3-Hexenedinitrile

Base Information

• Chemical Name: 3-Hexenedinitrile
• CAS No.: 18715-38-3
• Molecular Formula: C6H6 N2
• Molecular Weight: 106.127
• European Community (EC) Number: 214-287-7,242-519-7
• UNII: FMI3J48MFI
• DSSTox Substance ID: DTXSID201314365
• Nikkaji Number: J151.259E,J27.804A
• Mol file: 18715-38-3.mol

Synonyms:1,4-Dicyano-2-butene;1119-85-3;3-HEXENEDINITRILE;(E)-Hex-3-enedinitrile;18715-38-3;trans-3-Hexenedinitrile;beta-Hydromucononitrile;(3E)-hex-3-enedinitrile;3-Hexenedinitrile, (3E)-;trans-1,4-Dicyano-2-butene;HSDB 5790;(E)-3-Hexenedinitrile;(3E)-3-Hexenedinitrile;EINECS 214-287-7;UNII-FMI3J48MFI;UNII-W0IHU4R7XO;NSC 11685;FMI3J48MFI;BRN 1720228;EINECS 242-519-7;4-02-00-02238 (Beilstein Handbook Reference);.beta.-Hydromucononitrile;1,4-dicyano-trans-2-butene;Dihydromucononitrile;1,4-Dicyano butene-2;W0IHU4R7XO;3-Hexenedinitrile, (E)-;(3E)-3-Hexenedinitrile #;1,4-Dicyano-2-butene,trans;SCHEMBL818468;SCHEMBL819793;trans-3-Hexenedinitrile, 97%;BSVZXPLUMFUWHW-OWOJBTEDSA-N;DTXSID201314365;BAA11985;MFCD00001964;AKOS015913693;TRANS-.BETA.-HYDROMUCONONITRILE;AS-57327;LS-75550;CS-0374361;H0357;D78348;EN300-1705948;J-002681;Q27278075;InChI=1/C6H6N2/c7-5-3-1-2-4-6-8/h1-2H,3-4H2/b2-1

Chemical Property of 3-Hexenedinitrile

Chemical Property:

• Boiling Point: 289.6°Cat760mmHg
• Flash Point: 146.2°C
• PSA: 47.58000
• Density: 0.983g/cm³
• LogP: 1.36996
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 106.053098200
• Heavy Atom Count: 8
• Complexity: 142

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-3-Hexenedinitrile 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(C=CCC#N)C#N
• Isomeric SMILES: C(/C=C/CC#N)C#N

Technology Process of 3-Hexenedinitrile

There total 15 articles about 3-Hexenedinitrile 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: 99.0%

→ trans-1,4-dicyano-2-butene (18715-38-3)

Guidance literature:

Reference yield: 80.0%

(E)-1,2-dibromoethene (590-12-5) + 2-trimethylsilylacetonitrile (18293-53-3) → trans-1,4-dicyano-2-butene (18715-38-3)

Guidance literature:

With copper(l) iodide; In acetonitrile; for 20h; Reflux;

Reference yield:

acrylonitrile (107-13-1,25014-41-9) → trans-1,4-dicyano-2-butene (18715-38-3) + cis-1,4-dicyanobut-1-ene (2141-58-4) + trans-1,4-dicyanobut-1-ene (2141-59-5) + 2,4-dicyano-1-butene (1572-52-7)

Guidance literature:

isopropyl diphenylphosphinite; In isopropyl alcohol; toluene; at 60 ℃; Further Variations:; Catalysts; Solvents; Temperatures; Kinetics;

DOI:10.1039/a707559f

upstream raw materials:

1,4-dichloro-2-butene

sodium cyanide

hydrogen cyanide

trans-1,4-dichlorobut-2-ene

Downstream raw materials:

Diethyl trans-hex-3-enedioate

(E)-2,5-bis((Z)-4-(dimethylamino)benzylidene)hex-3-enedinitrile

N-((1E,5E)-4,7-dicyano-1-phenylhepta-1,5-dien-3-yl)-4-methylbenzenesulfonamide

(E)-N-(2,5-dicyano-1-phenylpent-3-enyl)-4-methylbenzenesulfonamide

Refernces

• 1、 -. "Preparation method 1,4-cyano -2-butene". Paragraph 0017; 0020; 0022; 0025; 0026; 0029; 0030; 0034. . Retrieved 2020/04/17.
• 2、 Hall, C. Dennis,Lowther, Nicholas,Tweedy, Bruce R.,Hall, Adam C.,Shaw, Gordon. "The kinetics and mechanism of the phosphorus-catalysed dimerisation of acrylonitrile". . p. 2047 - 2054. Retrieved 2007/10/03.