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666467

Sigma-Aldrich

5-Indolylboronic acid

≥95%

Synonym(s):

5-Indoleboronic acid, Indole-5-boronic acid

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About This Item

Linear Formula:
(C8H6N)B(OH)2
CAS Number:
144104-59-6
Molecular Weight:
160.97
MDL number:
MFCD01319013
UNSPSC Code:
12352103
PubChem Substance ID:
24884799
NACRES:
NA.22

Assay

≥95%

form

solid

mp

170-175 °C

storage temp.

2-8°C

SMILES string

OB(O)c1ccc2[nH]ccc2c1

InChI

1S/C8H8BNO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10-12H

InChI key

VHADYSUJZAPXOW-UHFFFAOYSA-N

General description

May contain varying amounts of anhydride

Application

Reactant involved in the synthesis of biologically active molecules including:
  • Indole inhibitors of MMP-13 for arthritic disease treatment
  • Substituted pyrimidines acting as tubulin polymerization inhibitors

Reactant involved in Suzuki coupling reactions for synthesis of
  • Aryl- hetarylfurocoumarins
  • Aryl-substituted oxabenzindoles and methanobenzindoles

Reactant involved in:
  • Oxidative cross-coupling with mercaptoacetylenes
  • Trifluoromethylation
Substrate used in a rhodium-catalyzed 1,4-addition to unprotected maleimides.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM7454
MKCD0169
MKBT3484V
MKBN5098V
MKBJ2527V

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Tetrahedron Letters, 48, 4413-4413 (2007)
Haluk Dinçalp et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 202, 196-206 (2018-05-23)
Five isoindigo-based donor-acceptor-donor (D-A-D) type small molecules have been synthesized in order to investigate their intramolecular charge transfer characteristics. UV-vis absorption of these dyes exhibits a wide absorption band ranging from 300 to 650 nm with two distinct bands, giving the

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