[3-(dimethylamino)phenyl]boronic acid

• ChemBase ID: 12407
• Molecular Formular: C8H12BNO2
• Molecular Mass: 164.99738
• Monoisotopic Mass: 165.09610903
• SMILES: c1cc(cc(c1)B(O)O)N(C)C
• Canonical SMILES: OB(c1cccc(c1)N(C)C)O
• InChI: InChI=1S/C8H12BNO2/c1-10(2)8-5-3-4-7(6-8)9(11)12/h3-6,11-12H,1-2H3
• InChIKey: YZQQHZXHCXAJAV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(dimethylamino)phenyl]boronic acid
• IUPAC Traditional name: 3-(dimethylamino)phenylboronic acid
• Synonyms: 3-(N,N-Dimethylamino)phenylboronic acid; 3-(N,N-Dimethylamino)phenylboronic acid; 3-(Dimethylamino)benzeneboronic acid; 3-(N,N-二甲氨基)苯硼酸

Database IDs

• CAS Number: 178752-79-9
• MDL Number: MFCD01318996
• PubChem SID: 24885572; 160975714
• PubChem CID: 2762527

CALCULATED PROPERTIES

• Acid pKa: 8.780237
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.8972112
• LogD (pH = 7.4): 1.8864782
• Log P: 1.9042
• Molar Refractivity: 45.0321 cm^3
• Polarizability: 18.353842 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 178-190 °C; 178-190 °C

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95%; 97%; 98%
• Empirical Formula (Hill Notation): C8H12BNO2

DETAILS

Sigma Aldrich - 680532

General description
May contain varying amounts of anhydride
Packaging
1, 10 g in glass bottle
Application
Reactant involved in synthesis of different protein effector including:
• Modulators of survival motor neuron protein1
• Glucokinase activators2
• Aryl ethers for use as Bacillus anthracis enoyl-ACP reductase inhibitors3Reactant involved in synthesis of:
• Thiourea-functionalized paracyclophanes4
• Low-background fluorescent imaging agents for nitric oxide5Reactant to undergo regioselective iodination and bromination6