[4-(dimethylamino)phenyl]boronic acid

• ChemBase ID: 10035
• Molecular Formular: C8H12BNO2
• Molecular Mass: 164.99738
• Monoisotopic Mass: 165.09610903
• SMILES: c1c(ccc(c1)B(O)O)N(C)C
• Canonical SMILES: OB(c1ccc(cc1)N(C)C)O
• InChI: InChI=1S/C8H12BNO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6,11-12H,1-2H3
• InChIKey: RIIPFHVHLXPMHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(dimethylamino)phenyl]boronic acid
• IUPAC Traditional name: 4-(dimethylamino)phenylboronic acid
• Synonyms: 4-(Dimethylamino)benzeneboronic acid; 4-(N,N-Dimethylamino)phenylboronic acid; 4-(N,N-Dimethylamino)phenylboronic acid; 4-N,N-Dimethylaminobenzeneboronic acid; 4-N,N-Dimethylphenylboronic acid; 4-Dimethylaminobenzeneboronic acid; p-(Dimethylamino)-benzeneboronic acid; [4-(Dimethylamino)phenyl-1-yl]boronic acid; [4-(Dimethylamino)phenyl]boric acid; 4-(Dimethylamino)phenylboronic acid; 4-(DIMETHYLAMINO)PHENYLBORONIC ACID; 4-(二甲基氨基)苯硼酸

Database IDs

• CAS Number: 28611-39-4
• MDL Number: MFCD01074642
• PubChem SID: 160973342; 24871900
• PubChem CID: 2734344

CALCULATED PROPERTIES

• Acid pKa: 9.090736
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9016163
• LogD (pH = 7.4): 1.8954519
• Log P: 1.9042
• Molar Refractivity: 45.0321 cm^3
• Polarizability: 18.353317 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 227 °C(lit.)

Safety Information

• Storage Warning: Irritant; IRRITANT, AIR SENSITIVE, KEEP COLD
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥95.0%; 97%; 98%
• Linear Formula: (CH3)2NC6H4B(OH)2

DETAILS

Sigma Aldrich - 483532

Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura cross-coupling reaction1
• Nickel (Ni)-catalyzed Suzuki-Miyaura cross-coupling2
• Rhodium (Rh)-catalyzed asymmetric addition reactions3
• Palladium (Pd)-catalyzed C-OH bond activation4 Reagent used in Preparation of
• Push-pull arylvinyldiazine chromophores5
• Helical ortho-phenylene oligomers with terminal push-pull substitution6
• Alginate-supported cation-Pd nanoparticle gels as catalysts for the Suzuki-Miyaura cross-coupling reaction7
• Organic dyes for dye-sensitized solar cells1