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697095

Sigma-Aldrich

2-Chloropyridine-3-boronic acid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C5H5BClNO2
Numéro CAS:
381248-04-0
Poids moléculaire :
157.36
Numéro MDL:
MFCD03094997
Code UNSPSC :
12352103
ID de substance PubChem :
329761887
Nomenclature NACRES :
NA.22

Forme

powder

Pf

121-134 °C

Groupe fonctionnel

chloro

Température de stockage

2-8°C

Chaîne SMILES 

OB(O)c1cccnc1Cl

InChI

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

Clé InChI

VRDAOVQZVXYRNH-UHFFFAOYSA-N

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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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
MKBC0343V
MKBC0343
08915JJ

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Questions

1–7 sur 7 questions  

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

    1 réponse

    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.

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

    1 réponse

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

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  3. What compounds are formed when boronic acids degrade?

    1 réponse

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

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

    1 réponse

    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.

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

    1 réponse

    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.

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

    1 réponse

    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.

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

    1 réponse

    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.

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