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Tetrahydroxydiboron

Name: Tetrahydroxydiboron
Brand: ALDRICH

95%

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Synonym(s):

BBA, Bis-Boric acid, Diboronic acid

Empirical Formula (Hill Notation):

B₂H₄O₄

CAS Number:

13675-18-8

Molecular Weight:

89.65

MDL number:

MFCD05663888

PubChem Substance ID:

329766409

NACRES:

NA.22

Quality Level

200

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

Boronic Acids & Derivatives

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

GHS07

Signal Word

Warning

Hazard Statements

H302 + H332 - H315 - H319 - H335

Precautionary Statements

P261 - P264 - P301 + P312 - P302 + P352 - P304 + P340 + P312 - P305 + P351 + P338

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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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)

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)

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)

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)

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