4-(Diphenylamino)phenylboronic acid pinacol ester

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4-(Diphenylamino)phenylboronic acid pinacol ester

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Catalog Number

ACMA00016287

Product Name

4-(Diphenylamino)phenylboronic acid pinacol ester

Structure

Category

Synthetic Tools and Reagents

Synonyms

Diphenyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine, N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-N-phenylbenzenamine

Description

4-(Diphenylamino)phenylboronic acid pinacol ester is an aryl boronic acid ester that is majorly used in organic synthesis. It can be used in the transition metal-catalyzed Suzuki-Miyaura cross-coupling reaction due to its low toxicity and unique reactivity. It is an electron rich boronic acid ester that can also be used in protodeboronation.

IUPAC Name

N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Molecular Weight

371.28

Molecular Formula

C24H26BNO2

Canonical SMILES

CC1(C)OB(OC1(C)C)c2ccc(cc2)N(c3ccccc3)c4ccccc4

InChI

1S/C24H26BNO2/c1-23(2)24(3,4)28-25(27-23)19-15-17-22(18-16-19)26(20-11-7-5-8-12-20)21-13-9-6-10-14-21/h5-18H,1-4H3

InChI Key

VKSWIFGDKIEVFZ-UHFFFAOYSA-N

Melting Point

93-98 °C

Application

4-(Diphenylamino)phenylboronic acid pinacol ester may be used to synthesize 4-(2,2' -bithiophen-5-yl)- 5-phenylpyrimidine for potential usage in the development of sensing devices for the detection of nitroaromatic explosives. It can also be used in the synthesis of oligothiophene (electron donating group) for the fabrication of dye sensitized solar cells (DSSCs).

Storage

room temp

Complexity

469

Covalently-Bonded Unit Count

Exact Mass

371.205659g/mol

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Formal Charge

Heavy Atom Count

MDL Number