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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:
MFCD13195770
UNSPSC Code:
12352103
PubChem Substance ID:
329764021
NACRES:
NA.23

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

Related Categories

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.

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 Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Triphenylamine-based dyes for dye-sensitized solar cells
Zhang F, et al.
Dyes and Pigments, 81(3), 224-230 (2009)
Base-promoted silver-catalyzed protodeboronation of arylboronic acids and esters
Liu C, et al.
Royal Society of Chemistry Advances, 5(20), 15354-15358 (2015)
New V-shaped push-pull systems based on 4, 5-di (hetero) aryl substituted pyrimidines: their synthesis and application to the detection of nitroaromatic explosives
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Microwave-assisted synthesis of 4-(2, 2'-bithiophen-5-yl)-5-phenylpyrimidine derivatives as sensors for detection of nitroaromatic explosives
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Chemistry of Heterocyclic Compounds, 52(11), 904-909 (2016)

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