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574686

Sigma-Aldrich

3-Aminophenylboronic acid pinacol ester

97%

Synonym(s):

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

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About This Item

Empirical Formula (Hill Notation):
C12H18BNO2
CAS Number:
Molecular Weight:
219.09
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

Quality Level

assay

97%

mp

90-94 °C (lit.)

SMILES string

CC1(C)OB(OC1(C)C)c2cccc(N)c2

InChI

1S/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-6-5-7-10(14)8-9/h5-8H,14H2,1-4H3

InChI key

YMXIIVIQLHYKOT-UHFFFAOYSA-N

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This Item
576557578401574694
mp

90-94 °C (lit.)

mp

63-68 °C (lit.)

mp

78-82 °C (lit.)

mp

206-210 °C (lit.)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

3-Aminophenylboronic acid pinacol ester can be used:
  • As a starting material for the synthesis of 6-(hetero)arylthieno[3,2-b]pyridines, which are known to inhibit human tumor cells selectively.[1]
  • In the functionalization of deuteroporphyrin IX dimethyl ester through Suzuki-Miyaura coupling.[2]
  • To prepare benzo[d]oxazole based type-I FLT3-ITD inhibitors.[3]

Legal Information

Product of Boron Molecular

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Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Functionalization of Deutero-and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactions
O?Brien JM, et al.
The Journal of Organic Chemistry, 84(10), 6158-6173 (2019)
Efficient synthesis of 6-(hetero) arylthieno [3, 2-b] pyridines by Suzuki-Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle
Queiroz M-J, et al.
European Journal of Medicinal Chemistry, 45(12), 5628-5634 (2010)
Discovery of benzo [d] oxazole derivatives as the potent type-I FLT3-ITD inhibitors
Bao J, et al.
Bioorganic Chemistry, 94(10), 103248-103248 (2020)

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