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95010-17-6 molecular structure
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pyridine; triethenyl-1,3,5,2,4,6-trioxatriborinane

ChemBase ID: 91517
Molecular Formular: C11H14B3NO3
Molecular Mass: 240.66676
Monoisotopic Mass: 241.12528451
SMILES and InChIs

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

Cite this record

CBID:91517 http://www.chembase.cn/molecule-91517.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
95010-17-6
442850-89-7
MDL Number
MFCD03839940
PubChem SID
24882902
162078216
PubChem CID
2734806

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 2734806 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 2.4333  LogD (pH = 7.4) 2.4333 
Log P 2.4333  Molar Refractivity 67.7916 cm3
Polarizability 17.546059 Å3 Polar Surface Area 39.42 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
44-52°C expand Show data source
44-52°C expand Show data source
Boiling Point
78-80°C expand Show data source
Flash Point
176 °F expand Show data source
80 °C expand Show data source
80°C expand Show data source
Storage Warning
Flammable/Irritant/Moisture Sensitive/Store at -20oC/Store under Argon expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36 expand Show data source
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
H319 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
95% expand Show data source
Empirical Formula (Hill Notation)
C6H9B3O3 · C5H5N expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 637998 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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