phenylboronic acid

• ChemBase ID: 1566
• Molecular Formular: C6H7BO2
• Molecular Mass: 121.92958
• Monoisotopic Mass: 122.05390986
• SMILES: OB(O)c1ccccc1
• Canonical SMILES: OB(c1ccccc1)O
• InChI: InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
• InChIKey: HXITXNWTGFUOAU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenylboronic acid
• IUPAC Traditional name: phenyl boronic acid
• Synonyms: Dihydroxyphenylborane; NSC 66487; Phenyl-boric acid; Phenyldihydroxyborane; Phenylboronic acid; Benzeneboronic acid; Phenylboronic acid; Phenyl Boronic Acid; PHENYLBORIC ACID; Benzeneboronic acid; Phenylboric acid; Phenylboronic acid; Benzeneboronic acid; 苯硼酸; 苯基硼酸; 苯硼酸

Database IDs

• CAS Number: 98-80-6
• EC Number: 202-701-9
• MDL Number: MFCD00002103
• Beilstein Number: 970972
• Merck Index: 141068
• PubChem SID: 46508036; 160965023; 24898261; 24887271
• PubChem CID: 66827
• CHEBI ID: 44923
• CHEMBL: 21485
• Chemspider ID: 60191
• DrugBank ID: DB01795
• Wikipedia Title: Phenylboronic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.759042
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.6395621
• LogD (pH = 7.4): 1.6213038
• Log P: 1.6398
• Molar Refractivity: 30.6035 cm^3
• Polarizability: 13.532594 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.53
• LOG S: -1.08
• Solubility (Water): 1.01e+01 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 g/mL in MeOH in water
• Apperance: white powder
• Melting Point: 214-216°C; 214-219°C; 216-219 °C(lit.); 216-219°C; 216-219 °C; 218-222 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Harmful/Irritant/Hygroscopic/Store under Argon/Keep Cold; Hygroscopic; IRRITANT, MOISTURE SENSITIVE
• RTECS: CY8575000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 22-36/37/38; R:22
• Safety Statements: 22-24/25; 9-36/37; S:36/37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302-H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (HPLC); 95%; 97%; 98%; 98+%
• Grade: purum
• Linear Formula: C6H5B(OH)2

DETAILS

MP Biomedicals - 05206684

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156164

Crystalline

MP Biomedicals - 05217356

MP Biomedicals Rare Chemical collection

DrugBank - DB01795

Drug information: experimental

Sigma Aldrich - 78181

Other Notes
Contains varying amounts of phenylboronic anhydride
Application
Reagent used for
• Rhodium-catalyzed intramolecular amination1
• Pd-catalyzed direct arylation2
• Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles3
• Palladium-catalyzed stereoselective Heck-type reaction4
• Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water5 Reagent used in Preparation of
• Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions6,7
• N-type polymers for all-polymer solar cells8
• Novel series of potent and selective mTOR kinase inhibitors9
• Inhibitors of lactate dehydrogenase against cancer cell proliferation10

Sigma Aldrich - P20009

Other Notes
Contains varying amounts of phenylboronic anhydride
Packaging
10, 50, 250 g in poly bottle
Application
Reagent used for
• Rhodium-catalyzed intramolecular amination1
• Pd-catalyzed direct arylation2
• Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles3
• Palladium-catalyzed stereoselective Heck-type reaction4
• Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water5 Reagent used in Preparation of
• Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions6,7
• N-type polymers for all-polymer solar cells8
• Novel series of potent and selective mTOR kinase inhibitors9
• Inhibitors of lactate dehydrogenase against cancer cell proliferation10

REFERENCES

• Reagent for protection of diols as their cyclic boronates: J. Am. Chem. Soc., 80, 2443 (1958); Tetrahedron, 25, 477 (1969), which are also useful in GC and GC-MS. This has been utilized to trap cis-diols, in order to prevent over-oxidation during dihydroxylation reactions catalyzed by Osmium(VIII) oxide, 12103: Chem. Lett., 1721 (1988); J. Org. Chem., 63, 7322 (1998).
• Promotes the ortho-hydroxalkylation of phenols by aldehydes. The cyclic boronate, formed via a [3,3] sigmatropic rearrangement, is the key intermediate: Synthesis, 365 (1979):
  
• With citronellal, hexahydrocannabinoids are formed: J. Chem. Soc., Perkin 1, 605 (1992).
• Acts as a template for Diels-Alder reactions, by forming boronate linkages with a hydroxydiene and a hydroxydienophile: Synthesis 1171 (1991); for Nicolaou's application to synthesis of the CD ring system of taxol, see: J. Chem. Soc., Chem. Commun., 1118 (1992); J. Am. Chem. Soc., 117, 634 (1995):
  
• For use in the formation of an oxazaborolidine catalyst for use in enantioselective reductions, see note under (S)-(-)-ɑ,ɑ-Diphenylprolinol, L09217.
• Forms a stable chiral acyloxyborane (CAB) catalyst with tartaric acid derivatives, which catalyze hetero Diels-Alder reactions, e.g. between aldehydes and 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L06100, to give enantioselectively, dihydro-4-pyrone derivatives: Tetrahedron, 50, 979 (1994).
• The most widely-used reaction of arylboronic acids is the Pd-catalyzed Suzuki synthesis of unsymmetrical biaryls: Synth. Commun., 11, 513 (1981):
  
• For illustrative example, see: Org. Synth., 75, 53 (1997).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 2679 (2006). For further information and reviews on boronic acid chemistry, see Appendix 5.