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666459

Sigma-Aldrich

6-Indolylboronic acid

≥95%

Synonym(s):

6-Indoleboronic acid, Indole-6-boronic acid

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About This Item

Linear Formula:
(C8H6N)B(OH)2
CAS Number:
147621-18-9
Molecular Weight:
160.97
MDL number:
MFCD03095176
UNSPSC Code:
12352103
PubChem Substance ID:
24884798
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

mp

177-181 °C

storage temp.

2-8°C

SMILES string

OB(O)c1ccc2cc[nH]c2c1

InChI

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

InChI key

ZVMHOIWRCCZGPZ-UHFFFAOYSA-N

Application

Reactant involved in synthesis of:
  • Indole compounds for use as HIV-1 glycoprotein-41 fusion inhibitors
  • δ-Carbolines / carbozoles
  • Trisubstituted pyrimidines as PI3K inhibitors
  • (Thienopyridine)carboxamides as CHK1 inhibitors
  • cis-Fluorostilbenes

Reactant involved in Suzuki-Miyaura reactions
Used in a study of racemization in Suzuki cross-couplings of arylamino acids.

Other Notes

May contain varying amounts of anhydride

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
MKCQ5441
MKCC9869
MKBZ2885V
MKBN5427V
MKBD8458V

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Monica Prieto et al.
The Journal of organic chemistry, 72(3), 1047-1050 (2007-01-27)
Reaction conditions considered to be typical in Suzuki couplings can cause significant (up to 34% of the unwanted enantiomer) loss of optical purity in sensitive substrates such as hydroxyphenylglycine 1. This may be remedied using sodium succinate instead of sodium

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