suzuki reaction utilizing the bromo constituent of 4 with aryl and heteroaryl boronic acids provided 3,5-disubstituted 2-fluoropyridines 5, which in turn could be converted to the corresponding 2-pyridones 6.

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