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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM2095
SHBK3920
SHBF9681V
SHBB9479V
02496BP

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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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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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