4-(4-Cyanophenyl)-1-butene

Base Information

• Chemical Name: 4-(4-Cyanophenyl)-1-butene
• CAS No.: 15451-33-9
• Molecular Formula: C11H11N
• Molecular Weight: 157.215
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50471600
• Nikkaji Number: J1.207.366F
• Mol file: 15451-33-9.mol

Synonyms:15451-33-9;4-(4-CYANOPHENYL)-1-BUTENE;4-(3-butenyl)benzonitrile;4-but-3-enylbenzonitrile;MFCD01319571;Benzonitrile, 4-(3-butenyl)-;4-(3-butenyl)-benzonitrile;4-(but-3-en-1-yl)benzonitrile;SCHEMBL2968409;DTXSID50471600;WNIAOHACTUJSLN-UHFFFAOYSA-N;AKOS006280102;FT-0731030

Chemical Property of 4-(4-Cyanophenyl)-1-butene

Chemical Property:

• Vapor Pressure: 0.014mmHg at 25°C
• Boiling Point: 258.425oC at 760 mmHg
• Flash Point: 110.173oC
• PSA: 23.79000
• Density: 0.977g/cm3
• LogP: 2.67688
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 157.089149355
• Heavy Atom Count: 12
• Complexity: 178

Purity/Quality:

4-(4-cyanophenyl)-1-butene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCCC1=CC=C(C=C1)C#N

Technology Process of 4-(4-Cyanophenyl)-1-butene

There total 16 articles about 4-(4-Cyanophenyl)-1-butene 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: 86.0%

1-bromo-4-butene (5162-44-7) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(but-3-en-1-yl)benzonitrile (15451-33-9)

Guidance literature:

1-bromo-4-butene; With iodine; zinc; In N,N-dimethyl acetamide; at 80 ℃;

4-bromobenzenecarbonitrile; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl acetamide; at 20 ℃; Further stages.;

DOI:10.1021/ol0272693

Reference yield: 85.0%

para-methylbenzonitrile (104-85-8) + allyl bromide (106-95-6) → 4-(but-3-en-1-yl)benzonitrile (15451-33-9)

Guidance literature:

para-methylbenzonitrile; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

allyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1080/00304949909355729

Reference yield: 82.0%

4-(3-hydroxy-pent-4-ynyl)-benzonitrile → 4-(but-3-en-1-yl)benzonitrile (15451-33-9)

Guidance literature:

With lithium trifluoromethanesulfonate; In toluene; at 110 ℃; for 5h;

DOI:10.1021/ja036246w

upstream raw materials:

1-bromo-4-butene

4-bromobenzenecarbonitrile

allyl bromide

4-cyanobenzyl bromide

Downstream raw materials:

4-(but-3-en-1-yl)benzoic acid

1-(4-(but-3-en-1-yl)phenyl)ethan-1-one

4-(4-hydroxybutyl)benzonitrile

4-(3-buten-1-yl)benzoic acid methyl ester

Refernces

• 1、 Panteleeva, Elena V.,Vaganova, Tamara A.,Shteingarts, Vitalij D.,Bilkis, Isaak I.. "Evidence for the transition from SN to ET mechanism in the reaction of arene radical anion with alkyl halide evoked by the introduction of an electron withdrawing substituent into radical anion". . p. 8465 - 8466. Retrieved 1995.
• 2、 -. "Efficient preparation method of 1-aryl-4-butene compound". Paragraph 0063-0066; 0071-0074. . Retrieved 2020/05/30.
• 3、 Challinor, Amy J.,Calin, Marc,Nichol, Gary S.,Carter, Neil B.,Thomas, Stephen P.. "Amine-Activated Iron Catalysis: Air- and Moisture-Stable Alkene and Alkyne Hydrofunctionalization". supporting information. p. 2404 - 2409. Retrieved 2016/08/16.