pyridine; triethenyl-1,3,5,2,4,6-trioxatriborinane

• ChemBase ID: 91517
• Molecular Formular: C11H14B3NO3
• Molecular Mass: 240.66676
• Monoisotopic Mass: 241.12528451
• SMILES: B1(OB(C=C)OB(O1)C=C)C=C.n1ccccc1
• Canonical SMILES: c1cccnc1.C=CB1OB(C=C)OB(O1)C=C
• InChI: InChI=1S/C6H9B3O3.C5H5N/c1-4-7-10-8(5-2)12-9(6-3)11-7;1-2-4-6-5-3-1/h4-6H,1-3H2;1-5H
• InChIKey: YLHJACXHRQQNQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine; triethenyl-1,3,5,2,4,6-trioxatriborinane
• IUPAC Traditional name: pyridine; triethenyl-1,3,5,2,4,6-trioxatriborinane
• Synonyms: Cyclic vinylboronic anhydride trimer pyridine complex; O'Shea's reagent; Trivinylboroxin pyridine complex; Triethenylboroxin pyridine complex; 2,4,6-Trivinylcyclotriboroxane pyridine complex 95%; Trivinyl-boroxin pyridine complex; Trivinylcyclotriboroxane pyridine complex; 2,4,6-Trivinylcyclotriboroxane pyridine complex; Vinylboronic anhydride pyridine complex; 2,4,6-三乙烯基环硼氧烷吡啶络合物; 乙烯硼酐吡啶络合物

Database IDs

• CAS Number: 95010-17-6; 442850-89-7
• MDL Number: MFCD03839940
• PubChem SID: 24882902; 162078216
• PubChem CID: 2734806

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.4333
• LogD (pH = 7.4): 2.4333
• Log P: 2.4333
• Molar Refractivity: 67.7916 cm^3
• Polarizability: 17.546059 Å^3
• Polar Surface Area: 39.42 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 44-52°C; 44-52°C
• Boiling Point: 78-80°C
• Flash Point: 176 °F; 80 °C; 80°C

Safety Information

• Storage Warning: Flammable/Irritant/Moisture Sensitive/Store at -20oC/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H319
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C6H9B3O3 · C5H5N

DETAILS

Sigma Aldrich - 637998

Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura cross-coupling1,2
• Stereoselective synthesis via Palladium-catalyzed carboamination3
• Alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent to cytosine base in RNA4
• Kaiser oxime resin-derived palladacycle as a recoverable polymeric precatalyst in Suzuki-Miyaura cross-coupling reactions in aqueous media5
• Kinetic resolution of phosphoryl and sulfonyl esters of binaphthol derivatives via Pd-catalyzed alcoholysis of their vinyl ethers6
• Stereoselective isomerization of N-allyl aziridines into Z-enamines by using rhodium hydride catalysis7
• Kinetic resolution of axially chiral biaryl derivatives via palladium/chiral diamine ligand-catalyzed alcoholysis8
• Transition metal-catalyzed alkenylation of aziridines, cycloaddition and thermal rearrangement reactions9
• Intramolecular Heck reaction strategy for synthesis of functionalized tetrahydroanthracenes10 Reagent used for Preparation of
• BACE-1 inhibitors and SAR of cyclic sulfone hydroxyethylamines11
• Distorted spiropentanes1
• Small molecule bradykinin B2 receptor antagonists in angioedema therapy12
• Enol Ethers13
• Styryl cyclobutanone

REFERENCES

• Stable equivalent of the readily-polymerizable vinylboronic acid, first reported by Matteson: J. Org. Chem., 27, 3712 (1962), and more recently adopted by O'Shea as a vinylboron unit for Suzuki cross-coupling reactions with aryl halides to give substituted styrenes: J. Org. Chem., 67, 4968 (2002). The reaction has been applied to the formation of ortho-Boc-amino styrenes, further reaction of which has been developed as a route to diversely functionalized indoles: J. Am. Chem. Soc., 125, 4054 (2003). Copper(II) acetate mediated coupling with phenols affords an efficient synthesis of aryl vinyl ethers: J. Org. Chem., 69, 5087 (2004).