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Merck
CN

723614

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

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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

SMILES string

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

InChI key

VKSWIFGDKIEVFZ-UHFFFAOYSA-N

assay

95%

form

powder

mp

93-98 °C

Quality Level

100

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7854
MKBS5025V
MKBN4574V
MKBH2811V

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Microwave-assisted synthesis of 4-(2, 2'-bithiophen-5-yl)-5-phenylpyrimidine derivatives as sensors for detection of nitroaromatic explosives
Verbitskiy EV, et al.
Chemistry of Heterocyclic Compounds, 52(11), 904-909 (2016)
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
Verbitskiy EV, et al.
ARKIVOC (Gainesville, FL, United States), 3(11), 360-373 (2016)
Base-promoted silver-catalyzed protodeboronation of arylboronic acids and esters
Liu C, et al.
Royal Society of Chemistry Advances, 5(20), 15354-15358 (2015)
Triphenylamine-based dyes for dye-sensitized solar cells
Zhang F, et al.
Dyes and Pigments, 81(3), 224-230 (2009)
Fluorine in Life Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals
Progress in Fluorine Science Series (2018)

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