Description

Dibutyl Vinylboronate (stabilized with Phenothiazine) is a highly specialized organoboron compound with the molecular formula C₁₀H₂₁BO₂ and CAS number 6336-45-4. This reagent is stabilized with phenothiazine to enhance its shelf life and handling safety. It is widely utilized in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, where it serves as a versatile vinylboron precursor. The compound is characterized by its clear to pale yellow liquid appearance and must be stored under inert conditions to prevent degradation. Ideal for researchers and chemists, this high-purity reagent is packaged under nitrogen to ensure optimal stability and performance in sensitive applications.

Properties

• CAS Number: 6336-45-4
• Complexity: 107
• IUPAC Name: dibutoxy(vinyl)borane
• InChI: InChI=1S/C10H21BO2/c1-4-7-9-12-11(6-3)13-10-8-5-2/h6H,3-5,7-10H2,1-2H3
• InChI Key: JQKJEPJLCSCBGW-UHFFFAOYSA-N
• Exact Mass: 184.1634601
• Molecular Formula: C10H21BO2
• Molecular Weight: 184.09
• SMILES: B(C=C)(OCCCC)OCCCC
• Topological: 18.5
• Monoisotopic Mass: 184.1634601
• Synonyms: Dibutyl Vinylboronate (stabilized with Phenothiazine), 663-504-5, Vinylboronic acid dibutyl ester, 6336-45-4, dibutyl vinylboronate, dibutoxy(ethenyl)borane, Boronic acid, ethenyl-, dibutyl ester, vinylboronic acid dibutylester, Dibutoxyvinylborane, Etheneboronic acid, dibutyl ester, MFCD00050049, di-n-butyl vinylboronate, SCHEMBL403419, DTXSID00284808, vinyl-boronic acid di-butyl ester, NSC39124, NSC-39124, AKOS015839710, Vinylboronic acid dibutyl ester, 97%, AB02106, AS-47007, 96% +(GC)(stabilized with Phenothiazine), VINYLBORONIC ACID DIBUTYL ESTER 97, CS-0069732, D3596, 10.14272/JQKJEPJLCSCBGW-UHFFFAOYSA-N, F11358, DibutylVinylboronate(stabilizedwithPhenothiazine), doi:10.14272/JQKJEPJLCSCBGW-UHFFFAOYSA-N, InChI=1/C10H21BO2/c1-4-7-9-12-11(6-3)13-10-8-5-2/h6H,3-5,7-10H2,1-2H

Application

Dibutyl Vinylboronate is a key reagent in Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex organic syntheses. It is particularly valuable in pharmaceutical research for constructing vinyl-substituted aromatic systems. Additionally, it finds use in material science for developing advanced polymers and functionalized materials. Its stabilization with phenothiazine ensures reliable performance in air-sensitive reactions.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.5%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.