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522554

Sigma-Aldrich

2-Hydroxyphenylboronic acid pinacol ester

98%

Synonym(s):

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

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About This Item

Empirical Formula (Hill Notation):
C12H17BO3
CAS Number:
269409-97-4
Molecular Weight:
220.07
MDL number:
MFCD02093754
UNSPSC Code:
12352103
PubChem Substance ID:
24874280
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.506 (lit.)

bp

282 °C (lit.)

density

1.05 g/mL at 25 °C (lit.)

SMILES string

CC1(C)OB(OC1(C)C)c2ccccc2O

InChI

1S/C12H17BO3/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8,14H,1-4H3

InChI key

VLROJECCXBBKPZ-UHFFFAOYSA-N

Application

Reactant involved in:
  • Synthesis of indolo-fused heterocyclic inhibitors of polymerase enzyme of hepatitis C
  • Studies of pi-interactions, electronic structure and transient UV absorption of subphthalocyanine-borate-bridged ferrocene-fullerene conjugates
  • Synthesis of subphthalocyanine and fused-ring nicotine derivatives
  • Suzuki-Miyaura coupling-triflation sequence, reduction and salt formation for synthesis of hydroxylated oligoarene phosphines
Widely used in Suzuki coupling chemistry.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Tetrahedron, 58, 9633-9695 (2002)

Articles

Arylboronic Acid-Pinacol Esters

The synthesis of biaryl compounds via the Suzuki coupling reaction has become more commonplace now that many arylboronic acids are readily available. We are pleased to offer arylboronic acid pinacol esters4 as part of a growing line of products used in the Suzuki coupling reaction.

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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