219488-99-0

Basic information

• Product Name: 3-Methyl-2-buten-2-ylboronic acid pinacol ester
• Synonyms: 3-Methyl-2-buten-2-ylboronic acid pinacol ester;3-Methyl-2-buten-2-ylboronic acid pinacol ester 95%;2-(1,2-dimethyl-1-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1,2-DIMETHYL-1-PROPEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(WXC07807)
• CAS NO: 219488-99-0
• Molecular Formula: C11H21BO2
• Molecular Weight: 196.09424
• Product Categories: Alkenyl;Boronate Esters;Boronic Acids and Derivatives
• Mol File: 219488-99-0.mol

Chemical Properties

• Flash Point: 71℃
• Appearance: /
• Density: 0.888 g/mL at 25 °C
• Refractive Index: n20/D 1.450
• CAS DataBase Reference: 3-Methyl-2-buten-2-ylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-buten-2-ylboronic acid pinacol ester(219488-99-0)
• EPA Substance Registry System: 3-Methyl-2-buten-2-ylboronic acid pinacol ester(219488-99-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 219488-99-0(Hazardous Substances Data)

Upstream product

• 598-25-4 Dimethylallene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 3017-70-7 2-bromo-3-methylbut-2-ene 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes

Vinyl boronates react with electron-deficient alkyl iodides in the presence of visible light to give boronic esters in which two new C-C bonds have been created. The reaction occurs by radical addition of an electron-deficient alkyl radical to the vinyl boronate followed by electron transfer with another molecule of alkyl iodide, continuing the chain, and triggering a 1,2-metalate rearrangement. In a number of cases, the use of a photoredox catalyst enhances yields significantly. The scope of the radical precursor includes α-iodo ketones, esters, nitriles, primary amides, α-fluorinated halo-acetates and perfluoroalkyl iodides.

An organic boron compound

PROBLEM TO BE SOLVED: To provide a production method of an arylboronic acid ester with a wide range of application substrate, using no heavy metal.SOLUTION: An organic halogen compound represented by the general formula R-X (where, X is Br or I; R is a C1 to 20 alkyl group, a C6 to 14 aryl group, a heterocyclic group comprising 1 to 3 hetero atoms selected from N, O and S, or the like) and a compound represented by the general formula (VI) are reacted in the presence of sodium alkoxide or potassium alkoxide for substitution of a substituted Si moiety and the R moiety to obtain arylboronic acid ester. (In the formula, three Rare each independently a C1 to 6 alkyl group or a C6 to 10 aryl group; and four Reach independently a C1 to 3 alkyl group.)

Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies

A transition-metal-free method has been developed for the boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The base-mediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional group compatibility and high tolerance to steric hindrance. In this study, the scope of this transformation has been extended significantly to include a wide variety of functionalized aryl-, heteroaryl- and alkenyl halides. In particular, the boryl substitution of (E)- and (Z)-alkenyl halides proceeded smoothly to afford the corresponding alkenyl boronates in good to high yields with retention of the configuration using modified reaction conditions. The results of the mechanistic studies suggest that this boryl substitution proceeds via a carbanion-mediated mechanism.

Anomalous reactivity of silylborane: Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems

An unexpected borylation of organic halides with a silyborane in the presence of an alkoxy base has been observed. This formal nucleophilic boryl substitution can be applied to a broad range of substrates with high functional group compatibility. Even sterically hindered aryl bromides afforded the corresponding boryl compounds in high yields. Preliminary mechanistic studies indicated that this boryl substitution is promoted by neither transition-metal contamination nor a radical-mediated process.

Hydroboronation process

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.

Alkene borates and a process for covalently coupling organic compounds

This invention describes a process for covalently coupling organic compounds which comprises reacting an olefinic compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal

A regio- and stereoselective platinum(0)-catalyzed hydroboration of allenes controlled by phosphine ligands

The hydroboration of terminal allenes with pinacolborane was carried out at 50 °C in the presence of a Pt(dba)2/2PR3 catalyst. The formation of one of three possible monohydroboration products was regioselectively synthesized by choo