[4-(diphenylamino)phenyl]boronic acid

• ChemBase ID: 142376
• Molecular Formular: C18H16BNO2
• Molecular Mass: 289.13614
• Monoisotopic Mass: 289.12740916
• SMILES: B(c1ccc(cc1)N(c1ccccc1)c1ccccc1)(O)O
• Canonical SMILES: OB(c1ccc(cc1)N(c1ccccc1)c1ccccc1)O
• InChI: InChI=1S/C18H16BNO2/c21-19(22)15-11-13-18(14-12-15)20(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14,21-22H
• InChIKey: TWWQCBRELPOMER-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(diphenylamino)phenyl]boronic acid
• IUPAC Traditional name: 4-(diphenylamino)phenylboronic acid
• Synonyms: 4-(N,N-Diphenylamino)-1-phenylboronic acid; 4-(N,N-Diphenylamino)phenylboronic acid; 4-(N-Diphenylamino)phenylboronic acid; 4-(Diphenylamino)benzeneboronic acid; Triphenylamine-4-boronic acid; 4-(Diphenylamino)phenylboronic acid; 4-Diphenylamino-phenylboronic acid; 4-硼酸三苯胺

Database IDs

• CAS Number: 201802-67-7
• MDL Number: MFCD06798117
• PubChem SID: 24883523; 162236606
• PubChem CID: 12166934

CALCULATED PROPERTIES

• Acid pKa: 8.944544
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.8194447
• LogD (pH = 7.4): 4.8074446
• Log P: 4.8196
• Molar Refractivity: 83.764 cm^3
• Polarizability: 33.892212 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 110-115 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C18H16BNO2

DETAILS

Sigma Aldrich - 647292

Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Strong multiphoton-excited blue photoluminescence and lasing from ladder-type oligo(p-phenylene)s1
• Suzuki coupling reactions2
• Ligand-free Suzuki reaction3Reagent used in Preparation of
• Push-pull arylvinyldiazine chromophores4
• Benzothiadiazole-based fluorophores contg. triphenylamine functionality5
• Blue light-emitting and hole-transporting materials for electroluminescent devices6
• p-quaterphenyls laterally substituted with dimesitylboryl group for use as solid-state blue emitters7
• Efficient sensitizers for dye-sensitized solar cells8,9
• Prange electroluminescent materials for single-layer white polymer OLEDs10
• Eeep-blue organic light emitting devices (OLEDs)11
• Ligands for Organic Photovoltaic cells12