(3,5-dichlorophenyl)boronic acid

• ChemBase ID: 10575
• Molecular Formular: C6H5BCl2O2
• Molecular Mass: 190.8197
• Monoisotopic Mass: 189.97596516
• SMILES: c1(cc(cc(c1)B(O)O)Cl)Cl
• Canonical SMILES: OB(c1cc(Cl)cc(c1)Cl)O
• InChI: InChI=1S/C6H5BCl2O2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,10-11H
• InChIKey: DKYRKAIKWFHQHM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3,5-dichlorophenyl)boronic acid
• IUPAC Traditional name: 3,5-dichlorophenylboronic acid
• Synonyms: 3,5-Dichlorobenzeneboronic acid; 3,5-Dichlorobenzeneboronic acid solution; (3,5-dichlorophenyl)boranediol; (3,5-Dichlorophenyl)dihydroxyborane; 3,5-Dichlorobenzeneboronic acid; 3,5-Dichlorophenylboronic acid; 3,5-Dichlorophenylboronic acid; 3,5-Dichlorophenylboronic acid; 3,5-Dichlorobenzeneboronic acid; 3,5-二氯苯硼酸 溶液; 3,5-二氯苯硼酸

Database IDs

• CAS Number: 67492-50-6
• MDL Number: MFCD00051935
• Beilstein Number: 7581091
• PubChem SID: 24868166; 160973882
• PubChem CID: 2734331

CALCULATED PROPERTIES

• Acid pKa: 8.551282
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6754162
• LogD (pH = 7.4): 2.646334
• Log P: 2.6758
• Molar Refractivity: 40.2131 cm^3
• Polarizability: 17.345398 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 322 - 324°C; ca 315°C(dec); ca 315°C dec.
• Hydrophobicity(logP): 3.021

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• UN Number: 2056
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 2056 3/PG 2

Product Information

• Purity: 95%; 97%; 98%; 98+%
• Concentration: 50 wt. % in THF/water (90:10)
• Linear Formula: Cl2C6H3B(OH)2
• Empirical Formula (Hill Notation): C6H5BCl2O2

DETAILS

Sigma Aldrich - 445207

Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura cross-coupling1,2
• Trifluoromethylation3
• Intramolecular aromatic carbenoid insertion of biaryldiazoacetates4
• Cyanation for the synthesis of aromatic nitriles5
• Lithiation of dihalophenyl dioxazaborocines for synthesis of functionalized dihalophenyl boronic acid6

REFERENCES

• Reagent for derivatization of diols and diamines for GC: Chromatographia, 11, 347 (1978). For reactions of boronic acids, see Appendix 5.