4-(Methylthio)phenylboronic acid

Base Information

• Chemical Name: 4-(Methylthio)phenylboronic acid
• CAS No.: 98546-51-1
• Molecular Formula: C7H9BO2S
• Molecular Weight: 168.024
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID00370058
• Nikkaji Number: J1.049.855D
• Wikidata: Q72491528
• ChEMBL ID: CHEMBL162340
• Mol file: 98546-51-1.mol

Synonyms:4-(Methylthio)phenylboronic acid;98546-51-1;4-Thioanisoleboronic acid;4-methylthiophenylboronic acid;(4-methylsulfanylphenyl)boronic Acid;4-(methylsulfanyl)phenylboronic acid;4-(Methylthio)benzeneboronic acid;4-(Methylthio)phenylboronicacid;MFCD00093410;(4-(methylthio)phenyl)boronic acid;Boronic acid, [4-(methylthio)phenyl]-;4-(methylthio)benzene boronic acid;[4-(methylsulfanyl)phenyl]boronic acid;(4-(methylthio)phenyl]boronic acid;[4-(methylthio)phenyl]boronic acid;4-(METHYLMERCAPTO)BENZENEBORONIC ACID;SCHEMBL184212;4-methylthiophenyl-boronic acid;CHEMBL162340;4- methylthiophenyl boronic acid;4-methylthio phenyl boronic acid;DTXSID00370058;4-(methyl-thio)phenylboronic acid;4-(methylthio)phenyl boronic acid;IVUHTLFKBDDICS-UHFFFAOYSA-N;4-(methylthio) benzeneboronic acid;4-methylsulfanyl-phenylboronic acid;4-methylsulfanylphenyl boronic acid;4-methylsulphanyl-phenylboronic acid;CS-D1041;4-methylsulfanyl phenyl boronic acid;4-methylsulfanyl-phenyl boronic acid;4-(methylsulfanyl)phenyl-boronic acid;AKOS000279153;AB03347;AC-5369;AS-2624;[4-(methylsulphanyl)phenyl]boronic acid;NCGC00249472-01;BP-12658;SY026617;Boronic acid, B-[4-(methylthio)phenyl]-;4-(METHYLSULFANYL)BENZENEBORONIC ACID;AM20080730;FT-0602404;M1458;EN300-140385;J-501323;Z381540922;4-(methylthio)phenylboronic acid

Chemical Property of 4-(Methylthio)phenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 5.41E-05mmHg at 25°C
• Melting Point: 210-214 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 333.5 °C at 760 mmHg
• PKA: 8.56±0.10(Predicted)
• Flash Point: 155.5 °C
• PSA: 65.76000
• Density: 1.22 g/cm³
• LogP: 0.08830
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.0416309
• Heavy Atom Count: 11
• Complexity: 113

Purity/Quality:

99% ^*data from raw suppliers

4-Methylthiophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)SC)(O)O
• Uses: 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 suzuki reaction Reactant involved in:Suzuki-Miyaura cross coupling reactions with 2-aryl-1-bromo-1-nitroethenes or alkynyl bromidesAddition reactions with naphthyridine N-oxidesOxyarylation of Heck reaction intermediates for synthesis of THF derivativesSulfoxidation reactionsCopper-catalyzed halogenation

Technology Process of 4-(Methylthio)phenylboronic acid

There total 14 articles about 4-(Methylthio)phenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

Triisopropyl borate (5419-55-6) + (4-bromophenyl)thioanisole (104-95-0) → (4-thiomethoxyphenyl)boronic acid (98546-51-1)

Guidance literature:

(4-bromophenyl)thioanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jacs.8b05184

Reference yield: 81.0%

(4-(methylsulfinyl)phenyl)boronic acid (166386-48-7) → (4-thiomethoxyphenyl)boronic acid (98546-51-1)

Guidance literature:

With tris(pentafluorophenyl)borate; phenylsilane; In toluene; at 60 ℃; for 8h; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1002/ejoc.201700489

Reference yield: 79.0%

tetrahydroxydiboron (13675-18-8) + (4-bromophenyl)thioanisole (104-95-0) → (4-thiomethoxyphenyl)boronic acid (98546-51-1)

Guidance literature:

In methanol; at 15 ℃; for 3h; Microwave irradiation;

DOI:10.1021/jacs.6b01376

upstream raw materials:

4-mercaptophenylboronic acid

methyl iodide

(4-bromophenyl)thioanisole

para-bromobenzenethiol

Downstream raw materials:

1-(2-bromocyclopenten-1-yl)-4-(methylthio)benzene

3-[4-(methylthio)phenyl]thiophene

3-Bromo-4-(4-methylsulfanyl-phenyl)-thiophene

4′-(methylthio)-[1,1′-biphenyl]-2-amine

Refernces

• 1、 Doud, Evan A.,Inkpen, Michael S.,Lovat, Giacomo,Montes, Enrique,Paley, Daniel W.,Steigerwald, Michael L.,Vázquez, Héctor,Venkataraman, Latha,Roy, Xavier. "In Situ Formation of N-Heterocyclic Carbene-Bound Single-Molecule Junctions". supporting information. p. 8944 - 8949. Retrieved 2018/07/29.
• 2、 Sithebe, Siphamandla,Molefe, Patience. "Base free Suzuki acylation reactions of sodium (aryl trihydroxyborate) salts: A novel synthesis of substituted aryl ketones". . p. 305 - 311. Retrieved 2017/07/13.