83947-59-5

Basic information

• Product Name: 4,4,5,5-Tetramethyl-2-((Z)-1-propenyl)-1,3,2-dioxaborolane
• Synonyms: 4,4,5,5-Tetramethyl-2-((Z)-1-propenyl)-1,3,2-dioxaborolane;cis-1-Propenylboronic Acid Pinacol Ester;cis-1-Propeneboronic acid pinacol ester;cis-2-(1-Propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-[(Z)-prop-1-enyl]-1,3,2-dioxaborolane
• CAS NO: 83947-59-5
• Molecular Formula: C₉H₁₇BO₂
• Molecular Weight: 168.04108
• Mol File: 83947-59-5.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 157.2±23.0℃ (760 Torr)
• Flash Point: 48.9±22.6℃
• Appearance: /
• Density: 0.89±0.1 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-((Z)-1-propenyl)-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-((Z)-1-propenyl)-1,3,2-dioxaborolane(83947-59-5)
• EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-((Z)-1-propenyl)-1,3,2-dioxaborolane(83947-59-5)

Safety Data

• Statements: 10
• Hazardous Substances Data: 83947-59-5(Hazardous Substances Data)

Usage

Uses

cis-1-Propenylboronic acid pinacol ester is an substituted alkylboronate that is used in the synthetic preparation of various pharmaceutical goods.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 7547-96-8 1-propenylboronic acid 
• 590-13-6 (Z)-1-propenyl bromide 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 74-99-7 prop-1-yne 
• 917-54-4 methyllithium 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13154-14-8 (Z)-1-propenylmagnesium bromide 
• 6336-44-3 cis-1-propenylboronic acid 
• 14559-96-7 dibutyl 1-propene-1-boronate acid 
• 13311-54-1 2,3-dimethyl-2,3-butanediol monohydrate 
• 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 

Downstream Products

• 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 
• 581802-24-6 (E)-2-[2-(2-bromo-phenyl)-vinyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 873-66-5 1-propenylbenzene 
• 98-83-9 isopropenylbenzene 

Relevant articles and documents

(Z)-Selective Hydroboration of Terminal Alkynes Catalyzed by a PSP-Pincer Rhodium Complex

A highly (Z)-selective hydroboration of terminal alkynes was achieved using a thioxanthene-based PSP-pincer rhodium catalyst. This hydroboration exhibited good chemoselectivity toward alkynes over carbonyl compounds such as ketones and aldehydes. The mechanistic studies indicated the involvement of rhodium-vinylidene intermediates, and the high (Z)-selectivity could be attributed to the rigid and electron-rich nature of the PSP-rhodium catalyst.

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.