98546-51-1

Basic information

• Product Name: 4-(Methylthio)phenylboronic acid
• Synonyms: 4-THIOMETHYLPHENYLBORONIC ACID;4-THIOANISOLEBORONIC ACID;4-(METHYLSULFANYL)PHENYLBORONIC ACID;4-METHYLSULFANYL-BENZENEBORONIC ACID;4-(METHYLTHIO)BENZENEBORONIC ACID;4-(METHYLTHIO)PHENYLBORONIC ACID;4-(METHYLMERCAPTO)BENZENEBORONIC ACID;4-BORONOTHIOANISOLE
• CAS NO: 98546-51-1
• Molecular Formula: C₇H₉BO₂S
• Molecular Weight: 168.02
• Product Categories: Organometallic Reagents;Boronate Ester;Potassium Trifluoroborate;Azoles;blocks;BoronicAcids;Boric Acid;Boronic acids;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);organic or inorganic borate;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Monosubstituted Aryl Boronic Acids
• Mol File: 98546-51-1.mol

Chemical Properties

• Melting Point: 210-214 °C(lit.)
• Boiling Point: 333.5 °C at 760 mmHg
• Flash Point: 155.5 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.22 g/cm³
• Vapor Pressure: 5.41E-05mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 8.56±0.10(Predicted)
• BRN: 3247219
• CAS DataBase Reference: 4-(Methylthio)phenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Methylthio)phenylboronic acid(98546-51-1)
• EPA Substance Registry System: 4-(Methylthio)phenylboronic acid(98546-51-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-7/9
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 98546-51-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(Methylthio)phenylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions for the synthesis of biologically active compounds and pharmaceutical agents. Its ability to form carbon-carbon bonds with 2-aryl-1-bromo-1-nitroethenes or alkynyl bromides allows for the creation of diverse molecular structures with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(Methylthio)phenylboronic acid is used as a reactant in addition reactions with naphthyridine N-oxides. This reaction contributes to the formation of new chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in the Synthesis of THF Derivatives:
4-(Methylthio)phenylboronic acid is utilized as a reactant in the oxyarylation of Heck reaction intermediates, leading to the synthesis of tetrahydrofuran (THF) derivatives. These derivatives are valuable intermediates in the preparation of various organic compounds and have applications in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Sulfur Chemistry:
In sulfur chemistry, 4-(Methylthio)phenylboronic acid is employed in sulfoxidation reactions, which are crucial for the synthesis of various sulfur-containing compounds. These compounds have applications in the development of new drugs, agrochemicals, and other specialty chemicals.
Used in Halogenation Reactions:
4-(Methylthio)phenylboronic acid is used as a reactant in copper-catalyzed halogenation reactions, which are essential for the introduction of halogen atoms into organic molecules. This modification can enhance the reactivity, stability, and biological activity of the resulting compounds, making them suitable for various applications in the pharmaceutical, agrochemical, and materials science industries.

InChI:InChI=1/C7H9BO2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3

Upstream product

• 5419-55-6 Triisopropyl borate 
• 104-95-0 (4-bromophenyl)thioanisole 
• 121-43-7 Trimethyl borate 
• 166386-48-7 (4-(methylsulfinyl)phenyl)boronic acid 
• 13675-18-8 tetrahydroxydiboron 
• 60822-47-1 4-bromothio-anisole 
• 77-92-9 citric acid 
• 237429-34-4 4-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid 
• 153312-70-0 (4-bromophenylsulfanyl)-tert-butyldimethylsilane 
• 106-53-6 para-bromobenzenethiol 
• 237429-33-3 4-mercaptophenylboronic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 603950-57-8 5-tert-butyl-4'-(2-diphenylphosphanylethylsulfanyl)-4-hydroxybiphenyl-3-carbaldehyde 
• 487047-30-3 3-chloro-4-(4'-methylthiophenyl)-5H-furan-2-one 
• 162012-28-4 4-(4-(methylthio)phenyl)furan-2(5H)-one 
• 213764-19-3 2-benzyl-4-bromo-5-(4-methylthiophenyl)pyridazin-3(2H)-one 
• 57666-97-4 5-(4-methylsulfanylphenyl)furan-2-carbaldehyde 
• 488759-34-8 1-[2-(4-methylsulfanyl-phenyl)-cyclopent-1-enyl]-ethanone O-benzo[1,3]dioxol-5-ylmethyl-oxime 
• 488759-26-8 2-(4-methylsulfanyl-phenyl)-cyclopent-1-enecarbaldehyde O-benzo[1,3]dioxol-5-ylmethyl-oxime 
• 499140-48-6 (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-(4-(methylthio)phenyl)-3-oxolen-2-one 
• 493021-74-2 2-(4-methylsulfanyl-phenyl)-cyclopent-1-enecarbaldehyde O-(2-chloro-6-fluoro-benzyl)-oxime 
• 493021-71-9 2-(4-methylsulfanyl-phenyl)-cyclopent-1-enecarbaldehyde O-(4-methoxy-benzyl)-oxime 
• 493021-72-0 2-(4-methylsulfanyl-phenyl)-cyclopent-1-enecarbaldehyde O-(4-fluoro-benzyl)-oxime 

Relevant articles and documents

Gold-Carbon Contacts from Oxidative Addition of Aryl Iodides

Aryl halides are ubiquitous functional groups in organic chemistry, yet despite their obvious appeal as surface-binding linkers and as precursors for controlled graphene nanoribbon synthesis, they have seldom been used as such in molecular electronics. The confusion regarding the bonding of aryl iodides to Au electrodes is a case in point, with ambiguous reports of both dative Au-I and covalent Au-C contacts. Here we form single-molecule junctions with a series of oligophenylene molecular wires terminated asymmetrically with iodine and thiomethyl to show that the dative Au-I contact has a lower conductance than the covalent Au-C interaction, which we propose occurs via an in situ oxidative addition reaction at the Au surface. Furthermore, we confirm the formation of the Au-C bond by measuring an analogous series of molecules prepared ex situ with the complex AuI(PPh3) in place of the iodide. Density functional theory-based transport calculations support our experimental observations that Au-C linkages have higher conductance than Au-I linkages. Finally, we demonstrate selective promotion of the Au-C bond formation by controlling the bias applied across the junction. In addition to establishing the different binding modes of aryl iodides, our results chart a path to actively controlling oxidative addition on an Au surface using an applied bias.

In Situ Formation of N-Heterocyclic Carbene-Bound Single-Molecule Junctions

Self-assembled monolayers (SAMs) formed using N-heterocyclic carbenes (NHCs) have recently emerged as thermally and chemically ultrastable alternatives to those formed from thiols. The rich chemistry and strong σ-donating ability of NHCs offer unique pros

Base free Suzuki acylation reactions of sodium (aryl trihydroxyborate) salts: A novel synthesis of substituted aryl ketones

The first simple and efficient base free Pd(PPh3)4 catalysed synthesis of substituted aryl ketones from acyl chlorides and easily accessible sodium aryl trihydroxyborate salts in aqueous toluene is reported. The reaction conditions appeared versatile and tolerable to a variety of functional groups including, CF3, OMe, SMe, Br, NO2, F, OH and NH2 furnishing 25 examples of substituted aryl ketones in isolated yields of up to 96% in 24 h. Beside the high purity, the ease and convenience of the isolation compared to boronic acids, sodium aryl trihydroxyborate salts could be used subsequently without the addition of excess amount of an activator and are more user-friendly in terms of the use of accurate reaction stoichiometry.

B(C6F5)3-Catalyzed Deoxygenation of Sulfoxides and Amine N-Oxides with Hydrosilanes

An efficient strategy for the deoxygenation of sulfoxides and amine N-oxides by using B(C6F5)3 and hydrosilanes was developed. This method provided the corresponding aromatic and aliphatic products in good to high yields and showed good functional-group tolerance under mild conditions.

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

Synthesis of dihydroindolizines for potential photoinduced work function alteration

Seeking to immobilize photochromophores on metallic surfaces, we have synthesized four molecules which contain both a photoresponsive dihydroindolizine (DHI) core and a sulfur containing moiety, which allow for their assembly onto gold substrates. Sonogashira, Suzuki, or Ullmann couplings are employed to generate pyridines with pendant thioacetates (or disulfides). The pyridines are condensed with spiro[2-cyclopropene-1, 9′-[9H]fluorene]- 2, 3-dimethyl ester affording the targeted DHIs.

1-Methylpyridinium-4-(4-phenylmethanethiosulfonate) iodide, MTS-MPP+, a novel scanning cysteine accessibility method (SCAM) reagent for monoamine transporter studies

A novel substituted cysteine accessibility method (SCAM) reagent was developed for monoamine uptake transporters. The new reagent, MTS-MPP+, was a derivative of the neurotoxin and transporter substrate MPP+. MTS-MPP+ label

Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them

The present invention provides, among other things, new bicyclo heterocyclic compounds, compositions comprising these heterocyclic compounds, methods of making the heterocyclic compounds, and methods of using these heterocyclic compounds for treating a variety of conditions and disease states associated with, for example, cellular proliferation, inflammation, glycosidase expression, or the low expression of Perlecan.

Formation of boroxine: Its stability and thermodynamic parameters in solution

Condensation of three boronic acids proceeding at room temperature gave their corresponding boroxines; NMR spectral measurements revealed that the reaction was reversible at room temperature, that electron-donating groups supported the formation of boroxine, and that entropically driven forces promoted the formation of boroxine in solution.

Synthesis of functional aromatic multisulfonyl chlorides and their masked precursors

The synthesis of functional aromatic bis(sulfonyl chlorides) containing an acetophenone and two sulfonyl chloride groups, i.e., 3,5-bis[4-(chlorosulfonyl)phenyl]-1-acetophenone (16), 3,5-bis(chlorosulfonyl)-1-acetophenone (17), and 3,5-bis(4-(chlorosulfonyl)phenyloxy)-1-acetophenone (18) via a sequence of reactions, involving in the last step the quantitative oxidative chlorination of S-(aryl)-N,N′-diethylthiocarbamate, alkyl- or benzyl thiophenyl groups as masked nonreactive precursors to sulfonyl chlorides is described. A related sequence of reactions was used for the synthesis of the aromatic trisulfonyl chloride 1,1,1-tris(4-chlorosulfonylphenyl)ethane (24). 4-(Chlorosulfonyl)phenoxyacetic acid, 2,2-bis[[[4-(chlorosulfonyl)phenoxyacetyl]oxy]methyl]-1,3-propanediyl ester (27), 5,11,17,23-tetrakis(chlorosulfonyl)-25,26,27,28-tetrakis (ethoxycarbonylmethoxy)calix[4]arene (38), 5,11,17,23,29,35-hexakis(chlorosulfonyl)-37,38,39,40,41,42-hexakis (ethoxycarbonylmethoxy)calix[6]arene (39), 5,11,17,23,29,35,41,47-octakis (chlorosulfonyl)-49,50,51,52,53,54,55,56-octakis(ethoxycarbonylmethoxy) calix[8]arene (40), 5,11,17,23-tetrakis(tert-butyl)-25,26,27,28-tetrakis(chlorosulfonyl phenoxyacetoxy)calix[4]arene (44), 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41,42-hexakis (chlorosulfonylphenoxyacetoxy)calix[6]arene (45), and 5,11,17,23,29,35,41,47-octakis (tert-butyl)-49,40,51,52,53,54,55,56-octakis (chlorosulfonylphenoxyacetoxy)calix[8]arene (46) were synthesized by two different multistep reaction procedures, the last step of both methods consisting of the chlorosulfonation of compounds containing suitable activated aromatic positions. 2,4,6-Tris(chlorosulfonyl)aniline (47) was obtained by the chlorosulfonation of aniline. The conformation of two series of multisulfonyl chlorides i.e., 38, 39, 40 and 44, 45, 46, was investigated by 1H NMR spectroscopy. The masked nonreactive precursor states of the functional aromatic multisulfonyl chlorides and the aromatic multisulfonyl chlorides reported here represent the main starting building blocks required in a new synthetic strategy elaborated for the preparation of dendritic and other complex organic molecules.