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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(4-(methylthio)phenyl)-1,3,2-dioxaborolane
• CAS No.: 190788-58-0
• Molecular Formula: C13H19 B O2 S
• Molecular Weight: 250.17
• Hs Code.: 2934999090
• European Community (EC) Number: 941-101-8,808-573-6
• DSSTox Substance ID: DTXSID60590412
• Nikkaji Number: J845.356J
• Wikidata: Q72491542
• Mol file: 190788-58-0.mol

Synonyms:190788-58-0;4,4,5,5-Tetramethyl-2-(4-(methylthio)phenyl)-1,3,2-dioxaborolane;4-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE;4-Methylthiophenylboronic acid, pinacol ester;4-(Methylthio)phenylboronic acid pinacol ester;4,4,5,5-tetramethyl-2-[4-(methylsulfanyl)phenyl]-1,3,2-dioxaborolane;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-[4-(METHYLTHIO)PHENYL]-;4-methylthiophenylboronic acid,pinacol ester;4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-1,3,2-dioxaborolane;4-THIOANISOLEBORONIC ACID, PINACOL ESTER;4-Methylthiophenylboronic acid pinacol ester;SCHEMBL12538851;DTXSID60590412;MFCD05155222;AKOS015960122;AB21553;AS-2629;DB-016041;CS-0130293;H11390;EN300-1425841;A813442;J-012326;4-Thioanisoleboronic acid, pinacol ester, AldrichCPR;4-(methylthio)phenylboronic acid pinacolate, AldrichCPR;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-thioanisole

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

Chemical Property:

• Vapor Pressure: 0.00013mmHg at 25°C
• Melting Point: 35.1-35.9 °C
• Refractive Index: 1.525
• Boiling Point: 344.5°C at 760 mmHg
• Flash Point: 162.2°C
• PSA: 43.76000
• Density: 1.06g/cm³
• LogP: 2.70770
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 250.1198812
• Heavy Atom Count: 17
• Complexity: 257

Purity/Quality:

97% ^*data from raw suppliers

4-(Methylthio)phenylboronicAcidPinacolEster ^*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=C(C=C2)SC

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

There total 18 articles about 4,4,5,5-Tetramethyl-2-(4-(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: 94.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (4-thiomethoxyphenyl)boronic acid (98546-51-1) → 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane (190788-58-0)

Guidance literature:

2,3-dimethyl-2,3-butane diol; (4-thiomethoxyphenyl)boronic acid; In toluene; Reflux;

for 2h; Molecular sieve; Heating;

DOI:10.1021/jo2001808

Reference yield: 87.0%

1-[4-(methylsulfanyl)phenyl]diazonium tetrafluoroborate + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane (190788-58-0)

Guidance literature:

With zinc(II) perchlorate; In methanol; at 40 ℃; Inert atmosphere;

DOI:10.1002/open.201700036

Reference yield: 86.1%

S-ethyl 4-methylthiobenzothioate + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane (190788-58-0)

Guidance literature:

With [Rh(OH)(cod)]2; tributylphosphine; potassium acetate; at 80 ℃; for 24h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201611974

upstream raw materials:

Phenyl triflate

4-(methylthio)phenyl trifluoromethanesulfonate

2,3-dimethyl-2,3-butane diol

(4-bromophenyl)thioanisole

Downstream raw materials:

8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(18-azacrown-6-N-carbonylmethoxy)-p-octiphenyl

1⁴-2'-t-Boc-aminoethylthio-8⁴-methylthio-7³,6²,5³,4²,3³,2²-hexa(18-aza-6-N-carbonylmethoxy)-p-octiphenyl

8⁴,1⁴-dimethylsulfanyl-7³,6²,5³,4²,3³,2²-hexa(tert-butoxycarbonylmethoxy)-p-octiphenyl

methyl 4-(methylthio)benzoate