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754242

Sigma-Aldrich

Tetrahydroxydiboron

95%

Synonyme(s) :

BBA, Bis-Boric acid, Diboronic acid

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About This Item

Formule empirique (notation de Hill) :
B2H4O4
Numéro CAS:
13675-18-8
Poids moléculaire :
89.65
Numéro MDL:
MFCD05663888
Code UNSPSC :
12352103
ID de substance PubChem :
329766409
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

95%

Forme

solid

Pf

>385 °C

Chaîne SMILES 

OB(O)B(O)O

InChI

1S/B2H4O4/c3-1(4)2(5)6/h3-6H

Clé InChI

SKOWZLGOFVSKLB-UHFFFAOYSA-N

Catégories apparentées

Application

Tetrahydroxydiboron (BBA) is an efficient borylating agent that can be used to borylate a wide variety of aryl and heteroaryl substrates with low Pd- and Ni-catalyst loads.[1][2]

Other reactions employing BBA as a reagent:
  • Palladium-catalyzed boronation of vinyl cyclopropane, vinyl aziridine, and allyl acetate substrates.[3]
  • To facilitate catalytic transfer hydrogenations of simple alkenes and alkynes.[4]
  • Selective reducing agent for in situ N-oxide reduction of pyridine-N-oxides.[5]
  • As a substitute to bis(pinacolato) diboron for Miyaura borylation.[6]

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H332,H315,H319,H335

Classification des risques

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF3072V
WXBF1535V
WXBF0277V
WXBD4875V
WXBD1357V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Rapid and Selective in situ Reduction of Pyridine-N-oxides with Tetrahydroxydiboron.
Londregan A T
Synlett, 24(20), 2695-2700 (2013)
Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/ Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid.
Molander GA, et al.
The Journal of Organic Chemistry, 77, 8678-8688 (2012)
Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid.
Molander GA, et al.
Journal of the American Chemical Society, 134, 11667-11673 (2012)
Palladium pincer complex catalyzed substitution of vinyl cyclopropanes, vinyl aziridines, and allyl acetates with tetrahydroxydiboron. An efficient route to functionalized allylboronic acids and potassium trifluoro (allyl) borates.
Sebelius S et al.
Journal of the American Chemical Society, 127(30), 10478-10479 (2005)
Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2 (OH) 4].
Molander G A, et al.
The Journal of Organic Chemistry, 78(13), 6427-6439 (2013)
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Contenu apparenté

Molander Group – Professor Product Portal

The central theme of the Molander group's research is the development of new synthetic methods and their application to the synthesis of organic molecules.

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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