2,2'-Bithiophene-5-boronic acid

Base Information

• Chemical Name: 2,2'-Bithiophene-5-boronic acid
• CAS No.: 132898-95-4
• Molecular Formula: C8H7BO2S2
• Molecular Weight: 210.085
• Hs Code.: 2934999090
• European Community (EC) Number: 848-600-9
• DSSTox Substance ID: DTXSID90380065
• Nikkaji Number: J1.976.353F
• Wikidata: Q82170097
• Mol file: 132898-95-4.mol

Synonyms:132898-95-4;2,2'-Bithiophene-5-boronic acid;[2,2'-Bithiophen]-5-ylboronic acid;(5-thiophen-2-ylthiophen-2-yl)boronic Acid;2,2'-bithiophen-5-ylboronic acid;5-Borono-2,2'-bithiophene;C8H7BO2S2;Boronic acid,B-[2,2'-bithiophen]-5-yl-;5-(thiophen-2-yl)thiophen-2-ylboronic acid;AKOS BRN-0463;SCHEMBL288467;DTXSID90380065;PPHSULIZZOEBDD-UHFFFAOYSA-N;2,2'-Bithiophene-5-ylboronic acid;MFCD03086112;AKOS004119251;(2,2'-bithiophen)-5-yl-boronic acid;AB13111;{[2,2'-bithiophen]-5-yl}boronic acid;BS-20675;2,2/'-BITHIOPHENE-5-BORONIC ACID;CS-0173966;FT-0609195;2,2'-bithiophene-5-boronic acid, AldrichCPR;A806521;3-(3-AMINO-4-HYDROXY-PHENYL)-PROPIONICACID;BORONIC ACID, B-[2,2'-BITHIOPHEN]-5-YL-;J-006246

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

Chemical Property:

• Melting Point: 163-165℃
• Boiling Point: 416.1 °C at 760 mmHg
• Flash Point: 205.5 °C
• PSA: 96.94000
• Density: 1.42 g/cm³
• LogP: 1.15640
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 209.9980520
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,2''-Bithiophene-5-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(S1)C2=CC=CS2)(O)O

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

There total 6 articles about 2,2'-Bithiophene-5-boronic acid 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%

Trimethyl borate (121-43-7,63156-11-6) + 2,2'-Bithiophene (492-97-7) → 2,2'-bithiophene-5-boronic acid (132898-95-4)

Guidance literature:

2,2'-Bithiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; hexane; water;

Reference yield: 97.0%

5-bromo(2,2'-bithiophene) (3480-11-3) → 2,2'-bithiophene-5-boronic acid (132898-95-4)

Guidance literature:

5-bromo(2,2'-bithiophene); With magnesium; In tetrahydrofuran; at 20 ℃;

With Trimethyl borate; In tetrahydrofuran; at -65 ℃; for 1h; Further stages.;

DOI:10.1002/jhet.5570440417

Reference yield: 81.0%

triethyl borate (150-46-9) + 2,2'-Bithiophene (492-97-7) → 2,2'-bithiophene-5-boronic acid (132898-95-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; bithiophene and n-BuLi in hexane mixed in THF at 0°C under N2; B(OEt)2 added dropwise at -70°C; temp. raised to room temp.,stirredand aq. H2SO4 added; extn. with dichloromethane was done before aq. NaO H was added; to aq. layer added aq. HCl and compd. extd. with dichloromethane;

DOI:10.1021/jp075259j

upstream raw materials:

2,2'-Bithiophene

5-bromo(2,2'-bithiophene)

Trimethyl borate

triethyl borate

Downstream raw materials:

C₅₇H₃₆S₈

5-(4-bromophenyl)-[2,2']bithiophene

5'-[4-(3,6-bis{4-[2-(4-diphenylamino-phenyl)vinyl]phenyl}carbazol-9-yl)phenyl]-[2,2']bithiophenyl-5-carbaldehyde

N,N-diphenyl-4-(5-(thiophen-2-yl)thiophen-2-yl)benzenamine

Refernces

• 1、 An, Peng,Yu, Zhipeng,Lin, Qing. "Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells". . p. 9920 - 9922. Retrieved 2013.
• 2、 Dechant, Moritz,Fujii, Akihiko,Lehmann, Matthias,Ozaki, Masanori,Uzurano, Genya. "The liquid crystal Click procedure for oligothiophene-Tethered phthalocyanines-self-Assembly, alignment and photocurrent". . p. 5689 - 5698. Retrieved 2021/05/17.