7547-97-9

Basic information

• Product Name: TRANS-1-PROPEN-1-YLBORONIC ACID
• Synonyms: TRANS-1-PROPEN-1-YLBORONIC ACID;[(1E)-prop-1-en-1-yl]boronic acid;Prop-1-en-1-ylboronic acid;(E)-prop-1-en-1-ylboronic acid;trans-1-Propen-1-ylboronic acid >=95.0%;(E)-1-propen-1-yl-boronicacid;(E)-Prop-1-enylboronic acid;trans-1-Propeneboronic acid
• CAS NO: 7547-97-9
• Molecular Formula: C₃H₇BO₂
• Molecular Weight: 85.89748
• EINECS: 200-258-5
• Product Categories: blocks;BoronicAcids;Alkenyl;Boronic Acids;Boronic Acids and Derivatives;Boric Acid| Boric Acid Ester| Potassium Trifluoroborate
• Mol File: 7547-97-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 123-127 °C(lit.)
• Boiling Point: 175.6°C at 760 mmHg
• Flash Point: 60°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 0.351mmHg at 25°C
• Refractive Index: 1.421
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Very Slightly, Heated), Methanol (Very Slightly)
• PKA: 9.80±0.43(Predicted)
• CAS DataBase Reference: TRANS-1-PROPEN-1-YLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1-PROPEN-1-YLBORONIC ACID(7547-97-9)
• EPA Substance Registry System: TRANS-1-PROPEN-1-YLBORONIC ACID(7547-97-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7547-97-9(Hazardous Substances Data)

Usage

Description

TRANS-1-PROPEN-1-YLBORONIC ACID is an organic compound that serves as a versatile reagent in various chemical reactions and synthesis processes. It is characterized by its boron-carbon bond and a double bond, which allows it to participate in multiple types of coupling reactions. This unique structure makes it a valuable building block in the synthesis of complex organic molecules and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant for the preparation of alkynylphenoxyacetic acids, which act as DP2 receptor antagonists. These antagonists are crucial for the treatment of allergic inflammatory diseases, providing relief from symptoms and managing the underlying inflammation.
Used in Organic Synthesis:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant in palladium-phosphine-catalyzed Suzuki-Miyaura coupling reactions. This reaction is a powerful tool in organic synthesis, allowing for the formation of carbon-carbon bonds between an organoboron compound and an organohalide, leading to the creation of a wide range of complex organic molecules.
Used in Biochemical Research:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant for the preparation of tetrahydrobenzothiophenes. These compounds serve as conformationally restricted enol-mimic inhibitors of type II dehydroquinase. This makes them valuable in biochemical research, particularly in the study of enzyme mechanisms and the development of potential therapeutic agents.
Used in Organic Chemistry:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant in Cu(II)-mediated Ullmann-type coupling. This reaction is an important method for forming carbon-carbon bonds, particularly in the synthesis of biaryl compounds, which are prevalent in pharmaceuticals, agrochemicals, and materials science.
Used in Advanced Synthesis Techniques:
TRANS-1-PROPEN-1-YLBORONIC ACID is used in the preparation of highly substituted benzannulated cyclooctanol derivatives. This is achieved through samarium diiodide-mediated cyclization, a technique that allows for the formation of complex ring systems with multiple stereocenters, which are often found in biologically active natural products and pharmaceuticals.
Used in Stereoselective Synthesis:
TRANS-1-PROPEN-1-YLBORONIC ACID is used as a reactant in nickel-catalyzed three-component reductive coupling with alkynes and enones. This reaction provides a route to stereospecific dienes, which are important building blocks in the synthesis of natural products and pharmaceuticals, as well as materials with unique properties.

InChI:InChI=1/C3H7BO2/c1-2-3-4(5)6/h2-3,5-6H,1H3/b3-2+

Upstream product

• 74-99-7 prop-1-yne 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5419-55-6 Triisopropyl borate 
• 1730-25-2 allylmagnesium bromide 
• 121-43-7 Trimethyl borate 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 101-36-0 tri-n-butoxyboroxin 
• 51851-79-7 diisopropyl allylboronate 
• 1594-94-1 allyl dimethyl boronic acid ester 
• 55671-55-1 dibromoborane dimethylsulfide 
• 13154-14-8 1-propenylmagnesium bromide 
• 59278-44-3 tris(ethylenedioxyboryl)methane 
• 75-07-0 acetaldehyde 
• 6524-17-0 (Z)-1-propenyllithium 

Downstream Products

• 909726-02-9 benzyl[2-(propen-1-yl)phenyl]amine 
• 909726-03-0 benzyl[4-methoxy-2-(propen-1-yl)phenyl]amine 
• 1000792-39-1 2-[(Z)-1-propenyl]-2-cyclohexen-1-one 
• 65001-42-5 (E)-methyl-(2-propenylphenyl)amine 
• 1016170-27-6 (E)-ethyl-(2-propenylphenyl)amine 
• 1016170-28-7 (E)-benzyl-(4-fluoro-2-propenylphenyl)amine 
• 925441-85-6 2,3,5-Trimethyl-6-[(1E)-1-propenyl]benzaldehyde 
• 1114265-46-1 Z-(2R,4aR,6S,10bS)-4,4a,6,10b-tetrahydro-6-methoxy-2-phenyl-9-(1-propenyl)-1,3-dioxino[4',5':5,6]-pyrano[4,3-d]-pyrimidine 
• 83947-59-5 (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane 
• 1151913-51-7 C₁₀H₁₁NO₂ 
• 1151913-50-6 (E)-methyl 5-(prop-1-en-1-yl)picolinate 

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.