Indoline-7-carbonitrile

Base Information

• Chemical Name: Indoline-7-carbonitrile
• CAS No.: 115661-82-0
• Molecular Formula: C9H8N2
• Molecular Weight: 144.176
• Hs Code.: 2933990090
• European Community (EC) Number: 879-314-2
• DSSTox Substance ID: DTXSID60400522
• Wikidata: Q72458394
• Mol file: 115661-82-0.mol

Synonyms:indoline-7-carbonitrile;115661-82-0;7-indolinecarbonitrile;7-CYANOINDOLINE;2,3-dihydro-1H-indole-7-carbonitrile;1H-Indole-7-carbonitrile, 2,3-dihydro-;7-CYANO-2,3-DIHYDROINDOLE;MFCD01830669;SCHEMBL1119880;AMY2867;DTXSID60400522;YABRSQUYXZGQBW-UHFFFAOYSA-N;BCP06545;CS-B0547;AKOS006279897;SB66240;1H-Indole-7-carbonitrile,2,3-dihydro-;DS-13163;FT-0685905;EN300-2485550;A847957;Q-102611;2,3-Dihydro-1H-indol-7-carbonitrile;7-Cyano-1H-indoline;2,3-Dihydro-1H-indole-7-carbonitrile;7-Cyano-2,3-dihydroindole;Indoline-7-carbonitrile

Chemical Property of Indoline-7-carbonitrile

Chemical Property:

• Vapor Pressure: 0.000836mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 305.2 °C at 760 mmHg
• PKA: 2.63±0.20(Predicted)
• Flash Point: 138.4 °C
• PSA: 35.82000
• Density: 1.18 g/cm³
• LogP: 1.66428
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.068748264
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

7-Cyanoindoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC2=C1C=CC=C2C#N
• Uses: 7-Cyanoindoline has been used as a reactant in the preparation of silodosin (S465000), an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

Technology Process of Indoline-7-carbonitrile

There total 2 articles about Indoline-7-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: 60.5%

1-indoline (496-15-1) + methanolic sodium methanolate + trichloroacetonitrile (545-06-2) → 7-cyanoindoline (115661-82-0)

Guidance literature:

With BCl₃; In methanol; hexane; pentan-1-ol; water; toluene;

Reference yield: 58.0%

1-indoline (496-15-1) + trichloroacetonitrile (545-06-2) → 7-cyanoindoline (115661-82-0)

Guidance literature:

With boron trichloride; potassium carbonate; In methanol; dichloromethane; toluene;

Reference yield: 91.0%

7-cyanoindoline (115661-82-0) + 3-chloropropyl benzoate (942-95-0) → 1-(benzoyloxypropyl)-7-cyanoindoline hydrochloride

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 100 ℃; for 10h;

upstream raw materials:

1-indoline

trichloroacetonitrile

Downstream raw materials:

2,3-dihydro-1H-indole-7-carboxylic acid

silodosin

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

Refernces

• 1、 -. "Process for the production of 7-acylindoles". . . Retrieved 2008/06/13.