754242

Sigma-Aldrich

Tetrahydroxydiboron

95%

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

Quality Level

assay

95%

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

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.

Packaging

1 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Target Organs

Respiratory system

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Rapid and Selective in situ Reduction of Pyridine-N-oxides with Tetrahydroxydiboron.
Londregan A T
Synlett, 24(20), 2695-2700 (2013)
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)
Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.
Molander G A, et al.
Journal of the American Chemical Society, 132(50), 17701-17703 (2010)
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)
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.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.