(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.: 196597-79-2
• Molecular Formula: C13H11NO
• Molecular Weight: 197.236
• Hs Code.: 2932999099
• European Community (EC) Number: 816-027-3
• DSSTox Substance ID: DTXSID10474076
• Nikkaji Number: J1.908.425F,J3.085.853K
• Wikidata: Q72505823
• Mol file: 196597-79-2.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:

• Melting Point: 146-151℃
• Boiling Point: 392.132 °C at 760 mmHg
• Flash Point: 164.971 °C
• PSA: 33.02000
• Density: 1.321 g/cm³
• LogP: 2.47468
• Storage Temp.: 2-8°C
• 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:

99.5% ^*data from raw suppliers

(E)-2-(6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(=CC#N)C2=C1C=CC3=C2CCO3
• Isomeric SMILES: C1C/C(=C\C#N)/C2=C1C=CC3=C2CCO3

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

There total 11 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: 88.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one (196597-78-1) → (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile (196597-79-2)

Guidance literature:

With sodium methylate; In methanol; water; toluene;

Reference yield:

2.3-dihydrobenzofuran (496-16-2) → (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile (196597-79-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 92 percent / TiCl₄ / CH₂Cl₂ / 1 h

2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

2.2: 88 percent / tetrahydrofuran / 1 h / 20 °C

3.1: 99 percent / H₂ / 10percent Pd/C/H₂O / ethanol / 2 h / 20 °C

4.1: 97 percent / NaOAc; AcOH; Br₂ / 1 h / 20 °C

5.1: 53 percent / AcOH; Fe; Br₂ / 5 h / 50 °C

6.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C

7.1: SOCl₂ / 75 °C

8.1: AlCl₃ / 1,2-dichloro-ethane / 20 °C

9.1: 89 percent / AcOH; H₂ / 10percent Pd/C/H₂O / 1 h / 20 °C

10.1: NaH / tetrahydrofuran / 20 °C

10.2: 60 percent / tetrahydrofuran / 20 °C

With potassium hydroxide; aluminium trichloride; thionyl chloride; hydrogen; bromine; sodium acetate; titanium tetrachloride; iron; sodium hydride; acetic acid; 10percent Pd/C/H₂O; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; 1.1: Vilsmeier-Haack reaction / 2.2: Horner-Emmons reaction / 8.1: Friedel-Crafts cyclization / 10.2: Horner-Emmons reaction;

DOI:10.1021/jm0201159

Reference yield:

2,3-dihydro-benzofuran-5-carbaldehyde (55745-70-5) → (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile (196597-79-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C

2.1: 99 percent / H₂ / 10percent Pd/C/H₂O / ethanol / 2 h / 20 °C

3.1: 97 percent / NaOAc; AcOH; Br₂ / 1 h / 20 °C

4.1: 53 percent / AcOH; Fe; Br₂ / 5 h / 50 °C

5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C

6.1: SOCl₂ / 75 °C

7.1: AlCl₃ / 1,2-dichloro-ethane / 20 °C

8.1: 89 percent / AcOH; H₂ / 10percent Pd/C/H₂O / 1 h / 20 °C

9.1: NaH / tetrahydrofuran / 20 °C

9.2: 60 percent / tetrahydrofuran / 20 °C

With potassium hydroxide; aluminium trichloride; thionyl chloride; hydrogen; bromine; sodium acetate; iron; sodium hydride; acetic acid; 10percent Pd/C/H₂O; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; 1.2: Horner-Emmons reaction / 7.1: Friedel-Crafts cyclization / 9.2: Horner-Emmons reaction;

DOI:10.1021/jm0201159

upstream raw materials:

diethyl 1-cyanomethylphosphonate

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

2.3-dihydrobenzofuran

2,3-dihydro-benzofuran-5-carbaldehyde

Downstream raw materials:

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

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

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

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

Refernces

• 1、 -. "Pharmaceutical preparation containing copolyvidone". Page/Page column 40. . Retrieved 2018/11/06.
• 2、 -. "PROCESS FOR PREPARATION OF (S)-N-[2-(1,6,7,8-TETRAHYDRO-2H-INDENO[5,4-B]FURAN-8-YL)ETHYL] PROPIONAMIDE AND NOVEL INTERMEDIATES THEREOF". Page/Page column 24 ;30. . Retrieved 2010/04/28.