2-(But-3-en-1-yl)benzonitrile

Base Information

• Chemical Name: 2-(But-3-en-1-yl)benzonitrile
• CAS No.: 62170-45-0
• Molecular Formula: C11H11N
• Molecular Weight: 157.215
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID20559585
• Nikkaji Number: J1.207.362C
• Wikidata: Q82442343
• Mol file: 62170-45-0.mol

Synonyms:2-(But-3-en-1-yl)benzonitrile;62170-45-0;4-(2-Cyanophenyl)-1-butene;2-but-3-enylbenzonitrile;MFCD01319564;SCHEMBL16115312;DTXSID20559585;COEKIOUOIHGYEJ-UHFFFAOYSA-N;AKOS016016750

Chemical Property of 2-(But-3-en-1-yl)benzonitrile

Chemical Property:

• Vapor Pressure: 0.0316mmHg at 25°C
• Boiling Point: 243.7oC at 760 mmHg
• Flash Point: 101.1oC
• PSA: 23.79000
• Density: 0.97g/cm3
• LogP: 2.67688
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 157.089149355
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

97% ^*data from raw suppliers

4-(2-Cyanophenyl)-1-butene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCCC1=CC=CC=C1C#N

Technology Process of 2-(But-3-en-1-yl)benzonitrile

There total 10 articles about 2-(But-3-en-1-yl)benzonitrile 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: 97.0%

C16H23NO2Si (119204-70-5) → 2-(but-3-en-1-yl)benzonitrile (62170-45-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 5h; Heating;

DOI:10.1016/S0040-4020(01)81693-8

Reference yield: 86.0%

2-Methylbenzonitrile (529-19-1) + allyl bromide (106-95-6) → 2-(but-3-en-1-yl)benzonitrile (62170-45-0)

Guidance literature:

2-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: 72.0%

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + 2-cyanobenzyl chloride (612-13-5) → 2-(but-3-en-1-yl)benzonitrile (62170-45-0)

Guidance literature:

With palladium diacetate; cesium fluoride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; at 80 ℃; for 12h; Inert atmosphere;

upstream raw materials:

C₁₆H₂₃NO₂Si

C₁₆H₂₃NO₂Si

2-Methylbenzonitrile

allyl bromide

Downstream raw materials:

(2-(but-3-en-1-yl)phenyl)methanamine

Refernces

• 1、 Panteleeva,Kondrat'Ev,Goryunov,Koval',Luk'Yanets,Shteingarts. "Synthesis of phthalonitriles containing ω-alkenyl, ω-(alkylsulfanyl)alkyl, and ω-(alkylsulfonyl)alkyl substituents and phthalocyanine derivatives based thereon". . p. 138 - 144. Retrieved 2013/04/10.
• 2、 Panteleeva,Vaganova,Luk'yanets,Shteingarts. "Reductive activation of arenes: XIX. Mechanism and some synthetic applications of the alkylation of phthalodinitrile radical anion". . p. 1280 - 1288. Retrieved 2007/10/03.