4,4,5,5-Tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolane
• CAS No.: 214360-70-0
• Molecular Formula: C10H15BO2S
• Molecular Weight: 210.105
• Hs Code.: 2934999090
• European Community (EC) Number: 674-923-8
• DSSTox Substance ID: DTXSID10375251
• Nikkaji Number: J1.304.183K
• Wikidata: Q72508800
• Mol file: 214360-70-0.mol

Synonyms:214360-70-0;thiophene-3-boronic acid pinacol ester;4,4,5,5-tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(3-thienyl)-1,3,2-dioxaborolane;thiophene-3-boronic acid, pinacol ester;4,4,5,5-tetramethyl-2-thiophen-3-yl-1,3,2-dioxaborolane;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene;MFCD05663893;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-thiophene;3-Thiopheneboronic acid pinacol ester;Thiophene-3-boronic acid pinacal ester;SCHEMBL1033417;DTXSID10375251;HQXQOBAEDQBINI-UHFFFAOYSA-N;AKOS015950768;AB22039;AS-2654;SY122156;CS-0043239;FT-0643974;EN300-262828;THIOPHEN-3-YLBORONIC ACID PINACOL ESTER;3-Thienylboronic acid 2,3-dimethyl-2,3-butanediyl;J-513984;Z1269204423;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(3-thienyl)-;4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene, AldrichCPR

Chemical Property of 4,4,5,5-Tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00452mmHg at 25°C
• Melting Point: 72-73 °C
• Refractive Index: 1.501
• Boiling Point: 286.547 °C at 760 mmHg
• Flash Point: 127.099 °C
• PSA: 46.70000
• Density: 1.075 g/cm³
• LogP: 2.04730
• 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: 210.0885811
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

98% ^*data from raw suppliers

3-ThiopheneboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CSC=C2

Technology Process of 4,4,5,5-Tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolane

There total 22 articles about 4,4,5,5-Tetramethyl-2-(thiophen-3-yl)-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: 97.0%

3-Bromothiophene (872-31-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane (214360-70-0)

Guidance literature:

With potassium acetate; palladium diacetate; (1R,3S,5S,7R)-8-Cyclohexyl-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantane; In tetrahydrofuran; at 70 ℃; for 12h; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tetlet.2021.153572

Reference yield: 95.0%

3-thienyl iodide (10486-61-0) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane (214360-70-0)

Guidance literature:

bis(pinacol)diborane; With diethylzinc; sodium t-butanolate; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.5h; Schlenk technique; Glovebox; Inert atmosphere;

3-thienyl iodide; In tetrahydrofuran; hexane; at 20 - 75 ℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/ja409748m

Reference yield: 95.0%

3-Bromothiophene (872-31-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane (214360-70-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; Flow reactor;

DOI:10.1002/chem.201303736

upstream raw materials:

Thien-3-ylboronic acid

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

3-Bromothiophene

bis(pinacol)diborane

Downstream raw materials:

methyl (E)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(3-thienyl)acetate

phenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)iodonium tosylate

pinacol 2,5-dibromo-3-thiopheneylboronate

3-(4-tolyl)thiophene

Refernces

• 1、 Lamola, Jairus L.,Moshapo, Paseka T.,Holzapfel, Cedric W.,Christopher Maumela, Munaka. "Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands". supporting information. . Retrieved 2021/12/13.
• 2、 Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul. "Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates". supporting information. p. 5022 - 5037. Retrieved 2021/05/04.