36329-85-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylpropylboronic Acid is used as a synthetic intermediate for the production of (hetero)aryl-p-quinone derivatives. These derivatives are known for their potential therapeutic applications in treating mitochondrial diseases, which are a group of disorders caused by failures in the mitochondria, the part of the cell responsible for energy production.
In the synthesis of (hetero)aryl-p-quinone derivatives, 3-Phenylpropylboronic Acid serves as a key building block, providing the necessary structural elements for the formation of the target molecules. The resulting compounds have shown promise in addressing mitochondrial dysfunction and related health issues, making 3-Phenylpropylboronic Acid an important component in the development of novel treatments for mitochondrial diseases.
Additionally, 3-Phenylpropylboronic Acid may also find applications in other industries, such as materials science, where its reactivity and structural properties can be utilized for the development of new materials with specific properties. However, the primary use of 3-PHENYLPROPYLBORONIC ACID is in the pharmaceutical industry, where it plays a crucial role in the synthesis of therapeutic agents for mitochondrial diseases.

Upstream product

• 1462-75-5 3-phenylpropylmagnesium bromide 
• 180286-96-8 (C₆H₅(CH₂)3BO)3 
• 7732-18-5 water 
• 121-43-7 Trimethyl borate 
• 4119-41-9 1-iodo-3-phenylpropan 
• 637-59-2 1-Bromo-3-phenylpropane 
• 329685-40-7 4,4,5,5-tetramethyl-2-(3-phenylpropyl)-[1,3,2]dioxaborolane 
• 300-57-2 allylbenzene 
• 14044-65-6 borane-THF 

Downstream Products

• 501-52-0 3-Phenylpropionic acid 
• 113138-08-2 1-(4-(3-phenylpropyl)phenyl)ethan-1-one 
• 476334-35-7 (1S,2S,6R,8S)-2,9,9-Trimethyl-4-(3-phenyl-propyl)-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 476334-36-8 (1S,2S,6R,8S)-4-((S)-1-Chloro-4-phenyl-butyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 180286-96-8 (C₆H₅(CH₂)3BO)3 
• 143969-42-0 C₆H₄O₂B(CH₂)3C₆H₅ 
• 132350-29-9 2-(3-phenylpropyl)-1,3,2-dioxaborinane 
• 104315-86-8 1-trifluoromethyl-3-phenylpropane 
• 122-97-4 3-Phenyl-1-propanol 
• 178100-79-3 (5,5-difluoropent-4-en-1-yl)benzene 

Relevant academic research and scientific papers

A General C(sp3)-C(sp3) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids

A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp3-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.

Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes

The synthesis of alkyl gem-difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.

Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide

A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.

Palladium-catalyzed borylation of primary alkyl bromides

A mild Pd-catalyzed process for the borylation of alkyl bromides has been developed using bis(pinacolato)diboron as a boron source. This process accommodates the use of a wide range of functional groups on the alkyl bromide substrate. Primary bromides react with complete selectivity in the presence of a secondary bromide. The generality of this approach is demonstrated by its extension to the use of alkyl iodides and alkyl tosylates, as well as borylation reactions employing bis(neopentyl glycolato)diboron as the boron source.

Copper-promoted trifluoromethylation of primary and secondary alkylboronic acids

New couple: The Cu-promoted trifluoromethylation of primary and secondary alkylboronic acids with TMSCF3 extends the scope of transition-metal-catalyzed trifluoromethylation reactions to sp 3-hybridized carbon centers. It also repres

Iron trichloride promoted hydrolysis of potassium organotrifluoroborates

In the presence of iron trichloride, the hydrolysis of potassium organotrifluoroborates occurs smoothly at room temperature to afford the corresponding organoboronic acids in good to excellent yields. The hydrolysis is effective for aryltrifluoroborates as well as alkenyl- and alkyl- trifluoroborates.

P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin.

Synthesis of η-arene derivatives of chromium and molybdenum containing Lewis-acid boron substituents

The compounds Ph(CH2)3B(OH)2 I, [Ph(CH2)3BO]3 II, Ph(CH2)3B(1,2-O2C6H4) III, Ph(CH2)3BC8H14 IV (BC8H14 = 9-borabicyclo[3.3.1]nonan-9-yl), [Cr{η-Ph(CH2)3B(1,2-O2C6H 4)}(CO)3] 1, [Cr{η-Ph(CH2)3BC8H14}(CO) 3] 2, [Cr{η-Ph(CH2)3BBr2·SMe 2}(CO)3] 3, [Cr{η-Ph(CH2)4BC8H14}(CO) 3] 4, [Cr(η-Ph(CH2)4BC8H14}(CO) 2(PPh3)] 5, [Cr{η-PhCH2CH=CH2}(CO)3] 6, [Cr{η-Ph(CH2)2CH=CH2}(CO)3] 7, [Cr{η-Ph(CH2)2η-CH=CH2}(CO) 2] 8, [Cr{η-Ph(CH2)2CH=CH2}(CO) 2(PPh3)] 9, [Li(Et2O)n][Cr{η-PhCH2CH=CH 2}(CO)2{C(O)Ph}] 10, [Li(Et2O)n][Cr{η-Ph(CH2) 2CH=CH2}(CO)2{C(O)Ph}] 11, [Mo{η-Ph(CH2)3BC8H14} 2] 12 and [Cr{η-Ph(CH2)3BOC8H14}(CO) 3] 13, have been prepared and characterised. Compounds 1-5, 12 and 13 have π-donor η-arene ligands which also bear a Lewis-acid α-acceptor boron group. There was no evidence that these boron groups formed ground-state intra- or inter-molecular interactions with the Lewis base functions of the carbonyl oxygen atoms.