Benzeneboronic acid

• Catalog No.: A14257
• CAS Number: 98-80-6
• M. F.: C6H7BO2
• M. W.: 121.92958
• Purity: 98+%

SYNONYMS

• Title: 苯硼酸
• IUPAC name: phenylboronic acid
• IUPAC Traditional name: phenyl boronic acid
• Synonyms: Phenylboronic acid; Phenylboric acid

DATABASE IDS

• Merck Index: 141068
• MDL Number: MFCD00002103
• Beilstein Number: 970972
• EC Number: 202-701-9
• CAS Number: 98-80-6

PROPERTIES

• Purity: 98+%
• Melting Point: 214-219°C
• GHS Hazard statements: H302-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 22-36/37/38
• RTECS: CY8575000
• Safety Statements: 9-36/37
• Storage Warning: Hygroscopic
• TSCA Listed: 是

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.