2,2'-Bithiophene-5-boronic acid pinacol ester

Base Information

• Chemical Name: 2,2'-Bithiophene-5-boronic acid pinacol ester
• CAS No.: 479719-88-5
• Molecular Formula: C14H17BO2S2
• Molecular Weight: 292.231
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60393965
• Nikkaji Number: J2.422.550J
• Wikidata: Q72447651
• Mol file: 479719-88-5.mol

Synonyms:479719-88-5;2,2'-Bithiophene-5-boronic acid pinacol ester;2-([2,2'-Bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene;4,4,5,5-tetramethyl-2-(5-thiophen-2-ylthiophen-2-yl)-1,3,2-dioxaborolane;5-(4 4 5 5-TETRAMETHYL-1 3 2-DIOXABOROL&;2-{[2,2'-BITHIOPHEN]-5-YL}-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;SCHEMBL45156;DTXSID60393965;HPOQARMSOPOZMW-UHFFFAOYSA-N;2-(2,2'-Bithiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD04039974;AKOS015898835;AB17467;AS-55606;CS-0091659;T2518;2,2-Bithiophene-5-boronic acid pinacol ester;2,2'-bithiophene-5'-boronic acid pinacol ester;2,2\'-Bithiophene-5-boronic Acid Pinacol Ester;A853654;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborole-2-yl)-2,2'-bithiophene;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 5-(thiophen-2-yl)thiophen-2-yl-2-boronate;2113520-17-3

Chemical Property of 2,2'-Bithiophene-5-boronic acid pinacol ester

Chemical Property:

• Melting Point: 131-136 °C(lit.)
• Refractive Index: n20/D 1.5900(lit.)
• Boiling Point: 406.1±35.0 °C(Predicted)
• Flash Point: 199.4oC
• PSA: 74.94000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 3.77580
• Storage Temp.: 2-8°C(protect from light)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 292.0763023
• Heavy Atom Count: 19
• Complexity: 332

Purity/Quality:

98% ^*data from raw suppliers

2,2′?Bithiophene-5-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(S2)C3=CC=CS3

Technology Process of 2,2'-Bithiophene-5-boronic acid pinacol ester

There total 14 articles about 2,2'-Bithiophene-5-boronic acid pinacol ester 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: 94.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2,2'-Bithiophene (492-97-7) → 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479719-88-5)

Guidance literature:

2,2'-Bithiophene; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1.58333h; Inert atmosphere;

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

DOI:10.1002/adfm.201102519

Reference yield: 86.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-Bithiophene (492-97-7) → 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479719-88-5)

Guidance literature:

2,2'-Bithiophene; With aluminum (III) chloride; boron trichloride; In dichloromethane; at 20 ℃; for 18h;

2,3-dimethyl-2,3-butane diol; With triethylamine; at 20 ℃; for 0.5h;

Reference yield: 86.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-Bithiophene (492-97-7) + boron trichloride (10294-34-5) → 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479719-88-5)

Guidance literature:

With AlCl₃; 2,6-lutidine; In dichloromethane; 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 18 h;

DOI:10.1039/c1cc14226g

upstream raw materials:

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

2,2'-Bithiophene

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

5-bromo(2,2'-bithiophene)

Downstream raw materials:

2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene

N,N'-bis(2,6-diisopropylphenyl)-1-(2,2'-bithiophen-5-yl)-7-(iminohexyl-3,5-bis-dodecyloxybenzoate)perylene-3,4,9,10-tetracarboxydiimide

SP₄T

1,4-bis(2',2-dithienyl)-2,5-bis(decyloxy)benzene