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Merck

723614

Sigma-Aldrich

4-(Diphenylamino)phenylboronic acid pinacol ester

95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H26BNO2
Molecular Weight:
371.28
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

Pricing and availability is not currently available.

Quality Level

Assay

95%

form

powder

mp

93-98 °C

SMILES string

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

General 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.[1][2]

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.[3][4] It can also be used in the synthesis of oligothiophene (electron donating group) for the fabrication of dye sensitized solar cells (DSSCs).[5]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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