Benzo[b]thiophene-2-carbonitrile

Base Information

• Chemical Name: Benzo[b]thiophene-2-carbonitrile
• CAS No.: 55219-11-9
• Molecular Formula: C9H5 N S
• Molecular Weight: 159.211
• Hs Code.: 2934999090
• European Community (EC) Number: 623-490-3
• DSSTox Substance ID: DTXSID3073555
• Nikkaji Number: J443.937F
• Wikidata: Q72440018
• ChEMBL ID: CHEMBL596116
• Mol file: 55219-11-9.mol

Synonyms:benzo[b]thiophene-2-carbonitrile;55219-11-9;Benzothiophene-2-carbonitrile;2-Cyanobenzothiophene;1-benzothiophene-2-carbonitrile;Benzo(b)thiophene-2-carbonitrile;SCHEMBL120641;CHEMBL596116;DTXSID3073555;MFCD09751294;AKOS012323503;CS-W022576;FS-2945;Benzo[b]thiophene-2-carbonitrile, 97%;FT-0646320;J-519709

Chemical Property of Benzo[b]thiophene-2-carbonitrile

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 24-28 °C
• Boiling Point: 140 °C/0.5 mmHg
• Flash Point: 110 °C
• PSA: 52.03000
• Density: 1.28g/cm³
• LogP: 2.77298
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 159.01427034
• Heavy Atom Count: 11
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Benzo[b]thiophene-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(S2)C#N
• Uses: Useful starter in benzothiophene chemistry.

Technology Process of Benzo[b]thiophene-2-carbonitrile

There total 8 articles about Benzo[b]thiophene-2-carbonitrile 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: 42.0%

Benzo[b]thiophene (95-15-8,11095-43-5) + (3,5-bis(trifluoromethyl)phenyl)(cyano)-l3-iodanyl trifluoromethanesulfonate → benzo[b]thiophene-3-carbonitrile (24434-84-2) + 2-cyanobenzothiophene (55219-11-9)

Guidance literature:

With iron(II) acetate; In 1,2-dichloro-ethane; at 70 ℃; for 48h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201309791

Reference yield: 2.0%

sodium cyanide (143-33-9,25596-52-5) + Benzo[b]thiophene (95-15-8,11095-43-5) → benzo[b]thiophene-3-carbonitrile (24434-84-2) + 2-cyanobenzothiophene (55219-11-9)

Guidance literature:

In methanol; for 46h; Ambient temperature; Pt foil electrode, 0.1 A constant current;

Reference yield:

benzothiophene-2-carboxaldehyde (3541-37-5) + 2-methoxy-phenylamine (90-04-0) → salicylonitrile (611-20-1) + 2-(benzo[b]thiophen-2-yl)benzo[d]oxazole (524945-67-3) + 2-cyanobenzothiophene (55219-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 72 h / 110 °C

2: 1 h / 700 °C / 0.01 Torr / flash vacuum pyrolysis

In toluene;

DOI:10.1002/jccs.201190029

upstream raw materials:

1,2-dithiophenyl-1,2-dicyanocyclopropane

sodium cyanide

Benzo[b]thiophene

benzo[b]thiophene-2-carboxamide

Downstream raw materials:

C₁₇H₁₃NOS

2-[1-(tert-butoxycarbonyl)-4-piperidinylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide

2-(1-Benzylpiperidin-4-ylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide

2-[1-(Ethoxycarbonyl)piperidin-4-ylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide

Refernces

• 1、 Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo. "Practical one-pot transformation of electron-rich aromatics into aromatic nitriles with molecular iodine and aq NH3 using Vilsmeier-Haack reaction". experimental part. p. 4588 - 4595. Retrieved 2012/07/27.
• 2、 -. "Anthranilic acid derivatives as inhibitors of the cGMP-phosphodiesterase". . . Retrieved 2008/06/13.