4-Formylphenylboronic acid
4-Formylphenylboronic acid (CAS 87199-17-5), with the linear formula HCOC<sub>6</sub>H<sub>4</sub>B(OH)<sub>2</sub> and a molecular weight of 149.94, is a valuable organic building block. This compound serves as a key reagent in various cross-coupling reactions, including Suzuki-Miyaura arylation, copper-mediated fluoroalkylation, and palladium-catalyzed oxidative couplings. Its utility extends to the synthesis of complex molecules and functional materials.
- IUPAC
- 4-(Dihydroxyboryl)benzaldehyde,4-Formylbenzeneboronic acid,4-Boronobenzaldehyde,p-Formylbenzeneboronic acid,p-Formylphenylboronic acid
- Synonyms
- 4-(Dihydroxyboryl)benzaldehyde4-Formylbenzeneboronic acid4-Boronobenzaldehydep-Formylbenzeneboronic acidp-Formylphenylboronic acid
Suzuki-Miyaura Cross-Coupling Reactions
This boronic acid is utilized as a coupling partner in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds. These reactions are fundamental in organic synthesis for constructing biaryl compounds and complex molecular architectures.
Fluoroalkylation of Aryl Compounds
It serves as a substrate in copper-mediated ligandless aerobic fluoroalkylation reactions. This process allows for the efficient introduction of fluoroalkyl groups onto aromatic systems, which is important in medicinal chemistry and materials science.
Synthesis of Organic Sensitizers
4-Formylphenylboronic acid has been employed in the preparation of sensitizers, specifically those incorporating a dithiafulvenyl unit as an electron donor, for use in high-efficiency dye-sensitized solar cells.
Preparation of Novel Carbonyl Compounds
The compound acts as a building block in the synthesis of various substituted benzaldehydes and related carbonyl compounds through diverse catalytic transformations.
| Molecular weight | 149.94 |
|---|---|
| Linear formula | HCOC6H4B(OH)2 |
| Assay | ≥95.0% |
| Application | Reagent used for• Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water1 • Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides2 • Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids3 • Triethylamine-catalyzed three-component Hantzsch condensations4 • Copper-catalyzed nitrations5 • Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta6 • Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides7 • Palladium-catalyzed aerobic oxidative cross-coupling reactions8 Reagent used in Preparation of• Sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells9R |
| Melting point | 237-242 °C(lit.) |
Hazard statements
- H314Causes severe skin burns and eye damage
- H317May cause an allergic skin reaction
Precautionary statements
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
- P310Immediately call a POISON CENTER or doctor
| Protective equipment | Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges |
|---|---|
| Transport (UN / ADR) | UN 1759 8 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | C |
| Risk statements (R) | 34 |
| Safety statements (S) | 22-26-36/37/39-45 |
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 4-Formylphenylboronic acid used for?
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4-Formylphenylboronic acid is a reagent used in palladium-catalyzed Suzuki-Miyaura cross-coupling, copper-mediated fluoroalkylation, and in the preparation of organic sensitizers for solar cells, among other synthetic applications.
What is the CAS number and formula for 4-Formylphenylboronic acid?
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The CAS number is 87199-17-5 and the linear formula is HCOC<sub>6</sub>H<sub>4</sub>B(OH)<sub>2</sub>.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies 4-Formylphenylboronic acid with an assay of ≥95.0%. This product is intended for research and laboratory use. TSS does not represent this product as USP, BP, EP, or other pharmacopoeial grades.
What are the safety considerations for handling 4-Formylphenylboronic acid?
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This compound is classified as Danger, with hazards including H314 (Causes severe skin burns and eye damage) and H317 (May cause an allergic skin reaction). Appropriate personal protective equipment, including eyeshields, face shields, gloves, and suitable respiratory protection, must be used. Handle in a well-ventilated area and follow strict laboratory safety protocols.
How is 4-Formylphenylboronic acid packed and shipped?
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4-Formylphenylboronic acid is shipped according to its UN classification UN 1759, Hazard Class 8, Packing Group III. Standard packaging suitable for corrosive solids is used for domestic and international export.
How can I request a sample or quote for 4-Formylphenylboronic acid?
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To request a sample or a quotation for 4-Formylphenylboronic acid, please contact our sales department via the website or direct email, providing your specific requirements and shipping details.
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