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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
Pricing and availability is not currently available.

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.[1]
  • Mercury(II) detection by fluorometry with new fluorogenic indicators based on through-bond energy transfer from pentaquinone to rhodamine.[2]
  • Rhodium-catalyzed amination reactions.[3]
  • Palladium-catalyzed Suzuki cross-coupling to synthesize potential antitubercular and antimicrobial compounds.[4]

It can also be used to prepare:
  • Hexaphenylbenzene derivatives as a potential bioprobe and multichannel keypad system.[5]
  • Pyromellitic diimide-based polymer as matrix for solution-processable n-channel field-effect transistors.[6]
  • Alternating copolymers of oligoarylenes and naphthalene bisimides as low band-gap semiconductors with electrochemical and spectroelectrochemical behavior.[7]
  • γ-secretase modulators in the treatment of amyloid β formation.[8]

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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Michael König et al.
Tetrahedron, 67(23), 4243-4252 (2011-07-16)
The palladium-catalyzed Suzuki-Miyaura cross-coupling reaction has been investigated on meso-substituted trans-A(2)B-corrole using tailored Pd-catalyst systems.We present the first examples of Suzuki-Miyaura cross-coupling reactions on meso-substituted trans-A(2)B-corrole derivatives with neutral, sterically hindered, inactivated and heteroaromatic boronic acids and esters, alkenylboronic acids
David A Vasselin et al.
Journal of medicinal chemistry, 49(13), 3973-3981 (2006-06-23)
A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones and isoflavones (quercetin and genistein respectively) and antitumor 2-phenylbenzothiazoles. Target compounds were synthesized using palladium-catalyzed coupling methodologies
Synthesis of potential antitubercular and antimicrobial s-triazine-based scaffolds via Suzuki cross-coupling reaction
Patel, A. B.; et al.
Medicinal Chemistry Research (2012)
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+)
Aminothiazoles as γ-secretase modulators
Luebbers, T.; et al.
Bioorganic & Medicinal Chemistry Letters, 21, 6554-6558 (2012)
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      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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