4-Nitrophenylboronic acid
4-Nitrophenylboronic acid (CAS 24067-17-2), with the molecular formula (O2N)C6H4(B(OH)2) and a molecular weight of 166.93 g/mol, is a vital organometallic reagent. It is primarily utilised in various cross-coupling reactions, including Suzuki-Miyaura couplings and direct arylation of benzylic carbons. This compound serves as a key building block in organic synthesis for creating complex molecules.
- IUPAC
- 4-Nitrobenzeneboronic acid,p-Nitrophenylboronic acid,p-nitro-benzeneboronic acid
- Synonyms
- 4-Nitrobenzeneboronic acidp-Nitrophenylboronic acidp-nitro-benzeneboronic acid
Suzuki-Miyaura Cross-Couplings
4-Nitrophenylboronic acid is employed as a substrate in ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. It is also used in regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations.
Direct Arylation Reactions
This boronic acid is a reagent in Ruthenium-catalyzed direct arylation of benzylic sp3 carbons of acyclic amines. It also participates in C-H activation reactions.
N-Arylation and Cyanation
It is utilized in the N-arylation of phenylurea using a copper acetylacetonate catalyst and in copper-mediated cyanations.
Synthesis of Heterocycles
The compound finds application in tandem palladium-catalyzed intramolecular aminocarbonylation and annulations, contributing to the synthesis of heterocyclic structures.
| Molecular weight | 166.93 |
|---|---|
| Linear formula | (O2N)C6H4(B(OH)2) |
| Assay | ≥95.0% |
| Application | Reagent used for• Ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings1 • Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines2 • Diels-Alder or C-H activation reactions3 • Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations4• N-arylation of phenylurea using copper acetylacetonate catalyst5 • Environmentally benign one-pot synthesis through a double arylation process6 • Copper-mediated cyanations7 • copper-catalyzed arylations8 • Regioselective glycosylations9 • Suzuki couplings followed by arylations10 • X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addit |
| Melting point | 285-290 °C (dec.) |
Hazard statements
- H302Harmful if swallowed
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22 |
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-Nitrophenylboronic acid used for?
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4-Nitrophenylboronic acid is used as a reagent in various organic synthesis applications, notably in palladium-catalyzed Suzuki-Miyaura cross-couplings, Ruthenium-catalyzed direct arylation of benzylic carbons, C-H activation reactions, and copper-mediated cyanations.
What are the CAS number and molecular formula for 4-Nitrophenylboronic acid?
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The CAS number for 4-Nitrophenylboronic acid is 24067-17-2, and its linear formula is (O2N)C6H4(B(OH)2).
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies 4-Nitrophenylboronic acid with a minimum purity of 95.0%. This product is intended for research and laboratory use. Tech Serve Solutions does not represent it as USP, BP, or EP grade.
What are the safety considerations when handling 4-Nitrophenylboronic acid?
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4-Nitrophenylboronic acid is classified with GHS07 symbol and a 'Warning' signal word. It carries the hazard statement H302 (Harmful if swallowed). Appropriate personal protective equipment, including a dust mask (type N95 or equivalent), eyeshields, and gloves, should be worn during handling.
How is 4-Nitrophenylboronic acid packed, shipped, and exported?
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Tech Serve Solutions offers 4-Nitrophenylboronic acid in various pack sizes suitable for laboratory and research needs. We are experienced in exporting chemicals globally, adhering to all necessary regulations for safe and compliant international shipment.
How can I request a quote or sample of 4-Nitrophenylboronic acid?
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To request a quote or a sample of 4-Nitrophenylboronic acid, please visit our website or contact our sales department directly. Our team will be pleased to assist you with your requirements.
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