3-Thiopheneboronic acid

Base Information

• Chemical Name: 3-Thiopheneboronic acid
• CAS No.: 6165-69-1
• Molecular Formula: C4H5BO2S
• Molecular Weight: 127.959
• Hs Code.: 29339900
• European Community (EC) Number: 629-166-8
• DSSTox Substance ID: DTXSID60342433
• Nikkaji Number: J478.720J
• Wikidata: Q72508793
• ChEMBL ID: CHEMBL341722
• Mol file: 6165-69-1.mol

Synonyms:thiophene-3-boronic acid

Chemical Property of 3-Thiopheneboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 164-169 °C(lit.)
• Boiling Point: 287.9 °C at 760 mmHg
• PKA: 8.25±0.10(Predicted)
• Flash Point: 127.9 °C
• PSA: 68.70000
• Density: 1.32 g/cm³
• LogP: -0.57210
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 128.0103307
• Heavy Atom Count: 8
• Complexity: 78.4

Purity/Quality:

99% ^*data from raw suppliers

Thiophene-3-boronic acid 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CSC=C1)(O)O
• Uses: suzuki reaction 3-Thiopheneboronic Acid is used in the synthesis of porphyrins as inhibitiors of telomerase. It is also used to prepare 1,4-disubstituted imidazoles as potential antibacterial agents.

Technology Process of 3-Thiopheneboronic acid

There total 14 articles about 3-Thiopheneboronic 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: 96.0%

water (7732-18-5) + potassium 3-thiophenetrifluoroborate → Thien-3-ylboronic acid (6165-69-1)

Guidance literature:

With montmorillonite K₁₀; at 25 ℃; for 0.75h;

DOI:10.21577/0103-5053.20180126

Reference yield: 91.0%

3-Bromothiophene (872-31-1) → Thien-3-ylboronic acid (6165-69-1)

Guidance literature:

3-Bromothiophene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -50 ℃;

With Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -50 - -15 ℃;

With sodium hydroxide; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/jm049696n

Reference yield: 91.0%

→ Thien-3-ylboronic acid (6165-69-1)

Guidance literature:

upstream raw materials:

3-thienyl lithium

diethyl ether

boric acid tributyl ester

3-Bromothiophene

Downstream raw materials:

3-(3'-Thienyl)-2-cyclohexen-1-one

(2S,4R)-2-Butyl-4-[2-(4-thiophen-3-yl-phenyl)-ethyl]-pentanedioic acid 1-tert-butyl ester 5-(2-trimethylsilanyl-ethyl) ester

5-[(3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-7-(3-nitro-benzyl)-6-oxo-hexahydro-1,3-dioxa-5,7-diaza-azulen-5-ylmethyl]-3-thiophen-3-yl-indazole-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Honda, Mitsunori,Taniguchi, Yusuke,Hayashi, Tomohiro,Kunimoto, Ko-Ki,Segi, Masahito,Yamaguchi, Takahiro. "Synthesis and utility of 3-silylthiophenes having perfluoroalkyl groups". . p. 4554 - 4558. Retrieved 2017.
• 2、 Silva, Renato L.,Santos, Cosme S.,Santos, Jonh A. M.,Oliveira, Roberta A.,Menezes, Paulo H.,Freitas, Juliano C. R.. "An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10". . p. 1777 - 1785. Retrieved 2018/09/04.