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666467

Sigma-Aldrich

5-Indolylboronic acid

≥95%

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Synonym(s):
5-Indoleboronic acid, Indole-5-boronic acid
Linear Formula:
(C8H6N)B(OH)2
CAS Number:
Molecular Weight:
160.97
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
675911666491680516
vibrant-m

666467

5-Indolylboronic acid

vibrant-m

675911

N-Boc-indole-2-boronic acid

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

form

solid

form

solid

form

solid

form

solid

mp

170-175 °C

mp

84-94 °C, 85-90 °C (lit.)

mp

113-117 °C

mp

102-107 °C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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

signalword

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

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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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