2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 850881-09-3
• Molecular Formula: C16H27BO2S
• Molecular Weight: 294.266
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30586569
• Nikkaji Number: J2.730.675F
• Wikidata: Q72482433
• Mol file: 850881-09-3.mol

Synonyms:850881-09-3;2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-Hexylthiophene-2-boronic acid pinacol ester;2-(3-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene;3-Hexylthiophene-2-boronic acid, pinacol ester;3-Hexyl-2-thiopheneboronic Acid Pinacol Ester;1,3,2-Dioxaborolane, 2-(3-hexyl-2-thienyl)-4,4,5,5-tetramethyl-;SCHEMBL12264421;DTXSID30586569;XCXAUPBHQCCWCI-UHFFFAOYSA-N;MFCD11045447;AKOS016000708;AS-2529;DB-111506;H1298;A22864;E10051;EN300-7364231;3-Hexylthiophene-2-boronic acid pinacol ester, 95%;3-Hexyl-2-thiopheneboronic acid pinacol ester

Chemical Property of 2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 8.54E-06mmHg at 25°C
• Refractive Index: n20/D 1.492
• Boiling Point: 385.3 °C at 760 mmHg
• Flash Point: 186.8 °C
• PSA: 46.70000
• Density: 1 g/cm³
• LogP: 4.17010
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 294.1824814
• Heavy Atom Count: 20
• Complexity: 304

Purity/Quality:

97% ^*data from raw suppliers

3-Hexyl-2-thiopheneboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CS2)CCCCCC
• Uses: Reagent used for? ;Suzuki-Miyaura cross-coupling reactions1 ? ;p-type/n-type switching of ambipolar bithiazole-benzothiadiazole-based polymers in solar cells1 ? ;Hierarchical self-assembly of semiconductor functionalized peptide a-helixes and optoelectronic properties2 Reagent used in Preparation of? ;Photovoltaic materials, polymers, and thiophene-based compounds with photophysical, electrochemical, and fluorescent properties3,4,5? ;Polymer solar cells for Low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units6 ? ;Dithienothiophene-based dyes Reagent used forSuzuki-Miyaura cross-coupling reactions p-type/n-type switching of ambipolar bithiazole-benzothiadiazole-based polymers in solar cells Hierarchical self-assembly of semiconductor functionalized peptide a-helixes and optoelectronic properties Reagent used in Preparation ofPhotovoltaic materials, polymers, and thiophene-based compounds with photophysical, electrochemical, and fluorescent propertiesPolymer solar cells for Low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units Dithienothiophene-based dyes for dye-sensitized solar cells

Technology Process of 2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 5 articles about 2-(3-Hexylthiophen-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: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) + Triisopropyl borate (5419-55-6) → 3-hexylthiophene-2-boronic acid pinacol ester (850881-09-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; n-BuLi added to soln. of thiophene in THF at -80°C, mixt. stirredat -80.degre.C for 1 h, B(i-PrO)3 added, mixt. allowed to warm to room temp., after 2 h at room temp. pinacol added, suspn. stirred overnight a t room temp.; THF taken off, residue dissolved in petrolether, filtered over neutral alumina, solvent taken off, dried under vac.;

DOI:10.1039/b414817g

Reference yield: 84.0%

3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 3-hexylthiophene-2-boronic acid pinacol ester (850881-09-3)

Guidance literature:

3-hexyl-2-bromothiophene; With magnesium; In diethyl ether; at 20 ℃; for 2h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In diethyl ether; at 20 ℃; for 18h; Further stages.;

DOI:10.1021/ja067879o

Reference yield:

3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) + 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76347-13-2) → 3-hexylthiophene-2-boronic acid pinacol ester (850881-09-3)

Guidance literature:

3-hexyl-2-bromothiophene; With n-butyllithium; In tetrahydrofuran; Inert atmosphere; Schlenk technique;

2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.202113749

upstream raw materials:

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

3-hexyl-2-bromothiophene

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

Triisopropyl borate

Downstream raw materials:

3,4'-dihexyl-2,2'-bithiophene

3,3'-dihexyl-2,2'-bithiophene

Br-HT-Ph₂-HT-Br

4,7-bis-(4-hexyl-thiophen-2-yl)-benzo[1,2,5]thiadiazole