147609-46-9

Basic information

• Product Name: 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 147609-46-9
• Molecular Weight: 244.142
• Mol File: 147609-46-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(147609-46-9)
• EPA Substance Registry System: 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(147609-46-9)

Safety Data

• Hazardous Substances Data: 147609-46-9(Hazardous Substances Data)

Usage

Type of compound

Boron-containing compound

Type of reaction

Suzuki-Miyaura coupling (a method for forming carbon-carbon bonds in complex organic molecules)

Reactivity

Participates in cross-coupling reactions with a variety of organic halides and pseudohalides

Uses

Construction of pharmaceuticals, agrochemicals, and other fine chemicals

Properties

+ Boronic ester

+ Tetramethyl

Four methyl groups attached to a central atom or group of atoms

+ 2E configuration

Indicates the position of the double bond in the compound

+ 3-Phenyl-2-propen-1-yl group

A phenyl group and a propenyl group attached to the same carbon atom

+ Boron atom

A chemical element used in various industrial and chemical applications. In this compound, it is part of the boronic ester group.

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 42599-24-6 E-styryl iodide 
• 129422-12-4 ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)zinc(II) iodide 
• 104-54-1 3-Phenylpropenol 
• 73183-34-3 bis(pinacol)diborane 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 2687-12-9 cinnamyl chloride 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 300-57-2 allylbenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 75927-49-0 pinacol vinylboronate 
• 177573-86-3 (E)-4,4,5,5-tetramethyl-2-(3-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane 

Downstream Products

• 1005-64-7 trans-1-phenyl-1-butene 
• 30953-25-4 2-phenylbut-3-enoic acid 
• 2243-53-0 trans-styrylacetic acid 
• 104046-95-9 (±)-anti-1-(4-cyanophenyl)-2-phenylbut-3-en-1-ol 
• 107182-22-9 (±)-anti-1-(4-chlorophenyl)-2-phenylbut-3-en-1-ol 
• 84363-86-0 (±)-anti-1,4-diphenylhex-5-en-3-ol 
• 84363-88-2 (1RS,2RS)-1-cyclohexyl-2-phenylbut-3-en-1-ol 
• 84363-90-6 (1RS,2SR)-1,2-diphenyl-3-buten-1-ol 

Relevant articles and documents

Nickel-Catalysed Allylboration of Aldehydes

A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.

Direct synthesis of alkenyl boronic esters from unfunctionalized alkenes: A boryl-heck reaction

We report the first example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts.

Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes

The highly selective copper-catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a (Z)-σ-allyl copper species, which was isolated and structurally characterized by single-crystal X-ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3-diene derivatives to afford allylboranes and homoallylboranes. Copyright