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

Base Information

• Chemical Name: 2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 376584-76-8
• Molecular Formula: C14H17BO2S
• Molecular Weight: 260.165
• Hs Code.: 2934999090
• European Community (EC) Number: 966-764-0
• DSSTox Substance ID: DTXSID20478449
• Nikkaji Number: J1.741.484D
• Wikidata: Q82311839
• Mol file: 376584-76-8.mol

Synonyms:376584-76-8;2-(Benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Benzo(b)thiophene-2-boronic acid, pinacol ester;2-(1-Benzothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Benzo[B]thiophene-2-boronic acid pinacol ester;Benzo[b]thiophene-2-boronic acid pinacol ester;benzo[b]thiophen-2-ylboronic acid pinacol ester;Benzo(b)thiophene-2-boronic acid pinacol ester;SCHEMBL119228;DTXSID20478449;BQA58476;MFCD08063145;AKOS015950205;AS-42751;CS-0092138;EN300-212645;A874044

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

Chemical Property:

• PSA: 46.70000
• LogP: 3.20050
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°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:

NLT 98% ^*data from raw suppliers

Benzo(b)thiophene-2-boronicacid,pinacolester ^*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=CC=CC=C3S2

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

There total 2 articles about 2-(Benzo[b]thiophen-2-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:

bis(pinacol)diborane (73183-34-3) + Benzo[b]thiophene (95-15-8,11095-43-5) → (2-benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-86-6) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene (376584-76-8)

Guidance literature:

With Pt(N,N′-dicyclohexylimidazol-2-ylidene)(divinyltetramethylsiloxane); In n-heptane; at 100 ℃; for 20h; Overall yield = 44 %; Overall yield = 34 mg; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.5b07677

Reference yield:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + Benzo[b]thiophene (95-15-8,11095-43-5) → (2-benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-86-6) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene (376584-76-8)

Guidance literature:

With benzoic acid; In hexane; at 180 ℃; for 16h; Overall yield = 19 percentSpectr.; regioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c00809

Reference yield: 92.0%

trimethyl phosphite (512-56-1) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene (376584-76-8) → 2-Methylbenzothiophene (1195-14-8)

Guidance literature:

With copper(l) iodide; lithium iodide; lithium tert-butoxide; at 50 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jacs.8b10076

upstream raw materials:

bis(pinacol)diborane

Benzo[b]thiophene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

2-(benzo[b]thiophen-2-yl)-5-bromopyridine

C₂₃H₁₈F₃NS₂Si

2-(4-methyl-benzyl)-benzo[b]thiophene

2-(benzothiophen-2-yl)pyridine

Refernces

• 1、 Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto. "C-H borylation by platinum catalysis". . p. 332 - 342. Retrieved 2017/05/09.
• 2、 Takaya, Jun,Ito, Shisei,Nomoto, Hironori,Saito, Narumasa,Kirai, Naohiro,Iwasawa, Nobuharu. "Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex". supporting information. p. 17662 - 17665. Retrieved 2015/12/18.