(1H-indol-6-yl)boronic acid

• ChemBase ID: 16352
• Molecular Formular: C8H8BNO2
• Molecular Mass: 160.96562
• Monoisotopic Mass: 161.0648089
• SMILES: [nH]1ccc2ccc(cc12)B(O)O
• Canonical SMILES: OB(c1ccc2c(c1)[nH]cc2)O
• InChI: InChI=1S/C8H8BNO2/c11-9(12)7-2-1-6-3-4-10-8(6)5-7/h1-5,10-12H
• InChIKey: ZVMHOIWRCCZGPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1H-indol-6-yl)boronic acid
• IUPAC Traditional name: 1H-indol-6-ylboronic acid
• Synonyms: 6-Borono-1H-indole; 1H-Indole-6-boronic acid 98%; Indole-6-boronic acid; 6-Indoleboronic acid; Indole-6-boronic acid; 6-Indolylboronic acid; 6-Boronoindole; Indole-6-boronic acid; 6-吲哚基硼酸; 吲哚-6-硼酸; 6-吲哚硼酸; 吲哚-6-硼酸

Database IDs

• CAS Number: 147621-18-9
• MDL Number: MFCD03095176
• PubChem SID: 160979659; 24884798
• PubChem CID: 2763205

CALCULATED PROPERTIES

• Acid pKa: 8.700382
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 1.7409278
• LogD (pH = 7.4): 1.7200922
• Log P: 1.7412
• Molar Refractivity: 41.69 cm^3
• Polarizability: 18.764753 Å^3
• Polar Surface Area: 56.25 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 168-170°C; 177-181 °C; 177-181°C

Safety Information

• Storage Warning: Air Sensitive; IRRITANT; Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Linear Formula: (C8H6N)B(OH)2

DETAILS

Sigma Aldrich - 666459

Application
Used in a study of racemization in Suzuki cross-couplings of arylamino acids.7
Reactant involved in synthesis of:
• Indole compounds for use as HIV-1 glycoprotein-41 fusion inhibitors1
• δ-Carbolines / carbozoles2
• Trisubstituted pyrimidines as PI3K inhibitors3
• (Thienopyridine)carboxamides as CHK1 inhibitors4
• cis-Fluorostilbenes5Reactant involved in Suzuki-Miyaura reactions6
Other Notes
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle