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

Base Information

• Chemical Name: 2-(Benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 171364-86-6
• Molecular Formula: C14H19BO3S
• Molecular Weight: 260.165
• DSSTox Substance ID: DTXSID80443173
• Wikidata: Q82260883
• Mol file: 171364-86-6.mol

Synonyms:171364-86-6;2-(Benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-Benzothiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Benzo[b]thiophen-3-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(Benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;Benzo[b]thiophene-3-boronic acid pinacol ester;Benzo[b]thiophene, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL574089;DTXSID80443173;WGA36486;2-Benzo[b]thiophen-3-yl-4,4,5,5-tetramethyl-1,3,2-dioxaboro lane;MFCD11110552;AKOS016007121;SB34222;AS-78113;B5821;CS-0091569;FT-0727436;D71590;EN300-4698445;A881933;2-Benzo[b]thiophen-3-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-benzo[b]thiophen-3-yl-[1,3,2]dioxaborolane

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

Chemical Property:

• Boiling Point: 377.7±15.0 °C(Predicted)
• PSA: 46.70000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.20050
• Storage Temp.: 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:

97% ^*data from raw suppliers

2-Benzo[b]thiophen-3-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=CSC3=CC=CC=C23

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

There total 11 articles about 2-(Benzo[b]thiophen-3-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: 96.0%

3-Bromothianaphthene (7342-82-7) + bis(pinacol)diborane (73183-34-3) → (2-benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-86-6)

Guidance literature:

With C₅₄H₄₄NO₂PPdS; potassium acetate; In 2-methyltetrahydrofuran; at 90 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b02414

Reference yield: 78.0%

3-Bromothianaphthene (7342-82-7) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → (2-benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-86-6)

Guidance literature:

3-Bromothianaphthene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/ol802969b

Reference yield: 54.0%

(E)-1-(benzo[b]thiophen-3-yl)butan-1-one O-perfluorobenzoyl oxime + bis(pinacol)diborane (73183-34-3) → (2-benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-86-6)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; palladium dichloride; In 1,2-dichloro-ethane; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.202006740

upstream raw materials:

3-Bromothianaphthene

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

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Downstream raw materials:

C₂₆H₁₇NOS₃

4,5-di(benzo[b]thiophen-3-yl)-2-phenylthiazole

4-(benzo[b]thiophen-3-yl)-5-(2-ethoxybenzo[b]thiophen-3-yl)-2-phenylthiazole