4,4'-Pentamethylenedioxydibenzonitrile

Base Information

• Chemical Name: 4,4'-Pentamethylenedioxydibenzonitrile
• CAS No.: 7467-71-2
• Molecular Formula: C19H18 N2 O2
• Molecular Weight: 306.364
• European Community (EC) Number: 231-263-1
• NSC Number: 400559
• DSSTox Substance ID: DTXSID90225649
• Nikkaji Number: J278.874H
• Wikidata: Q83104707
• Mol file: 7467-71-2.mol

Synonyms:4,4'-Pentamethylenedioxydibenzonitrile;7467-71-2;4-[5-(4-cyanophenoxy)pentoxy]benzonitrile;Benzonitrile, 4,4'-[1,5-pentanediylbis(oxy)]bis-;EINECS 231-263-1;4,4'-(PENTANE-1,5-DIYLBIS(OXY))DIBENZONITRILE;Benzonitrile, 4,4'-(1,5-pentanediylbis(oxy))bis-;NSC400559;SCHEMBL5526919;1,5-bis(4-cyanophenoxy)pentane;DTXSID90225649;4,4'-Dicyano-1,5-diphenoxypentane;NSC 400559;NSC-400559;4,4'-(1,5-Pentanediylbisoxy)bisbenzonitrile;C13781;4-([5-(4-Cyanophenoxy)pentyl]oxy)benzonitrile #;4-{[5-(4-CYANOPHENOXY)PENTYL]OXY}BENZONITRILE

Chemical Property of 4,4'-Pentamethylenedioxydibenzonitrile

Chemical Property:

• Boiling Point: 515.4°Cat760mmHg
• Flash Point: 199.7°C
• Density: 1.16g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 306.136827821
• Heavy Atom Count: 23
• Complexity: 377

Purity/Quality:

99%+, ^*data from raw suppliers

4,4'-PENTAMETHYLENEDIOXYDIBENZONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)OCCCCCOC2=CC=C(C=C2)C#N

Technology Process of 4,4'-Pentamethylenedioxydibenzonitrile

There total 4 articles about 4,4'-Pentamethylenedioxydibenzonitrile 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: 95.7%

1,5-dibromo-pentane (111-24-0) + 4-cyanophenol (767-00-0) → 4,4′-(pentane-1,5-diylbis(oxy))dibenzonitrile (7467-71-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 80 ℃; for 1h;

DOI:10.1007/s11171-005-0047-z

Reference yield:

4-cyanophenyl acetate (13031-41-9) → 4,4′-(pentane-1,5-diylbis(oxy))dibenzonitrile (7467-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 4percent KOH / ethanol / 0.33 h / Heating

2: 1.) aq. NaOH / 1.) C₂H₅OH, reflux, 1 h, 2.) C₂H₅OH, reflux, 3 h

With potassium hydroxide; sodium hydroxide; In ethanol;

Reference yield:

4-hydroxybenzaldehyde oxime (699-06-9,60221-52-5,60221-53-6) → 4,4′-(pentane-1,5-diylbis(oxy))dibenzonitrile (7467-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 1 h / Heating

2: 88 percent / 4percent KOH / ethanol / 0.33 h / Heating

3: 1.) aq. NaOH / 1.) C₂H₅OH, reflux, 1 h, 2.) C₂H₅OH, reflux, 3 h

With potassium hydroxide; sodium hydroxide; In ethanol;

upstream raw materials:

1,5-dibromo-pentane

sodium 4-cyanophenolate

4-cyanophenol

4-cyanophenyl acetate

Downstream raw materials:

1,5-Bis-<4-ethoxythiocarbonyl-phenoxy>-pentan

1,5-bis(4-acetoxyamidinophenoxy)pentane (diacetyldiamidoxime ester)

Pentamidine hydrochloride

1,5-bis[4-(1H-tetrazol-5-yl)phenoxy]pentane

Refernces

• 1、 Siboni, Ruth B.,Bodner, Micah J.,Khalifa, Muhammad M.,Docter, Aaron G.,Choi, Jessica Y.,Nakamori, Masayuki,Haley, Michael M.,Berglund, J. Andrew. "Biological Efficacy and Toxicity of Diamidines in Myotonic Dystrophy Type 1 Models". . p. 5770 - 5780. Retrieved 2015/08/24.
• 2、 Bakunova, Svetlana M.,Bakunov, Stanislav A.,Patrick, Donald A.,Kumar, E. V. K. Suresh,Ohemeng, Kwasi A.,Bridges, Arlene S.,Wenzler, Tanja,Barszcz, Todd,Jones, Susan Kilgore,Werbovetz, Karl A.,Brun, Reto,Tidwell, Richard R.. "Structure-activity study of pentamidine analogues as antiprotozoal agents". scheme or table. p. 2016 - 2035. Retrieved 2009/12/31.