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518786

Sigma-Aldrich

4-Hydroxy-3-methoxyphenylboronic acid pinacol ester

98%

Synonym(s):

2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 4-Hydroxy-3-methoxyphenylboronic acid, pinacol cyclic ester

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About This Item

Empirical Formula (Hill Notation):
C13H19BO4
CAS Number:
269410-22-2
Molecular Weight:
250.10
MDL number:
MFCD02093723
UNSPSC Code:
12352103
PubChem Substance ID:
24874046
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

105-109 °C (lit.)

SMILES string

COc1cc(ccc1O)B2OC(C)(C)C(C)(C)O2

InChI

1S/C13H19BO4/c1-12(2)13(3,4)18-14(17-12)9-6-7-10(15)11(8-9)16-5/h6-8,15H,1-5H3

InChI key

WFSJROCEOJANPD-UHFFFAOYSA-N

Application

4-Hydroxy-3-methoxyphenylboronic acid pinacol ester can be used as a reactant:
  • In the Suzuki-Miyaura cross-coupling reaction.
  • To prepare ethylidenedihydroindolones as potential neoplastic agents.
  • To synthesize 5,6-dihydropyrrolo[2,1-b]isoquinoline derivatives, which can be utilized as scaffolds to prepare lamellarin analogs via regioselective bromination and Suzuki cross-coupling reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBW5725V
MKBW5743V
MKBW1673V
MKBS1999V
MKBL5335V

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New oxidative labels for electrochemical detection of DNA
Simonova A, et al.
Collection of Czechoslovak Chemical Communications, 14, 365-366 (2015)
Synthesis and biological evaluation of 3-ethylidene-1, 3-dihydro-indol-2-ones as novel checkpoint 1 inhibitors
L Nan-Horng, et al.
Bioorganic & Medicinal Chemistry Letters, 16(2), 421-426 (2006)
5, 6-Dihydropyrrolo [2, 1-b] isoquinolines as scaffolds for synthesis of lamellarin analogues
Olsen CA, et al.
Tetrahedron Letters, 46(12), 2041-2044 (2005)

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