(E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile

Base Information

• Chemical Name: (E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile
• CAS No.: 221530-44-5
• Molecular Formula: C13H11 N O
• Molecular Weight: 197.236
• European Community (EC) Number: 816-027-3
• DSSTox Substance ID: DTXSID10474076
• Nikkaji Number: J1.908.425F,J3.085.853K
• Wikidata: Q72505823
• Mol file: 221530-44-5.mol

Synonyms:196597-79-2;(E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile;221530-44-5;(1,2,6,7,-Tetrahydro-8H-Indeno[5,4-B]Furan-8-Ylidene)Acetonitrile;(2E)-2-(1,2,6,7-tetrahydrocyclopenta[e][1]benzofuran-8-ylidene)acetonitrile;2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile;Acetonitrile, (1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-, (2E)-;Acetonitrile, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-, (2E)-;(E)-2-(1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile;starbld0009326;SCHEMBL339504;DTXSID10474076;TUFWVKLKUFXARX-BJMVGYQFSA-N;CS-M2278;AKOS006314749;CS-14592;A880086;(2E)-(1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile;(E)-(1,6,7,8-Tetrahydro-2H-indeno[5,4- b]furan-8-ylidene)acetonitrile;(E)-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]-furan-8-ylidene)acetonitrile;(E)-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile;Acetonitrile,2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-;2-[(8E)-1H,2H,6H,7H,8H-INDENO[5,4-B]FURAN-8-YLIDENE]ACETONITRILE

Chemical Property of (E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 149-1510C
• Refractive Index: 1.711
• Boiling Point: 392.132°C at 760 mmHg
• Flash Point: 164.971°C
• PSA: 33.02000
• Density: 1.321g/cm³
• LogP: 2.47468
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 197.084063974
• Heavy Atom Count: 15
• Complexity: 338

Purity/Quality:

99% ^*data from raw suppliers

(1,2,6,7,-Tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=CC#N)C2=C1C=CC3=C2CCO3
• Isomeric SMILES: C1C/C(=C\C#N)/C2=C1C=CC3=C2CCO3
• Uses: An indenofuran as intermediate for pharmaceuticals for treatment of sleep disorder Ramelteon Ramelteon intermediate. An indenofuran as intermediate for pharmaceuticals for treatment of sleep disorder.

Technology Process of (E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile

There total 2 articles about (E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile 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:

(8-hydroxy-4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)acetonitrile → 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile (221530-44-5) + 2,2'-bis(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)diethylamine + 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)?1?ethylamine (448964-37-2,196597-81-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; acetic acid; at 60 ℃; for 18h; under 22502.3 Torr;

DOI:10.1021/op500386g

Reference yield:

4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (196597-77-0) → 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile (221530-44-5) + 2,2'-bis(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)diethylamine + 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)?1?ethylamine (448964-37-2,196597-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C / Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / methanol; acetic acid / 18 h / 60 °C / 22502.3 Torr

With n-butyllithium; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; hexane; acetic acid;

DOI:10.1021/op500386g

Reference yield: 97.0%

2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile (221530-44-5) → 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)ethylamine hydrochloride (1053239-39-6)

Guidance literature:

With hydrogen; platinum(IV) chloride; In methanol; chloroform; at 30 - 40 ℃; for 2h; under 2250.23 - 3750.38 Torr; Solvent; Reagent/catalyst;

upstream raw materials:

4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Downstream raw materials:

2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)?1?ethylamine

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetonitrile

C₁₃H₁₅NO

N-(2-[7-(2-methoxyphenyl)-1,6-dihydro-2H-indeno[5,4-b]-furan-8-yl]ethyl)acetamide