Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

697095

Sigma-Aldrich

2-Chloropyridine-3-boronic acid

Synonym(s):

(2-Chloro-3-pyridyl)boronic acid, (2-Chloropyridin-3-yl)boronic acid, Dihydroxy(2-chloro-3-pyridyl)borane

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C5H5BClNO2
CAS Number:
381248-04-0
Molecular Weight:
157.36
MDL number:
MFCD03094997
UNSPSC Code:
12352103
PubChem Substance ID:
329761887
NACRES:
NA.22

form

powder

mp

121-134 °C

functional group

chloro

storage temp.

2-8°C

SMILES string

OB(O)c1cccnc1Cl

InChI

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

InChI key

VRDAOVQZVXYRNH-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

May contain varying amounts of anhydride
Reactant for:
  • Synthesis of Et canthinone-3-carboxylates from Et 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-catalyzed Suzuki-Miyaura coupling and a Cu-catalyzed amidation reaction
  • Preparation of arylmethylpyrrolidinylmethanols and amine derivatives via reaction with MIDA followed by Suzuki reaction with halides or amination with amines
  • Preparation of arylazabicyclooctane derivatives as potential arginine vasopressin receptor antagonists
  • Regioselective preparation of halo-oligopyridines and oligopyridines by the Suzuki-Miyaura cross-coupling reaction

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBC0343V
MKBC0343
08915JJ

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Questions

1–7 of 7 Questions  

  1. How can you determine if boronic acid anhydride is present? And if it is found to be present, how do you remove it?

    1 answer

    1. Typically anhydride formation may be detected when the inside drying flask temperature increases abnormally, color change, or free flowing solid looks wet. To remove the anhydrides, charge de-oxygenated deionized (DI) water to the flask, and make slurry. Filter under nitrogen pressure, and use more de-oxygenated DI water for rinsing the solids. Then wash the solids with a solvent the product is insoluble in. Finally, dry the product with moist nitrogen.

      Helpful?

  2. What is it about boronic acids that makes them acidic?

    1 answer

    1. Boronic acids have a vacant p orbital. Therefore, despite the presence of two hydroxyl groups, the acidic character of most Boronic acids is that of a Lewis acid.

      Helpful?

  3. How does the storage temperature relate to shipping conditions?

    1 answer

    1. The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.

      Helpful?

  4. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  5. What compounds are formed when boronic acids degrade?

    1 answer

    1. Boronic acids are typically very stable. However, if degradation occurs, Boronic acid will degrade to corresponding alcohol and boric acid.

      Helpful?

  6. What is the pKa of Product 697095, 2-Chloropyridine-3-boronic acid?

    1 answer

    1. The pKa of most boronic acids is approximately 9.

      Helpful?

  7. What is the solubility for Product 697095, 2-Chloropyridine-3-boronic acid?

    1 answer

    1. Unfortunately, we do not test the solubility for this product. However, a similar product (Product No. 634492) is soluble in THF at 25 mg/mL, and is very insoluble in DMSO.

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service