trans-2-Phenylvinylboronic acid
trans-2-Phenylvinylboronic acid (CAS: 6783-05-7), with the molecular formula C6H5CH=CHB(OH)2, is an organoboronic acid primarily utilised as a versatile reagent. It is widely employed in palladium-catalyzed Suzuki-Miyaura coupling reactions and various other organometallic transformations, facilitating the synthesis of complex organic molecules and intermediates. Its utility extends to diastereoselective synthesis and the preparation of valuable amino acid derivatives.
- IUPAC
- (E)-2-phenyl-Etheneboronic acid,(E)-Phenylethenylboronic acid,(E)-Styreneboronic acid,(E)-Styrylboronic acid,trans-(2-Phenylethenyl)boronic acid,trans-Phenylvinyl boronic acid
- Synonyms
- (E)-2-phenyl-Etheneboronic acid(E)-Phenylethenylboronic acid(E)-Styreneboronic acid(E)-Styrylboronic acidtrans-(2-Phenylethenyl)boronic acidtrans-Phenylvinyl boronic acid
Suzuki-Miyaura Coupling Reagent
This boronic acid is a key substrate in palladium-catalyzed Suzuki-Miyaura coupling reactions, enabling the formation of carbon-carbon bonds with aryl and vinyl halides.
Organometallic Synthesis
It participates in a range of organometallic reactions, including rhodium-catalyzed amination of aryl azides and copper-mediated cyanation, offering diverse synthetic pathways.
Diastereoselective Synthesis
The compound is instrumental in achieving diastereoselective synthesis through processes such as Pd-catalyzed Heck-Suzuki cascade reactions and iridium-catalyzed additions.
Preparation of Amino Acids and Derivatives
It serves as a reagent in the Petasis borono-Mannich reaction for the preparation of optically active unsaturated amino acids and in the Petasis 3-component reaction for amino alcohol dienes.
| Molecular weight | 147.97 |
|---|---|
| Linear formula | C6H5CH=CHB(OH)2 |
| Assay | 97% |
| Application | Reagent used for• Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions1 • Rhodium (Rh)-catalyzed intramolecular amination of aryl azides2 • Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction3 • Copper (Cu)-mediated cyanation4 • Rhodium (Rh)-catalyzed asymmetric addition5 • Diastereoselective synthesis via iridium (Ir)-catalyzed addition6 • Palladium (Pd)-catalyzed cascade cyclization7 Reagent used in Preparation of • Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction8 • Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization9 |
| Melting point | 146-156 °C(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is trans-2-Phenylvinylboronic acid used for?
+
trans-2-Phenylvinylboronic acid is primarily used as a reagent in palladium-catalyzed Suzuki-Miyaura coupling reactions, rhodium-catalyzed intramolecular amination of aryl azides, and various other organometallic transformations for diastereoselective synthesis and preparation of amino acid derivatives.
What is the CAS number and chemical formula for trans-2-Phenylvinylboronic acid?
+
The CAS number is 6783-05-7 and the linear chemical formula is C6H5CH=CHB(OH)2.
What grade and purity does Tech Serve Solutions supply for trans-2-Phenylvinylboronic acid?
+
Tech Serve Solutions supplies trans-2-Phenylvinylboronic acid with an assay of 97%. This product is intended for research and chemical synthesis purposes; it is not supplied as USP, BP, EP, or pharmacopoeia grade.
What are the safety and handling considerations for trans-2-Phenylvinylboronic acid?
+
Handling trans-2-Phenylvinylboronic acid requires appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter should be used. The substance has a WGK Germany rating of 3, indicating it is hazardous to water.
How is trans-2-Phenylvinylboronic acid packed and exported?
+
Tech Serve Solutions ensures secure packaging suitable for international export of chemicals like trans-2-Phenylvinylboronic acid, adhering to all relevant shipping regulations.
How can I request a sample or quote for trans-2-Phenylvinylboronic acid?
+
To request a sample or a quotation for trans-2-Phenylvinylboronic acid, please contact our sales department through the website or by phone.
▶ Related products
1-(2-Fluorobenzyl)piperazine
C11H15FN2
Chemical Synthesis
1-(2-Fluorophenyl)biguanide hydrochloride
Chemical Synthesis
1-(2-Fluorophenyl)cyclopropanecarboxylic acid
C10H9FO2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine
C10H13FN2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine monohydrochloride
C10H13FN2 · HCl
Chemical Synthesis
1-(2-Furoyl)-1H-benzotriazole
C11H7N3O2
Chemical Synthesis
1-(2-Furoyl)piperazine
C9H12N2O2
Chemical Synthesis
1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione
Chemical Synthesis
▶ Explore more
3-Methyl-1,5-di-p-tolyl-1,4-pentazadiene
Chemical Synthesis
3-Methyl-1,5-pentanediol
Chemical Synthesis
3-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine
C11H13N3
Chemical Synthesis
3-Methyl-1-(3′-sulfoamidophenyl)-5-pyrazolone
C10H11N3O3S
Chemical Synthesis