83947-58-4

Basic information

• Product Name: 4,4,5,5-Tetramethyl-2-((E)-propenyl)[1,3,2]dioxaborolane
• Synonyms: (E)-4,4,5,5-Tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane;(E)-4,4,5,5-Tetramethyl-2-(prop-1-enyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-((E)-1-propenyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-((E)-propenyl)[1,3,2]dioxaborolane;trans-1-Propenylboronic acid pinacol ester;trans-1-Propenylboronic acid pinacol ester 97%;trans-1-Propeneboronic acid pinacol ester;trans-2-(1-Propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 83947-58-4
• Molecular Formula: C₉H₁₇BO₂
• Molecular Weight: 186.05636
• Mol File: 83947-58-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 46-47℃ (4 Torr)
• Flash Point: 48.9±22.6℃
• Appearance: /
• Density: 0.89±0.1 g/cm3 (20 ºC 760 Torr)
• Refractive Index: n20/D1.433
• CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-((E)-propenyl)[1,3,2]dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-((E)-propenyl)[1,3,2]dioxaborolane(83947-58-4)
• EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-((E)-propenyl)[1,3,2]dioxaborolane(83947-58-4)

Safety Data

• Statements: 10
• RIDADR: UN 1993C 3 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 83947-58-4(Hazardous Substances Data)

Upstream product

• 6524-17-0 (Z)-1-propenyllithium 
• 83622-42-8 2-(chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13154-14-8 (Z)-1-propenylmagnesium bromide 
• 6386-72-7 (E)-propenyl lithium 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 6336-44-3 cis-1-propenylboronic acid 
• 75-07-0 acetaldehyde 
• 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 
• 7547-96-8 1-propenylboronic acid 
• 6336-44-3 (E)-propenylboronic acid 
• 14559-96-7 dibutyl 1-propene-1-boronate acid 
• 13311-54-1 2,3-dimethyl-2,3-butanediol monohydrate 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 83947-59-5 (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane 

Downstream Products

• 873-66-5 1-propenylbenzene 
• 98-83-9 isopropenylbenzene 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 74213-48-2 4,4,5,5-tetramethyl-2-[(1Z)-2-phenylethenyl]-1,3,2-dioxaborolane 
• 172512-89-9 (Z)-2-(2-cyclohexyl-vinyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 581802-26-8 (E)-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl-2-ol 
• 83947-55-1 pinacolato (E)-1-octenylboronate 
• 74213-47-1 (Z)-4,4,5,5-tetramethyl-2-(oct-1-en-1-yl)-1,3,2-dioxaborolane 
• 167693-19-8 2-(cyclopentylidenemethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 581802-24-6 (E)-2-[2-(2-bromo-phenyl)-vinyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 884864-15-7 benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester 
• 581802-27-9 benzoic acid (E)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester 
• 74213-49-3 2-(cyclohexylidenemethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

ISOMERIZATION OF ALKENES

The present invention relates to an isomerization method for alkenes, comprising of reaction an alkene with a Ni(I)-compound. By this method, E-Alkenes are obtained in excellent yield.

Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity

A protocol for the preparation of α-boryl-α-bromoketones from alkenyl MIDA boronates was developed and applied to functionalized aliphatic derivatives. The reaction sequence included regioselective hydroxybromination of olefin moiety, followed by oxidation of alcohol group with Dess–Martin periodinane. The target trifunctional boronate-containing derivatives were obtained in up to 94 % yield over two steps starting from alkenyl MIDA boronates. In some cases, functional groups present in the substrate participated in the bromohydroxylation step via intramolecular nucleophilic attack at the bromonium cation leading to cyclic products. Additionally, the reactivity of aliphatic α-boryl-α-bromoketones was illustrated by nucleophilic substitution at the α-C atom and heterocyclization reactions.

E-Olefins through intramolecular radical relocation

Full control over the selectivity of carbon-carbon double-bond migrations would enable access to stereochemically defined olefins that are central to the pharmaceutical, food, fragrance, materials, and petrochemical arenas. The vast majority of double-bond migrations investigated over the past 60 years capitalize on precious-metal hydrides that are frequently associated with reversible equilibria, hydrogen scrambling, incomplete E/Z stereoselection, and/or high cost. Here, we report a fundamentally different, radical-based approach.We showcase a nonprecious, reductant-free, and atom-economical nickel (Ni)(I)-catalyzed intramolecular 1,3-hydrogen atom relocation to yield E-olefins within 3 hours at room temperature. Remote installations of E-olefins over extended distances are also demonstrated.