754242
Tetrahydroxydiboron
95%
Synonym(s):
BBA, Bis-Boric acid, Diboronic acid
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About This Item
Empirical Formula (Hill Notation):
B2H4O4
CAS Number:
Molecular Weight:
89.65
MDL number:
UNSPSC Code:
12352103
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
Related Categories
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:
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Certificates of Analysis (COA)
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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)
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)
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)
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