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637998 Sigma-Aldrich

Vinylboronic anhydride pyridine complex

95%

Synonym: 2,4,6-Trivinylcyclotriboroxane pyridine complex, Trivinyl-boroxin pyridine complex, Trivinylcyclotriboroxane pyridine complex

  • CAS Number 442850-89-7

  • Empirical Formula (Hill Notation) C6H9B3O3 · C5H5N

  • Molecular Weight 240.67

  •  MDL number MFCD03839940

  •  PubChem Substance ID 24882902

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Properties

Related Categories Alkenyl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents More...
InChI Key   YLHJACXHRQQNQR-UHFFFAOYSA-N
assay   95%
storage temp.   −20°C

Description

Application

Reagent used for
• Suzuki-Miyaura cross-coupling
• Stereoselective synthesis via Palladium-catalyzed carboamination
• Alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent to cytosine base in RNA
• Kaiser oxime resin-derived palladacycle as a recoverable polymeric precatalyst in Suzuki-Miyaura cross-coupling reactions in aqueous media
• Kinetic resolution of phosphoryl and sulfonyl esters of binaphthol derivatives via Pd-catalyzed alcoholysis of their vinyl ethers
• Stereoselective isomerization of N-allyl aziridines into Z-enamines by using rhodium hydride catalysis
• Kinetic resolution of axially chiral biaryl derivatives via palladium/chiral diamine ligand-catalyzed alcoholysis
• Transition metal-catalyzed alkenylation of aziridines, cycloaddition and thermal rearrangement reactions
• Intramolecular Heck reaction strategy for synthesis of functionalized tetrahydroanthracenes

Reagent used for Preparation of
• BACE-1 inhibitors and SAR of cyclic sulfone hydroxyethylamines
• Distorted spiropentanes
• Small molecule bradykinin B2 receptor antagonists in angioedema therapy
• Enol Ethers
• Styryl cyclobutanone

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
176 °F
Flash Point(C) 
80 °C

Documents

Certificate of Analysis

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Protocols & Articles

Articles

Boronic Acids - ChemFiles 2007

Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of boronic acids may contain varying amounts of this cyclic anhydride. Fortunately, the aci...
ChemFiles 2007, 7.7, 3.
Keywords: Coupling reactions, Dehydration reaction, Suzuki coupling

Peer-Reviewed Papers
15

References

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