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H28703 Vinylboronic anhydride pyridine complex, 95%

CAS Number
95010-17-6
Synonyms
O'Shea's reagent
Trivinylboroxin pyridine complex

Stock No. Size Price ($) Quantity Availability
H28703-03 1g 53.50
H28703-06 5g 165.00
H28703-14 25g 718.00
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Vinylboronic anhydride pyridine complex, 95%

MDL
MFCD03839940

Chemical Properties

Formula
C6H9B3O3
Formula Weight
161.57
Melting point
44-52°
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Store under Nitrogen.
Solubility
Soluble in methanol.

Applications

Reagent used for Suzuki-Miyaura cross-coupling, stereoselective synthesis via Palladium-catalyzed carboamination, Alkyl-connected 2-amino-6-vinylpurine (AVP) cross linking 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 and Kinetic resolution of phosphoryl and sulfonyl esters of binaphthol derivatives via Pd-catalyzed alcoholysis of their vinyl ethers.

Notes

Moisture Sensitive, store away from water/moisture. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store under dry inert gas.

Literature References

Kuan-Jen Su; Jean-Luc Mieusset; Vladimir B Arion; Wolfgang Knoll; Lothar Brecker; Udo H Brinker. Efforts toward distorted spiropentanes. Journal of Organic Chemistry. 2010, 75(21), 7494-7497.

Amanda F Ward; and John P Wolfe. Stereoselective synthesis of substituted 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols.Organic Letters. 2011, 13(17), 4728-4731.

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H228-H302-H312-H315-H319-H332-H335

Flammable solid. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation.

Precautionary Statements: P210-P240-P241-P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Hazard Class
4.1
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
No

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