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518751

Sigma-Aldrich

4-Aminophenylboronic acid pinacol ester

97%

Synonym(s):

2-(4-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneamine, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine, 4-Aminophenylboronic acid, pinacol cyclic ester

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About This Item

Empirical Formula (Hill Notation):
C12H18BNO2
CAS Number:
214360-73-3
Molecular Weight:
219.09
MDL number:
MFCD02093721
UNSPSC Code:
12352103
PubChem Substance ID:
24874043
NACRES:
NA.22

Assay

97%

mp

165-169 °C (lit.)

SMILES string

CC1(C)OB(OC1(C)C)c2ccc(N)cc2

InChI

1S/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,14H2,1-4H3

InChI key

ZANPJXNYBVVNSD-UHFFFAOYSA-N

Application

4-Aminophenylboronic acid pinacol ester can be used as a reagent for:
  • The preparation of substituted 3-phenyl-4H-1-benzopyran-4-ones by reacting with iodochromones via Pd catalyzed Suzuki-Miyaura cross-coupling reaction.
  • Mercury(II) detection by fluorometry with new fluorogenic indicators based on through-bond energy transfer from pentaquinone to rhodamine.
  • Rhodium-catalyzed amination reactions.
  • Palladium-catalyzed Suzuki cross-coupling to synthesize potential antitubercular and antimicrobial compounds.

It can also be used to prepare:
  • Hexaphenylbenzene derivatives as a potential bioprobe and multichannel keypad system.
  • Pyromellitic diimide-based polymer as matrix for solution-processable n-channel field-effect transistors.
  • Alternating copolymers of oligoarylenes and naphthalene bisimides as low band-gap semiconductors with electrochemical and spectroelectrochemical behavior.
  • γ-secretase modulators in the treatment of amyloid β formation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior
Gawrys, P.; et al.
Electrochimica Acta, 56, 10464-10472 (2012)
Aminothiazoles as γ-secretase modulators
Luebbers, T.; et al.
Bioorganic & Medicinal Chemistry Letters, 21, 6554-6558 (2012)
Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors
Kola, S.; et al.
ACS Macro Letters, 1, 136-140 (2012)
Vandana Bhalla et al.
Organic letters, 14(4), 1012-1015 (2012-01-28)
Zinc ensemble of hexaphenylbenzene derivative 3 exhibits sensitive response toward adenosine monophosphate (AMP) and H(2)PO(4)(-) ions. Further, the application of derivative 3 as a multichannel molecular keypad could be realized in the presence of inputs of Zn(2+) ions, H(2)PO(4)(-) ions
Vandana Bhalla et al.
Inorganic chemistry, 51(4), 2150-2156 (2012-02-04)
New pentaquinone derivatives 5 and 8 having rhodamine moieties have been designed and synthesized that undergo through-bond energy transfer (TBET) in the presence of Hg(2+) ions among the various cations (Cu(2+), Pb(2+), Fe(2+), Fe(3+), Zn(2+), Ni(2+), Cd(2+), Co(2+), Ag(+), Ba(2+)
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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.

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