{1-[(tert-butoxy)carbonyl]-1H-indol-2-yl}boronic acid

• ChemBase ID: 10579
• Molecular Formular: C13H16BNO4
• Molecular Mass: 261.08144
• Monoisotopic Mass: 261.1172384
• SMILES: c1ccc2c(c1)n(c(c2)B(O)O)C(=O)OC(C)(C)C
• Canonical SMILES: OB(c1cc2c(n1C(=O)OC(C)(C)C)cccc2)O
• InChI: InChI=1S/C13H16BNO4/c1-13(2,3)19-12(16)15-10-7-5-4-6-9(10)8-11(15)14(17)18/h4-8,17-18H,1-3H3
• InChIKey: SVIBPSNFXYUOFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {1-[(tert-butoxy)carbonyl]-1H-indol-2-yl}boronic acid
• IUPAC Traditional name: 1-(tert-butoxycarbonyl)indol-2-ylboronic acid
• Synonyms: 1-(tert-butoxycarbonyl)indole-2-boronic acid; N-(tert-butoxycarbonyl)indole-2-boronic acid; N-Boc-indole-2-boronic acid; N-(tert-Butoxycarbonyl)-1H-indole-2-boronic acid; 1H-Indole-2-boronic acid, N-BOC protected 98%; 1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid; 1-(tert-Butoxycarbonyl)indole-2-boronic acid; 1-Boc-indole-2-boronic acid; 1-(叔丁氧基羰基)吲哚-2-硼酸; N-(叔丁氧基羰基)吲哚-2-硼酸; 1-Boc-吲哚-2-硼酸

Database IDs

• CAS Number: 1001162-89-5; 213318-44-6
• MDL Number: MFCD02093045
• Beilstein Number: 8148683
• PubChem SID: 24885308; 160973886
• PubChem CID: 2773302

CALCULATED PROPERTIES

• Acid pKa: 8.204823
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.6676486
• LogD (pH = 7.4): 2.6055791
• Log P: 2.6685
• Molar Refractivity: 65.6428 cm^3
• Polarizability: 28.697025 Å^3
• Polar Surface Area: 71.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 84-94 °C; 85-90 °C(lit.); ca 85°C dec.

Safety Information

• Storage Warning: IRRITANT; IrritantKeep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%; 95%; 97%; 98%
• Empirical Formula (Hill Notation): C13H16BNO4

DETAILS

Sigma Aldrich - 675911

Application
Used in a synthesis of hydroxyquinones via Suzuki-Miyaura coupling of phenylidonium ylides of hydroxyquinones.6
Reactant involved in:
• Suzuki-Miyaura cross-coupling reactions1,2
• Copper-catalyzed trifluoromethylation3
• Palladium-catalyzed benzylation4
• Homocoupling reactions5
General description
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle