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754242

Tetrahydroxydiboron

95%

Synonym(s):

BBA, Bis-Boric acid, Diboronic acid

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250 mg
Please contact Customer Service for Availability
R 187.00
R 183.26
1 g
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R 654.00
R 640.92
5 g
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R 2,610.00
R 2,557.80
25 g
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R 4,860.00
R 4,762.80
100 g
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R 7,978.00
R 5,863.83

About This Item

Empirical Formula (Hill Notation):
B2H4O4
CAS Number:
Molecular Weight:
89.65
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:

R 183.26

List PriceR 187.00

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Quality Level

assay

95%

form

solid

mp

>385 °C

SMILES string

OB(O)B(O)O

InChI

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

InChI key

SKOWZLGOFVSKLB-UHFFFAOYSA-N

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This Item
499978P2000990795
assay

95%

assay

≥95%

assay

95%

assay

≥99.0% (T)

form

solid

form

-

form

crystals

form

liquid

mp

>385 °C

mp

256-260 °C (lit.)

mp

216-219 °C (lit.)

mp

−70 °C (lit.)

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

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.

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

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable


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Rapid and Selective in situ Reduction of Pyridine-N-oxides with Tetrahydroxydiboron.
Londregan A T
Synlett, 24(20), 2695-2700 (2013)
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)
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)

Related Content

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.

Global Trade Item Number

SKUGTIN
754242-1KG04061826735862
754242-100G04061833552186
754242-5G04061832907918
754242-250MG04061833339862
754242-25G04061833552193

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    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/418/501/product-dating-information-06-25-mk.pdf

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

    1 answer
    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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