4-(Methylthio)phenylboronic acid
4-(Methylthio)phenylboronic acid (CAS 98546-51-1; CH3SC6H4B(OH)2) is a key organoboron compound with a molecular weight of 168.02. It serves as a versatile building block in organic synthesis, notably participating in various cross-coupling reactions and addition reactions. This compound is essential for the construction of complex organic molecules, finding utility across research and development sectors in pharmaceuticals and materials science.
- IUPAC
- 4-(Methylsulfanyl)benzeneboronic acid,4-(Methylsulfanyl)phenylboronic acid,4-(Methylthio)benzeneboronic acid
- Synonyms
- 4-(Methylsulfanyl)benzeneboronic acid4-(Methylsulfanyl)phenylboronic acid4-(Methylthio)benzeneboronic acid
Suzuki-Miyaura Cross-Coupling Reactions
4-(Methylthio)phenylboronic acid is a valuable reactant in Suzuki-Miyaura cross-coupling reactions. It can be coupled with compounds such as 2-aryl-1-bromo-1-nitroethenes or alkynyl bromides to form new carbon-carbon bonds.
Addition Reactions
This boronic acid participates in addition reactions with various substrates. Specifically, it reacts with naphthyridine N-oxides, enabling the synthesis of functionalised heterocyclic compounds.
Synthesis of Tetrahydrofuran Derivatives
The compound is employed in oxyarylation reactions of Heck reaction intermediates. This application is crucial for the synthesis of substituted tetrahydrofuran (THF) derivatives, which are prevalent in medicinal chemistry.
Sulfoxidation and Halogenation Processes
4-(Methylthio)phenylboronic acid can be involved in sulfoxidation reactions and copper-catalyzed halogenation processes, expanding its utility in diverse synthetic transformations.
| Molecular weight | 168.02 |
|---|---|
| Linear formula | CH3SC6H4B(OH)2 |
| Impurities tested | <15% anhydride |
| Application | Reactant involved in:• Suzuki-Miyaura cross coupling reactions1 with 2-aryl-1-bromo-1-nitroethenes2 or alkynyl bromides3• Addition reactions with naphthyridine N-oxides4• Oxyarylation of Heck reaction intermediates for synthesis of THF derivatives5• Sulfoxidation reactions6• Copper-catalyzed halogenation7 |
| Melting point | 210-214 °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-(Methylthio)phenylboronic acid used for?
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4-(Methylthio)phenylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions, addition reactions with naphthyridine N-oxides, and in the synthesis of THF derivatives via oxyarylation of Heck reaction intermediates. It is also involved in sulfoxidation and copper-catalyzed halogenation processes.
What are the CAS number and chemical formula for 4-(Methylthio)phenylboronic acid?
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The CAS number for 4-(Methylthio)phenylboronic acid is 98546-51-1, and its linear chemical formula is CH3SC6H4B(OH)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies 4-(Methylthio)phenylboronic acid with an impurity level of <15% anhydride. We do not represent this product as USP/BP/EP grade; it is suitable for research and chemical synthesis purposes.
How should 4-(Methylthio)phenylboronic acid be handled safely?
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Handle 4-(Methylthio)phenylboronic acid with appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter should be used if airborne exposure is possible. It has a WGK rating of 3 in Germany, indicating a higher level of hazard to water.
Is 4-(Methylthio)phenylboronic acid a controlled substance?
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Based on the provided data, there is no indication that 4-(Methylthio)phenylboronic acid is a controlled substance.
How is 4-(Methylthio)phenylboronic acid packed and shipped?
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Tech Serve Solutions exports fine chemicals globally. Packaging and shipping are handled in accordance with international regulations for chemical transport to ensure safe and compliant delivery.
How can I request a quote or sample for 4-(Methylthio)phenylboronic acid?
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To request a quote or sample for 4-(Methylthio)phenylboronic acid, please contact our sales team through the website or by phone, providing your specific requirements.
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