6336-44-3

Basic information

• Product Name: [(Z)-prop-1-enyl]boronic acid
• CAS NO: 6336-44-3
• Molecular Formula: C₃H₇BO₂
• Molecular Weight: 85.8984
• Mol File: 6336-44-3.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 175.6°Cat760mmHg
• Flash Point: 60°C
• Density: 0.969g/cm³
• CAS DataBase Reference: [(Z)-prop-1-enyl]boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(Z)-prop-1-enyl]boronic acid(6336-44-3)
• EPA Substance Registry System: [(Z)-prop-1-enyl]boronic acid(6336-44-3)

Safety Data

• Hazardous Substances Data: 6336-44-3(Hazardous Substances Data)

Usage

Description

[(Z)-prop-1-enyl]boronic acid, also known as (Z)-3-butenylboronic acid, is an organoborane compound with the chemical formula C4H9BO2. It is a boronic acid derivative containing a vinyl group and exists as a colorless solid at room temperature. [(Z)-prop-1-enyl]boronic acid is widely used in organic synthesis as a reagent for the preparation of various organic compounds, particularly in the Suzuki-Miyaura coupling reaction. It plays a crucial role in the formation of carbon-carbon bonds, making it a valuable tool in the development of pharmaceuticals, agrochemicals, and materials science. Its versatile chemical properties and utility in synthetic processes make [(Z)-prop-1-enyl]boronic acid a valuable and widely used reagent in the field of organic chemistry.

Uses

Used in Pharmaceutical Industry:
[(Z)-prop-1-enyl]boronic acid is used as a synthetic reagent for the development of various pharmaceutical compounds. Its ability to form carbon-carbon bonds through the Suzuki-Miyaura coupling reaction makes it a key component in the synthesis of complex molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, [(Z)-prop-1-enyl]boronic acid is used as a synthetic reagent for the preparation of agrochemical compounds. Its role in forming carbon-carbon bonds is essential for creating molecules with specific biological activities, such as pesticides and herbicides.
Used in Materials Science:
[(Z)-prop-1-enyl]boronic acid is utilized as a synthetic reagent in materials science for the development of novel materials with unique properties. Its ability to form carbon-carbon bonds contributes to the creation of advanced materials with potential applications in various fields, such as electronics, energy storage, and nanotechnology.
Overall, [(Z)-prop-1-enyl]boronic acid is a versatile and essential reagent in the fields of pharmaceuticals, agrochemicals, and materials science, playing a crucial role in the synthesis of a wide range of compounds with diverse applications.

Upstream product

• 121-43-7 Trimethyl borate 
• 13154-14-8 1-propenylmagnesium bromide 
• 14560-05-5 (1-propenyl)dichlorobrane 
• 1104637-46-8 C₈H₁₂BNO₄ 
• 74-99-7 prop-1-yne 
• 55671-55-1 dibromoborane dimethylsulfide 
• 1310-73-2 sodium hydroxide 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 590-13-6 (Z)-1-propenyl bromide 
• 5419-55-6 Triisopropyl borate 
• 6524-17-0 (Z)-1-propenyllithium 
• 59278-44-3 tris(ethylenedioxyboryl)methane 
• 75-07-0 acetaldehyde 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 22885-64-9 trans-1-(Ethylendioxyboryl)propen 
• 89358-10-1 3-methyl-1-phenylhex-5-ene-1,3-diol 
• 41744-26-7 eupomatenoid 6 
• 873845-89-7 (E)-2-chloro-N,N-diethyl-4-(prop-1-enyl)benzamide 
• 83947-59-5 (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane 
• 847476-29-3 C₂₀H₂₂O₅ 
• 847476-52-2 C₂₀H₂₂O₅ 
• 1426163-34-9 C₁₉H₂₂O₃ 
• 1426163-36-1 C₂₀H₂₄O₄ 
• 911482-75-2 allylboronic acid 2,2-dimethyl-1,3-propanediol ester 
• 72824-04-5 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane 
• 1104637-46-8 C₈H₁₂BNO₄ 

Relevant articles and documents

A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates

Ligand-controlled reactivity plays an important role in transition-metal catalysis, enabling a vast number of efficient transformations to be discovered and developed. However, a single ligand is generally used to promote all steps of the catalytic cycle (e.g., oxidative addition, reductive elimination), a requirement that makes ligand design challenging and limits its generality, especially in relay asymmetric transformations. We hypothesized that multiple ligands with a metal center might be used to sequentially promote multiple catalytic steps, thereby combining complementary catalytic reactivities through a simple combination of simple ligands. With this relay catalysis strategy (L/L?), we report here the first highly regio- and enantioselective remote hydroarylation process. By synergistic combination of a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioenriched α-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp3)-H arylation process.

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

Synthesis of enantiopure cyclic amino acid derivatives via a sequential diastereoselective Petasis reaction/ring closing olefin metathesis process

A novel approach to the synthesis of enantiopure cyclic amino esters is reported. The utilization of allylboronic acid together with (S)-α-methylbenzylamine as a chiral auxiliary in the Petasis/Mannich reaction led to the formation of allylglycine derivatives in good yield and with high diastereoselectivity. Subsequent esterification, N-allylation followed by ring-closing metathesis (RCM) reaction enabled the preparation of enantiomerically pure cyclic α-amino acid derivatives.