(6-Cyanobenzo[b]thiophen-2-yl)boronic acid

Base Information

• Chemical Name: (6-Cyanobenzo[b]thiophen-2-yl)boronic acid
• CAS No.: 1119899-35-2
• Molecular Formula: C9H6BNO2S
• Molecular Weight: 203.029
• DSSTox Substance ID: DTXSID80705147
• Wikidata: Q82637877
• Mol file: 1119899-35-2.mol

Synonyms:(6-Cyanobenzo[b]thiophen-2-yl)boronic acid;1119899-35-2;(6-cyano-1-benzothiophen-2-yl)boronic acid;6-cyanobenzo[b]thiophen-2-ylboronic acid;SCHEMBL1612576;DTXSID80705147;CS-0441206;A894668

Chemical Property of (6-Cyanobenzo[b]thiophen-2-yl)boronic acid

Chemical Property:

• Boiling Point: 474.9±48.0 °C(Predicted)
• PKA: 6.32±0.30(Predicted)
• PSA: 92.49000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 0.45278
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 203.0212298
• Heavy Atom Count: 14
• Complexity: 265

Purity/Quality:

98%min ^*data from raw suppliers

(6-Cyanobenzo[b]thiophen-2-yl)boronicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(S1)C=C(C=C2)C#N)(O)O

Technology Process of (6-Cyanobenzo[b]thiophen-2-yl)boronic acid

There total 1 articles about (6-Cyanobenzo[b]thiophen-2-yl)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: 72.0%

benzo[b]thiophene-6-carbonitrile (154650-81-4) → 6-cyanobenzo[b]thiophen-2-ylboronic acid (1119899-35-2)

Guidance literature:

benzo[b]thiophene-6-carbonitrile; With n-butyllithium; In tetrahydrofuran; hexanes; at -90 ℃; for 0.5h;

With Trimethyl borate; In tetrahydrofuran; hexanes; at -90 ℃; for 0.5h;

With hydrogenchloride; water; In tetrahydrofuran; hexanes; at -90 - 30 ℃; for 0.5h;

Reference yield: 90.0%

6-cyanobenzo[b]thiophen-2-ylboronic acid (1119899-35-2) + 4-bromobenzenecarbonitrile (623-00-7) → 2-(4-cyanophenyl)benzo[b]thiophene-6-carbonitrile (27047-25-2)

Guidance literature:

With palladium diacetate; potassium carbonate; johnphos; In N,N-dimethyl-formamide; at 100 ℃; for 4h; Inert atmosphere; Sealed tube;

DOI:10.1021/jm901852f

Reference yield: 47.0%

6-cyanobenzo[b]thiophen-2-ylboronic acid (1119899-35-2) + (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine (1142947-81-6) → 2-(2-(3-(4-methylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzo[b]thiophene-6-carbonitrile (1142947-47-4)

Guidance literature:

With sodium carbonate; CyJohnPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; N,N-dimethyl-formamide; at 160 ℃; for 0.75h; Microwave irradiation;

upstream raw materials:

benzo[b]thiophene-6-carbonitrile

Downstream raw materials:

2-(2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)-5-methylpyrimidin-4-yl)benzo[b]thiophene-6-carbonitrile

2-(2-(4-(4-methylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzo[b]thiophene-6-carbonitrile

2-{2-[4-(2-methyl-imidazol-1-ylmethyl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-benzo[b]thiophene-6-carbonitrile

2-(2-(3-(4-methylpiperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzo[b]thiophene-6-carbonitrile

Refernces

• 1、 -. "PYRROLOPYRIMIDINE COMPOUNDS AND THEIR USE AS JANUS KINASE MODULATORS". Page/Page column 89. . Retrieved 2009/05/28.