157945-83-0

Basic information

• Product Name: (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(E)-2-(3,3-dimethylbut-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(1E)-3,3-Dimethyl-1-butenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 157945-83-0
• Molecular Formula: C₁₂H₂₃BO₂
• Molecular Weight: 210.12082
• Mol File: 157945-83-0.mol
• Article Data: 35

Chemical Properties

• Melting Point: 35 °C
• Boiling Point: 75 °C(Press: 2.0 Torr)
• Appearance: /
• Density: 0.88±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(157945-83-0)
• EPA Substance Registry System: (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(157945-83-0)

Safety Data

• Hazardous Substances Data: 157945-83-0(Hazardous Substances Data)

Usage

General Description

(E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound that consists of a boron atom bonded to four methyl groups and a molecule of 1,3,2-dioxaborolane, with an additional (E)-2-(3,3-dimethylbut-1-en-1-yl) substituent. It is commonly used as a reagent in organic chemistry, particularly in the synthesis of complex organic molecules. (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is also a versatile building block for the preparation of various boron-containing compounds, which have widespread applications in materials science, pharmaceuticals, and agrochemicals. Additionally, it exhibits unique chemical properties, making it a valuable tool for the development of new chemical reactions and methodologies in synthetic chemistry.

Upstream product

• 33693-77-5 2-Bromo-3,3-dimethyl-1-butene 
• 73183-34-3 bis(pinacol)diborane 
• 64245-24-5 (Z)-3,3-dimethyl-1-iodo-1-butene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 7732-18-5 water 
• 558-17-8 tert-Butyl iodide 
• 347389-74-6 2-ethynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 680192-98-7 deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 630-19-3 pivalaldehyde 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 558-37-2 tert-butylethylene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 83622-41-7 pinacol dichloromethylboronic ester 

Downstream Products

• 86595-37-1 trans-2-tert-butylvinylboronic acid 
• 1453804-90-4 C₁₉H₂₁NO 
• 1453804-99-3 C₂₁H₂₅NO 
• 1453804-76-6 C₁₉H₂₁NO 
• 193755-69-0 hexakis-[(E)-(3,3-dimethyl-1-butenyl)]benzene 
• 749885-70-9 2-(trans-2-tert-butylcyclopropyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Relevant articles and documents

Hexamethyldisilazane Lithium (LiHMDS)-Promoted Hydroboration of Alkynes and Alkenes with Pinacolborane

Lithium-promoted hydroboration of alkynes and alkenes using commercially available hexamethyldisilazane lithium as a precatalyst and HBpin as a hydride source has been developed. This method will be appealing for organic synthesis because of its remarkable substrate tolerance and good yields. Mechanistic studies revealed that the hydroboration proceeds through the in situ-formed BH3species, which acts to drive the turnover of the hydroboration of alkynes and alkenes.

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. (Figure presented.).

Creating High Regioselectivity by Electronic Metal-Support Interaction of a Single-Atomic-Site Catalyst

Ligands are the most commonly used means to control the regioselectivity of organic reactions. It is very important to develop new regioselective control methods for organic synthesis. In this study, we designed and synthesized a single-atomic-site catalyst (SAC), namely, Cu1-TiC, with strong electronic metal-support interaction (EMSI) effects by studying various reaction mechanisms. π cloud back-donation to the alkyne on the metal catalytic intermediate was enhanced during the reaction by using transient electron-rich characteristics. In this way, the reaction achieved highly linear-E-type regioselective conversion of electronically unbiased alkynes and completely avoided the formation of branched isomers (ln:br >100:1, TON up to 612, 3 times higher than previously recorded). The structural elements of the SACs were designed following the requirements of the synthesis mechanism. Every element in the catalyst played an important role in the synthesis mechanism. This demonstrated that the EMSI, which is normally thought to be responsible for the improvement in catalytic efficiency and durability in heterogeneous catalysis, now first shows exciting potential for regulating the regioselectivity in homogeneous catalysis.