4,4,5,5-Tetramethyl-2-[(phenylsulfanyl)methyl]-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-[(phenylsulfanyl)methyl]-1,3,2-dioxaborolane
• CAS No.: 66080-23-7
• Molecular Formula: C13H19BO2S
• Molecular Weight: 250.17
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40405494
• Nikkaji Number: J1.601.077D
• Wikidata: Q82210071
• Mol file: 66080-23-7.mol

Synonyms:66080-23-7;4 4 5 5-TETRAMETHYL-2-PHENYLSULFANYLMET&;4,4,5,5-tetramethyl-2-(phenylsulfanylmethyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-[(phenylsulfanyl)methyl]-1,3,2-dioxaborolane;4,4,5,5,-Tetramethyl-2-phenylsulfanylmethyl-1,3,2-dioxaborolane;SCHEMBL8320437;DTXSID40405494;EN300-6253638;Z2049747172;2-((Phenylthio)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5,-Tetramethyl-2-phenylsulfanylmethyl-1,3,2-dioxaborolane, 97%

Chemical Property of 4,4,5,5-Tetramethyl-2-[(phenylsulfanyl)methyl]-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00197mmHg at 25°C
• Refractive Index: n20/D 1.5280(lit.)
• Boiling Point: 105-108oC0.1 mm Hg(lit.)
• Flash Point: 221 °F
• PSA: 43.76000
• Density: 1.059 g/mL at 25oC(lit.)
• LogP: 3.82840
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 250.1198812
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

4,4,5,5,-Tetramethyl-2-phenylsulfanylmethyl-1,3,2-dioxaborolane 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CSC2=CC=CC=C2
• Uses: 4,4,5,5,-Tetramethyl-2-phenylsulfanylmethyl-1,3,2-dioxaborolane is used to prepare aryl/heteroaryl derivatives via the formation of C-C and C-hetero bonds.It can also be used as:A starting material in the synthesis of α-aminoboronic acids as serine proteases inhibitors.A substrate in the coupling reactions with carbonyl compounds under Ir-catalyzed photoredox conditions.

Technology Process of 4,4,5,5-Tetramethyl-2-[(phenylsulfanyl)methyl]-1,3,2-dioxaborolane

There total 3 articles about 4,4,5,5-Tetramethyl-2-[(phenylsulfanyl)methyl]-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: 68.0%

trimethyl((phenylthio)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)silane → 4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane (66080-23-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1.5h; Sealed tube; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01840

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + (phenylthio)methaneboronic acid (67975-88-6) → 4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane (66080-23-7)

Guidance literature:

In diethyl ether;

DOI:10.1021/ja00472a066

Reference yield:

4,4,5,5-tetramethyl-2-(phenylthio)-1,3,2-dioxaborolane (1443045-55-3) → 4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane (66080-23-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hexane / 6 h / 50 °C / Glovebox; Schlenk technique; Inert atmosphere; Sealed tube

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 25 °C / Sealed tube; Schlenk technique; Inert atmosphere

With tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane;

DOI:10.1021/acs.orglett.6b01840

upstream raw materials:

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

(phenylthio)methaneboronic acid

4,4,5,5-tetramethyl-2-(phenylthio)-1,3,2-dioxaborolane

Downstream raw materials:

2-hydroxy-3-(phenylthio)-1,2-oxaborolane

4,4,5,5-tetramethyl-2-[4-(2-methyl-[1,3]dioxolan-2-yl)-1-phenylsulfanyl-butyl]-[1,3,2]dioxaborolane

4-oxo-5-phenylthiopentanoic acid

2,2-diphenyl-1-phenylthioethene