Benzothiophene-3-boronic acid

Base Information

• Chemical Name: Benzothiophene-3-boronic acid
• CAS No.: 113893-08-6
• Molecular Formula: C8H7BO2S
• Molecular Weight: 178.019
• Hs Code.: 29349990
• European Community (EC) Number: 808-005-7
• DSSTox Substance ID: DTXSID30380004
• Nikkaji Number: J1.800.109H
• Wikidata: Q72440004
• ChEMBL ID: CHEMBL342173
• Mol file: 113893-08-6.mol

Synonyms:113893-08-6;Benzothiophene-3-boronic acid;1-benzothiophen-3-ylboronic acid;benzo[b]thiophen-3-ylboronic acid;Benzo[b]thien-3-ylboronic acid;Benzo[b]thiophene-3-boronic acid;Thianaphthene-3-boronic acid;(1-benzothiophen-3-yl)boronic acid;Boronic acid, benzo[b]thien-3-yl-;Benzothiophene-3- boronic acid;CHEMBL342173;benzo[b]thiophene3-boronic acid;MFCD01114669;Boronic acid, B-benzo[b]thien-3-yl-;Benzothiophen-3-ylboronic Acid;1-Benzothiophene-3-boronic acid;1-BENZOTHIEN-3-YLBORONIC ACID;SCHEMBL9024;benzo[b]thiophen-3-ylboronicacid;DTXSID30380004;QVANIYYVZZLQJP-UHFFFAOYSA-N;1-benzothiophen-3-yl-boronic acid;1-Benzothiophene-3-ylboronic acid;CS-D0898;STR07400;BDBM50067907;AKOS004116364;AB08320;AM81129;NCGC00092009-01;NCGC00092009-02;NCGC00092009-03;AC-33872;SY038283;B4774;Benzo[b]thien-3-ylboronic acid, >=95.0%;FT-0622693;A22966;EN300-212528;J-003038;J-519701;Z1255383526;Benzo[b]thiophene-3-boronic Acid (contains varying amounts of Anhydride)

Chemical Property of Benzothiophene-3-boronic acid

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 8.67E-07mmHg at 25°C
• Melting Point: 225-230 °C(lit.)
• Refractive Index: 1.668
• Boiling Point: 390.207 °C at 760 mmHg
• PKA: 8.29±0.30(Predicted)
• Flash Point: 189.791 °C
• PSA: 68.70000
• Density: 1.355 g/cm³
• LogP: 0.58110
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 178.0259808
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

98% ^*data from raw suppliers

Benzo[b]thiophene-3-boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CSC2=CC=CC=C12)(O)O
• Uses: Benzo[b]thien-3-ylboronic acid can be used:To prepare thienyl substituted?pyrimidine derivatives as potent antimycobacterial?compounds.To prepare 3-O-protected 17-heteroaryl-3-hydroxyestra-1,3,5,16-tetraene-16-carbaldehyde, which in turn is used for the synthesis of heteroarenes-annelated estranes.As a substrate in the study of metal-free coupling reactions of allylic alcohols with heteroaryl boronic acids.As a starting material for the preparation of thienyl based quinoline and pyridine ligands, which are further used to synthesize platinum complexes.

Technology Process of Benzothiophene-3-boronic acid

There total 6 articles about Benzothiophene-3-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: 83.0%

3-Bromothianaphthene (7342-82-7) + Triisopropyl borate (5419-55-6) → benzo[b]thiophen-3-yl-3-boronic acid (113893-08-6)

Guidance literature:

3-Bromothianaphthene; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; for 1h; Inert atmosphere;

Reference yield: 59.0%

3-Bromothianaphthene (7342-82-7) + Trimethyl borate (121-43-7,63156-11-6) → benzo[b]thiophen-3-yl-3-boronic acid (113893-08-6)

Guidance literature:

3-Bromothianaphthene; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.11.010

Reference yield:

3-Bromothianaphthene (7342-82-7) + isopropoxyboronic acid (52732-22-6) → benzo[b]thiophen-3-yl-3-boronic acid (113893-08-6)

Guidance literature:

With n-butyllithium; at -78 ℃; for 24h; Inert atmosphere;

upstream raw materials:

3-Bromothianaphthene

Triisopropyl borate

Trimethyl borate

isopropoxyboronic acid

Downstream raw materials:

2-(1-benzothiophen-3-yl)-4,6-dichloro-5-phenylpyrimidine

C₅₈H₅₆N₆O₄S

5-(benzo[b]thiophen-3-yl)-2-hydroxy-3-methoxybenzaldehyde

Refernces

• 1、 -. "1,8-dialkyl-1,4,5,8-naphthalimide compound and preparation method thereof". Paragraph 0033-0035; 0051-0053; 0069-0071. . Retrieved 2020/06/02.
• 2、 -. "NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE". Paragraph 0162; 0163. . Retrieved 2013/07/31.