triphenyl borate

• ChemBase ID: 151615
• Molecular Formular: C18H15BO3
• Molecular Mass: 290.1209
• Monoisotopic Mass: 290.11142474
• SMILES: B(Oc1ccccc1)(Oc1ccccc1)Oc1ccccc1
• Canonical SMILES: c1ccc(cc1)OB(Oc1ccccc1)Oc1ccccc1
• InChI: InChI=1S/C18H15BO3/c1-4-10-16(11-5-1)20-19(21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15H
• InChIKey: MDCWDBMBZLORER-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl borate
• IUPAC Traditional name: boric acid, triphenyl ester
• Synonyms: NSC 806; Triphenoxyborane; Triphenyl ester boric acid; Triphenyl borate; Boron Triphenoxide; Triphenoxyboron; Triphenyl Borate; Boric Acid Triphenyl Ester; Phenyl Borate; 三苯基硼酸酯

Database IDs

• CAS Number: 1095-03-0
• EC Number: 214-137-0
• MDL Number: MFCD00059011
• PubChem SID: 162245766; 24866237
• PubChem CID: 14182

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 6.7202
• LogD (pH = 7.4): 6.7202
• Log P: 6.7202
• Molar Refractivity: 80.4735 cm^3
• Polarizability: 33.564007 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: <95°C; 98-101 °C(lit.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS: ED5775000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-41
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301 + H311 + H331-H318
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P2 (EN 143) respirator cartridges, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 95+%
• Linear Formula: (C6H5O)3B

DETAILS

Sigma Aldrich - 418714

Packaging
10 g in glass bottle
Application
Catalyst involved in:
• Multicomponent aziridination of aldehydes1
• Hetero-Diels-Alder reactions and Mukaiyama aldol condensation2
• Cross-metathesis of alkenes with 3-nitropropene3
• Asymmetric Claisen rearrangement of unactivated allyl vinyl ethers4
• Ethoxylation5
• Asymmetric aziridination of imines6

Toronto Research Chemicals - T808800

An organoborane compound with chemosterilant activity against Cochliomyia hominivorax (screwworm flies). A competitive inhibitor of urease of Klebsiella aerogenes used to study the mechanisms of interaction with the nickel active site.

REFERENCES

• Settepani, J.A. et al.: J. Econ. Entomol., 63, 375 (1969)
• Todd, M.J. et al.: J. Biol. Chem., 264, 15835 (1969)