1190375-91-7

Basic information

• Product Name: N,N-dimethyl-4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]aniline
• Synonyms: N,N-dimethyl-4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]aniline
• CAS NO: 1190375-91-7
• Molecular Weight: 273.183
• Mol File: 1190375-91-7.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: N,N-dimethyl-4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]aniline(1190375-91-7)
• EPA Substance Registry System: N,N-dimethyl-4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]aniline(1190375-91-7)

Safety Data

• Hazardous Substances Data: 1190375-91-7(Hazardous Substances Data)

Upstream product

• 35283-06-8 3-(4-(dimethylamino)phenyl)propiolic acid 
• 73183-34-3 bis(pinacol)diborane 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 75927-49-0 pinacol vinylboronate 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 
• 2124-31-4 4'-dimethylaminoacetophenone 
• 92146-68-4 4-(2-methoxyethenyl)-N,N-dimethylaniline 
• 2039-80-7 N,N-dimethy-4-vinylaniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 586-77-6 4-bromo-N,N-dimethylaniline 

Downstream Products

• 1266052-57-6 C₁₀H₁₂IN 

Relevant articles and documents

Lithium compounds as single site catalysts for hydroboration of alkenes and alkynes

The hydroboration of alkenes and alkynes using easily accessible lithium compounds [2,6-di-tert-butyl phenolatelithium (1a) and 1,1′ dilithioferrocene (1b)] has been achieved with good yields, high functional group tolerance and excellent chemoselectivity

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.

Two-Photon Sensitive Coumarinyl Photoremovable Protecting Groups with Rigid Electron-Rich Cycles Obtained by Domino Reactions Initiated by a 5- exo-Dig Cyclocarbopalladation

We herein report the design, synthesis, and photophysical characterization of extended and rigid coumarinyl derivatives showing large two-photon sensitivities (δaφu ≤ 125 GM) at 740 and 800 nm. To efficiently synthesize these complex photoremovable protecting groups (PPGs), we used step-economic domino reactions. Moreover, those new coumarinyl PPGs display unique bathochromic shifts (≤100 nm) of the uncaging subproducts as a result of the formation of a more conjugated fulvene moiety.

Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.