280559-30-0

Basic information

• Product Name: 2-Phenyl-1-propylboronic acid pinacol ester, 97%
• Synonyms: 2-Phenyl-1-propylboronic acid pinacol ester, 97%
• CAS NO: 280559-30-0
• Molecular Formula: C₁₅H₂₃BO₂
• Molecular Weight: 246.15
• Mol File: 280559-30-0.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 298.4±19.0 °C(Predicted)
• Appearance: /
• Density: 0.96±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Phenyl-1-propylboronic acid pinacol ester, 97%(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-1-propylboronic acid pinacol ester, 97%(280559-30-0)
• EPA Substance Registry System: 2-Phenyl-1-propylboronic acid pinacol ester, 97%(280559-30-0)

Safety Data

• Hazardous Substances Data: 280559-30-0(Hazardous Substances Data)

Usage

Description

2-Phenyl-1-propylboronic acid pinacol ester, 97% is a high-purity chemical compound that serves as a versatile reagent in organic synthesis. It is renowned for its reactivity with diverse functional groups, facilitating the formation of carbon-carbon and carbon-heteroatom bonds. The pinacol ester group in its structure imparts stability and protection to the boronic acid moiety, enabling selective reactions and ease of handling. 2-Phenyl-1-propylboronic acid pinacol ester, 97% is extensively utilized in the synthesis of biologically active molecules across pharmaceutical and agrochemical sectors.

Uses

Used in Organic Synthesis:
2-Phenyl-1-propylboronic acid pinacol ester, 97% is used as a reagent for the preparation of various boronic acid derivatives. Its ability to react with a wide range of functional groups makes it a valuable tool in organic synthesis for creating complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Phenyl-1-propylboronic acid pinacol ester, 97% is used as an intermediate for the synthesis of biologically active compounds. Its versatility in forming carbon-carbon and carbon-heteroatom bonds aids in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-Phenyl-1-propylboronic acid pinacol ester, 97% is also utilized in the agrochemical industry for the synthesis of bioactive compounds with pesticidal or herbicidal properties. Its reactivity and stability contribute to the creation of effective agrochemicals for crop protection and management.

Upstream product

• 98-83-9 isopropenylbenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1141927-87-8 C₉H₁₁BBr₂ 
• 588-73-8 (Z)-β-bromostyrene 
• 73183-34-3 bis(pinacol)diborane 
• 98-82-8 Isopropylbenzene 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 536-74-3 phenylacetylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 100-42-5 styrene 
• 80-48-8 methyl p-toluene sulfonate 
• 873-49-4 cyclopropylbenzene 
• 182810-44-2 4,4,5,5-tetramethyl-2-(2-phenylallyl)-1,3,2-dioxaborolane 
• 680192-98-7 deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 37778-99-7 (S)-2-phenyl-1-propanol 
• 1123-85-9 (+)-(R)-2-phenylpropanol 
• 1392215-07-4 ethyl 2-methylene-5-phenylhexanoate 
• 1123-85-9 (RS)-2-phenyl-1-propanol 

Relevant articles and documents

Dramatic effect of Lewis acids on the rhodium-catalyzed hydroboration of olefins

The addition of Lewis acids such as trispentafluoroboron as cocatalysts has been found to have a dramatic effect on the Rh-catalyzed hydroboration of olefins with pinacol borane. For example, aliphatic olefins do not react at all in noncoordinating solvents, but with the addition of 2% of B(C6F5)3, the reaction is complete in minutes. Similarly, the reaction of aromatic olefins with HBPin occurs slowly and nonselectively in the absence of B(C 6F5)3, but is accelerated and occurs more selectively in its presence. Preliminary mechanistic studies suggest that the B(C6F5)3 needs to be present throughout the course of the reaction, not just at the initiation stage, and implicate this species, along with THF, in the heterolytic cleavage of the B-H bond of HBPin.

Iron-Catalyzed Regioselective Alkenylboration of Olefins

The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.