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754242

Sigma-Aldrich

Tetrahydroxydiboron

95%

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Synonym(s):
BBA, Bis-Boric acid, Diboronic acid
Empirical Formula (Hill Notation):
B2H4O4
CAS Number:
Molecular Weight:
89.65
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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
P20009A71751499978
Tetrahydroxydiboron 95%

Sigma-Aldrich

754242

Tetrahydroxydiboron

Phenylboronic acid 95%

Sigma-Aldrich

P20009

Phenylboronic acid

form

solid

form

crystals

form

powder

form

-

mp

>385 °C

mp

216-219 °C (lit.)

mp

≥300 °C

mp

256-260 °C (lit.)

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

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

Signal Word

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Customers Also Viewed

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)
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)
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)

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