(3-{[(tert-butoxy)carbonyl]amino}phenyl)boronic acid

• ChemBase ID: 64090
• Molecular Formular: C11H16BNO4
• Molecular Mass: 237.06004
• Monoisotopic Mass: 237.1172384
• SMILES: C(=O)(Nc1cc(B(O)O)ccc1)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)Nc1cccc(c1)B(O)O
• InChI: InChI=1S/C11H16BNO4/c1-11(2,3)17-10(14)13-9-6-4-5-8(7-9)12(15)16/h4-7,15-16H,1-3H3,(H,13,14)
• InChIKey: CWLNHPXWZRALFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-{[(tert-butoxy)carbonyl]amino}phenyl)boronic acid
• IUPAC Traditional name: 3-[(tert-butoxycarbonyl)amino]phenylboronic acid
• Synonyms: 3-(Boc-amino)phenylboronic acid; 3-[(tert-Butoxycarbonyl)amino]phenylboronic acid; 3-(Boc-amino)benzeneboronic acid; 3-[(tert-Butoxycarbonyl)amino]benzeneboronic acid; 3-Boronoaniline, N-BOC protected; 3-Aminobenzeneboronic acid, N-BOC protected; 3-(N-Boc-Amino)phenylboronic acid; 3-(N-Boc-amino)phenylboronic acid; (3-BOC-AMINOPHENYL)BORONIC ACID; 3-(Boc-氨基)苯硼酸; 3-(N-Boc-氨基)苯硼酸

Database IDs

• CAS Number: 380430-68-2
• MDL Number: MFCD03411945
• PubChem SID: 24880955; 162029829
• PubChem CID: 2773228

CALCULATED PROPERTIES

• Acid pKa: 8.67048
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.4241085
• LogD (pH = 7.4): 2.4018266
• Log P: 2.4244
• Molar Refractivity: 60.8957 cm^3
• Polarizability: 24.644478 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 160-170°C; 168 °C (dec.)(lit.); ca 155°C dec.

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• 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

Product Information

• Purity: ≥95%; 95%; 97%; 98%
• Linear Formula: (CH3)3CO2CNHC6H4B(OH)2

DETAILS

Sigma Aldrich - 578851

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Rhodium-catalyzed cross-coupling1
• Pd-catalyzed Suzuki-Miyaura coupling2,3