4-Iodophenylboronic acid
4-Iodophenylboronic acid (CAS: 5122-99-6, Formula: IC6H4B(OH)2, MW: 247.83) is a versatile organoboronic acid reagent. It is primarily employed in various palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura couplings, and copper-mediated processes. This compound serves as a key building block in organic synthesis, enabling the formation of carbon-carbon and carbon-heteroatom bonds in the preparation of complex molecules and pharmaceutical intermediates.
- IUPAC
- B-(4-iodophenyl)-boronic acid,p-iodo-benzeneboronic acid,p-Iodophenylboronic acid
- Synonyms
- B-(4-iodophenyl)-boronic acidp-iodo-benzeneboronic acidp-Iodophenylboronic acid
Suzuki-Miyaura Cross-Coupling Reactions
4-Iodophenylboronic acid is a valuable substrate in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. These reactions are crucial for forming carbon-carbon bonds, facilitating the synthesis of biaryl compounds and other complex organic structures.
Copper-Mediated Reactions
This boronic acid participates in copper-mediated reactions, such as fluoroalkylation and oxidative hydroxylation. These processes utilise copper catalysts to achieve specific functionalisation of organic molecules.
Organometallic Synthesis
As an aryl boronic acid derivative, it is a key reagent in organometallic chemistry. It serves as a precursor for various transformations and the synthesis of functionalised aromatic compounds.
Preparation of Pharmaceutical Intermediates
The compound is utilised in synthetic routes towards pleuromutilin derivatives and other biologically relevant molecules. Its reactivity allows for the construction of intricate molecular architectures found in pharmaceuticals.
| Molecular weight | 247.83 |
|---|---|
| Linear formula | IC6H4B(OH)2 |
| Assay | ≥95.0% |
| Application | Reagent used for• Copper-mediated ligandless aerobic fluoroalkylation1 • Palladium-catalyzed aerobic oxidative cross-coupling reactions2 • Recyclable magnetic-nanoparticle-supported palladium catalyst for the Suzuki coupling reactions3 • Oxidative hydroxylation using a copper (Cu) catalyst4 • Ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling5 • Homocoupling using gold salts as a catalyst6 • Ruthenium (Ru)-catalyzed cross-coupling7 • CuI-catalyzed Suzuki coupling reactions8 • Palladium-catalyzed domino Heck-Mizoroki/Suzuki-Miyaura reactions9 • Manganese triacetate-mediated radical additions of arylboronic acids to alkenes10 Reagent used in Preparation of • Pleuromutilin derivatives for ribosomal bi |
| Melting point | 326-330 °C(lit.) |
Hazard statements
- H302Harmful if swallowed
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22-36/37/38 |
| Safety statements (S) | 26-36 |
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-Iodophenylboronic acid used for?
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4-Iodophenylboronic acid is a reagent used in various organic synthesis reactions, notably in copper-mediated and palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura couplings. It is also used in the preparation of pharmaceutical intermediates.
What are the CAS number and formula for 4-Iodophenylboronic acid?
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The CAS number is 5122-99-6, and the linear formula is IC6H4B(OH)2.
What grade and purity does Tech Serve Solutions supply for 4-Iodophenylboronic acid?
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Tech Serve Solutions supplies 4-Iodophenylboronic acid with an assay of ≥95.0%. We do not represent this product as USP, BP, EP, or any pharmacopoeia grade.
What are the safety and handling precautions for 4-Iodophenylboronic acid?
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4-Iodophenylboronic acid is classified as a Warning. It is harmful if swallowed (H302) and causes skin (H315), eye (H319), and respiratory irritation (H335). Appropriate personal protective equipment, including a dust mask (type N95), eyeshields, and gloves, should be worn during handling. Ensure adequate ventilation.
How is 4-Iodophenylboronic acid packed and shipped?
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Tech Serve Solutions safely packs and exports 4-Iodophenylboronic acid globally, adhering to all relevant shipping regulations for chemical reagents.
How can I request a quote or sample of 4-Iodophenylboronic acid?
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To request a quote or a sample of 4-Iodophenylboronic acid, please contact our sales team through the TSS website or by direct enquiry.
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