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Sigma-Aldrich

Tetrahydroxydiboron

95%

Synonyme(s) :

BBA, Bis-Boric acid, Diboronic acid

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250 MG
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1 G
40.00 CHF
5 G
146.00 CHF
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568.00 CHF
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1 090.00 CHF
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250 MG
10.60 CHF
1 G
40.00 CHF
5 G
146.00 CHF
25 G
568.00 CHF
100 G
1 090.00 CHF
1 KG
5 620.00 CHF

About This Item

Formule empirique (notation de Hill) :
B2H4O4
Numéro CAS:
Poids moléculaire :
89.65
Numéro MDL:
Code UNSPSC :
12352103
ID de substance PubChem :
Nomenclature NACRES :
NA.22

10.60 CHF


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Niveau de qualité

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

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

Mention d'avertissement

Warning

Mentions de danger

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)

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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)
Development and Scale-up of an Efficient Miyaura Borylation Process Using Tetrahydroxydiboron.
Gurung S R, et al.
Organic Process Research & Development, 21(1), 65-74 (2016)
Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor.
Cummings S P, et al.
Journal of the American Chemical Society, 138(19), 6107-6110 (2016)

Contenu apparenté

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.

Questions

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  1. 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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    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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