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721034

Sigma-Aldrich

5-Chloro-3-pyridineboronic acid

≥95%

Synonym(s):

(3-Chloro-5-pyridyl)boronic acid, (3-Chloropyridin-5-yl)boronic acid, (5-Chloropyridin-3-yl)boronic acid, 3-Chloropyridine-5-boronic acid, 5-Chloropyridine-3-boronic acid

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About This Item

Empirical Formula (Hill Notation):
C5H5BClNO2
CAS Number:
872041-85-5
Molecular Weight:
157.36
MDL number:
MFCD06798243
UNSPSC Code:
12352103
PubChem Substance ID:
329763814
NACRES:
NA.22

Assay

≥95%

form

solid

mp

255-260 °C

storage temp.

2-8°C

SMILES string

OB(O)c1cncc(Cl)c1

InChI

1S/C5H5BClNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H

InChI key

NJXYBTMCTZAUEE-UHFFFAOYSA-N

Application

5-Chloro-3-pyridineboronic acid can be used as an intermediate:
  • In the preparation of positron emission tomography (PET) radioligand [11C]MK-1064, which is applicable in the orexin-2 receptor imaging.
  • In the synthesis of orexin 2 receptor antagonist (2-SORA) MK-1064.
  • In the preparation of pyridyl-cycloalkyl derived microsomal prostaglandin E synthase-1 inhibitors.
  • In the synthesis of ATAD2 bromodomain inhibitors.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of [11C] MK-1064 as a new PET radioligand for imaging of orexin-2 receptor
Gao M, et al.
Bioorganic & Medicinal Chemistry Letters, 26(15), 3694-3699 (2016)
Discovery of 5″-Chloro-N-[(5,6-dimethoxypyridin-2-yl) methyl]-2, 2′: 5′, 3″-terpyridine-3′-carboxamide (MK-1064): A Selective Orexin 2 Receptor Antagonist (2-SORA) for the Treatment of Insomnia
Roecker AJ, et al.
ChemMedChem, 9(2), 311-322 (2014)
Fragment-based discovery of low-micromolar ATAD2 bromodomain inhibitors
Demont EH, et al.
Journal of Medicinal Chemistry, 58(14), 5649-5673 (2015)
Discovery and optimization of pyridyl-cycloalkyl-carboxylic acids as inhibitors of microsomal prostaglandin E synthase-1 for the treatment of endometriosis
Koppitz M, et al.
Bioorganic & Medicinal Chemistry Letters, 29(18), 2700-2705 (2019)

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