4,4,5,5-Tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane
• CAS No.: 1072945-09-5
• Molecular Formula: C13H19BO2S
• Molecular Weight: 250.17
• Hs Code.: 2934999090
• European Community (EC) Number: 808-436-0
• DSSTox Substance ID: DTXSID70590403
• Wikidata: Q82484104
• Mol file: 1072945-09-5.mol

Synonyms:1072945-09-5;4,4,5,5-Tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane;2-Methylthiophenylboronic acid, pinacol ester;2-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE;4,4,5,5-TETRAMETHYL-2-(2-METHYLSULFANYLPHENYL)-1,3,2-DIOXABOROLANE;2-METHYLSULFANYLPHENYLBORONIC ACID, PINACOL ESTER;4,4,5,5-Tetramethyl-2-[2-(methylsulfanyl)phenyl]-1,3,2-dioxaborolane;2-Methylthiophenylboronic acid pinacol ester;SCHEMBL13125445;DTXSID70590403;SLJWZEVOGXSTOM-UHFFFAOYSA-N;MFCD05155219;AKOS015960123;AB21549;BS-25984;CS-0175680;D71348;EN300-1706410;A895592;J-001768;2-methylsulfanylphenylboronic acid, pinacol ester, AldrichCPR

Chemical Property of 4,4,5,5-Tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 77.5-78.6 °C
• Boiling Point: 340.9±25.0 °C(Predicted)
• PSA: 43.76000
• Density: 1.06±0.1 g/cm3(Predicted)
• LogP: 2.70770
• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 250.1198812
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

98%min ^*data from raw suppliers

2-MethylsulfanylphenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2SC

Technology Process of 4,4,5,5-Tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane

There total 6 articles about 4,4,5,5-Tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane 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: 82.0%

methyl-phenyl-thioether (100-68-5) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane (1072945-09-5)

Guidance literature:

bis(pinacol)diborane; With 5-methyl-2-(thiophen-3-yl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 20 ℃; for 0.0333333h; Inert atmosphere; Glovebox;

methyl-phenyl-thioether; In tetrahydrofuran; at 60 ℃; for 24h; Reagent/catalyst; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.0c13415

Reference yield: 54.0%

bis(pinacol)diborane (73183-34-3) + 2-(methylthio)benzoic acid (3724-10-5) → 4,4,5,5-tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane (1072945-09-5)

Guidance literature:

With dmap; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane; In 1,4-dioxane; at 160 ℃; for 15h;

DOI:10.1002/anie.201810145

Reference yield:

methyl-phenyl-thioether (100-68-5) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2-(methylthio)phenyl)-1,3,2-dioxaborolane (1072945-09-5) + 4,4,5,5‐tetramethyl‐2‐[3‐(methylsulfanyl)phenyl]‐1,3,2‐dioxaborolane (710348-63-3) + 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane (190788-58-0)

Guidance literature:

With 4,4'-dimethyl-2,2'-bipyridines; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In para-xylene; at 55 ℃; for 24h; Solvent; Overall yield = 70 %; Overall yield = 88 mg; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201610041

upstream raw materials:

methyl-phenyl-thioether

[Rh{B(pinacolato)₂}(PEt₃)₃]

bis(pinacol)diborane

2-(methylthio)benzoic acid

Downstream raw materials:

2-(methylthio)-1-(trifluoromethyl)benzene

1-methoxy-2-(methylsulfanyl)benzene

2-bromo-1-(methylsulfanyl)benzene

methyl o-tolyl sulfide

Refernces

• 1、 Kuninobu, Yoichiro,Naito, Morio,Torigoe, Takeru,Yamanaka, Masahiro,Zeng, Jialin. "Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand". supporting information. . Retrieved 2020/05/08.
• 2、 Li, Hong Liang,Kuninobu, Yoichiro,Kanai, Motomu. "Lewis Acid–Base Interaction-Controlled ortho-Selective C?H Borylation of Aryl Sulfides". supporting information. p. 1495 - 1499. Retrieved 2017/02/05.