2-(Benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(Benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 501945-71-7
• Molecular Formula: C14H17BO2S
• Molecular Weight: 260.165
• Hs Code.: 2934999090
• European Community (EC) Number: 870-024-1
• DSSTox Substance ID: DTXSID90383677
• Wikidata: Q82175467
• Mol file: 501945-71-7.mol

Synonyms:501945-71-7;2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD05664405;2-DIOXABOROLANE;SCHEMBL451893;DTXSID90383677;YFTHTJAPODJVSL-UHFFFAOYSA-N;BVA94571;1,3,2-Dioxaborolane, 2-benzo[b]thien-5-yl-4,4,5,5-tetramethyl-;AKOS016014234;AB22371;DS-6187;2-(1-BENZOTHIOPHEN-5-YL)-4;CHLOROETHYLCLONIDINEDIHYDROCHLORIDE;SY101392;CS-0041352;Benzo[b]thiophene-5-boronic Acid Pinacol Ester;EN300-197953;F19711;BENZOTHIOPHENE-5-BORONIC ACID PINACOL ESTER;J-000006;J-506210;Z1972712516;1-benzothiophen-5-yl-4,4,5,5tetramethyl-1,3,2-dioxaborolane;1-benzothiophen-5-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-benzo[b]thiophen-5-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(1-benzothiophen-5-yl)-4,4,5,5-tetra-methyl-1,3,2-dioxaborolane;benzo[b]thiophene,4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-;2-(1-BENZOTHIOPHEN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE,95%

Chemical Property of 2-(Benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 1.44E-05mmHg at 25°C
• Melting Point: 118 °C
• Refractive Index: 1.57
• Boiling Point: 377.7°C at 760 mmHg
• Flash Point: 182.2°C
• PSA: 46.70000
• Density: 1.13g/cm³
• LogP: 3.20050
• 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: 1
• Exact Mass: 260.1042311
• Heavy Atom Count: 18
• Complexity: 316

Purity/Quality:

98%min ^*data from raw suppliers

2-(Benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*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)C2=CC3=C(C=C2)SC=C3

Technology Process of 2-(Benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 8 articles about 2-(Benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-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: 92.0%

5-bromobenzo[b]thiophene (4923-87-9) + bis(pinacol)diborane (73183-34-3) → 2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (501945-71-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,2-dichloro-ethane; at 80 ℃; for 18h;

DOI:10.1021/acs.joc.9b01844

Reference yield: 79.0%

→ 2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (501945-71-7)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 4h; Inert atmosphere;

Reference yield: 71.0%

5-chlorobenzothiophene (20532-33-6) + bis(pinacol)diborane (73183-34-3) → 2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (501945-71-7)

Guidance literature:

With caesium carbonate; cesium fluoride; (5-tert-butyl-2-hydroxyphenyl)diphenylphosphine; In dimethyl sulfoxide; at 20 ℃; for 22h; Irradiation;

DOI:10.1021/acscatal.1c05941

upstream raw materials:

5-bromobenzo[b]thiophene

bis(pinacol)diborane

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

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

Downstream raw materials:

1-{1-[5-(benzo[b]thien-5-yl)-thien-2-yl]cyclohexyl}pyrrolidine

3-benzo[b]thiophen-5-yl-1-benzyl-pyrrolidine-2,5-dione

benzo[b]thiophen-5-ylboronic acid

1-{2-[4-(2-benzo[b]thiophen-5-yl-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidine

Refernces

• 1、 Ji, Shuohan,Qin, Shengxiang,Yin, Chunyu,Luo, Lu,Zhang, Hua. "Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation". supporting information. p. 64 - 68. Retrieved 2021/12/27.
• 2、 Kim, Hyunwoo,Kim, Hyungjun,Lambert, Tristan H.,Lin, Song. "Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials". supporting information. p. 2087 - 2092. Retrieved 2020/02/04.