4-Methoxycarbonylphenylboronic acid
4-Methoxycarbonylphenylboronic acid (CAS 99768-12-4; Formula C8H9BO4; Molar Mass 179.97) is a key aryl boronic acid derivative. It serves as a valuable reagent in various organic synthesis reactions, including palladium-catalyzed cross-couplings and C-H functionalization. Its utility extends to the preparation of complex molecules like chromenones and nanoparticles, making it an important building block in pharmaceutical research and materials science.
- IUPAC
- (4-Carbomethoxyphenyl)boronic acid,4-Carbomethoxybenzeneboronic acid,4-Methoxycarbonylbenzeneboronic acid,4-borono-benzoic acid 1-methyl ester,p-(Methoxycarbonyl)boronic acid,p-(Methoxycarbonyl)phenylboronic acid,p-borono-benzoic acid methyl ester,Methyl 4-boronobenzoate,Methyl p-boronobenzoate
- Synonyms
- Methyl 4-boronobenzoate(4-Carbomethoxyphenyl)boronic acid4-Carbomethoxybenzeneboronic acid4-Methoxycarbonylbenzeneboronic acid4-borono-benzoic acid 1-methyl esterp-(Methoxycarbonyl)boronic acidp-(Methoxycarbonyl)phenylboronic acidp-borono-benzoic acid methyl esterMethyl p-boronobenzoate
Organic Synthesis Reagent
This compound is employed as a reagent in tandem-type Pd(II)-catalyzed oxidative Heck reactions and intramolecular C-H amidation sequences. It also participates in copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides.
Cross-Coupling Reactions
It is used in biaryl synthesis via nickel-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl halides with arylboronic acids. The compound is also involved in cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling.
Nitration Reactions
4-Methoxycarbonylphenylboronic acid is utilized in one-pot ipso-nitration of arylboronic acids and in copper-catalyzed nitration reactions.
Material Science Applications
The reagent contributes to the preparation of Pt nanoparticles@Photoactive metal-organic frameworks, which result in efficient hydrogen evolution via synergistic photoexcitation and electron injection.
Preparation of Chromenones
It is a key intermediate in the preparation of chromenones exhibiting bradykinin B1 antagonistic activity.
| Molecular weight | 179.97 |
|---|---|
| Empirical formula | C8H9BO4 |
| Application | Reagent used for• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence1 • Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides2 • One-pot ipso-nitration of arylboronic acids3 • Copper-catalyzed nitration4 • Cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling5 • Reagent used in Preparation of• Biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6† • Chromenones and their bradykinin B1 antagonistic activit7† • Pt nanoparticles@Photoactive metal-organic frameworks resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injectio8† • |
| Melting point | 197-200 °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 4-Methoxycarbonylphenylboronic acid used for?
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4-Methoxycarbonylphenylboronic acid is used as a reagent in various organic synthesis reactions, including Heck reactions, amidation, fluoroalkylation, nitration, Suzuki-Miyaura cross-coupling, and in the preparation of chromenones and advanced materials like Pt nanoparticles within metal-organic frameworks.
What is the CAS number and formula for 4-Methoxycarbonylphenylboronic acid?
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The CAS number is 99768-12-4, and the empirical formula is C8H9BO4.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies 4-Methoxycarbonylphenylboronic acid as a research-grade chemical. We do not represent it as USP, BP, EP, or any other pharmacopoeia grade.
What are the safety and handling precautions for 4-Methoxycarbonylphenylboronic acid?
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Appropriate personal protective equipment, including eyeshields and gloves, should be worn. A type N95 (US) or type P1 (EN143) respirator filter is recommended. Please consult the Safety Data Sheet (SDS) for comprehensive handling information.
How is 4-Methoxycarbonylphenylboronic acid packed, shipped, and exported?
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Tech Serve Solutions offers professional packing, shipping, and export services for 4-Methoxycarbonylphenylboronic acid globally, adhering to all relevant regulations for chemical transport.
How can I request a sample or quote for 4-Methoxycarbonylphenylboronic acid?
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To request a sample or quote, please use the contact form on our website or contact our sales department directly. Provide the product name and CAS number (99768-12-4) for prompt service.
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