(2Z)-3,7-dimethylocta-2,6-dienenitrile

Base Information

• Chemical Name: (2Z)-3,7-dimethylocta-2,6-dienenitrile
• CAS No.: 31983-27-4
• Molecular Formula: C10H15N
• Molecular Weight: 149.236
• Hs Code.: 2926909090
• European Community (EC) Number: 250-883-3
• UNII: H0A28Q5S6U
• DSSTox Substance ID: DTXSID0044816
• Nikkaji Number: J47.202F
• Wikidata: Q27279405
• Metabolomics Workbench ID: 130699
• ChEMBL ID: CHEMBL3188973
• Mol file: 31983-27-4.mol

Synonyms:31983-27-4;Neral nitrile;(2Z)-3,7-dimethylocta-2,6-dienenitrile;(Z)-3,7-DIMETHYL-2,6-OCTADIENENITRILE;2,6-Octadienenitrile, 3,7-dimethyl-, (2Z)-;UNII-H0A28Q5S6U;H0A28Q5S6U;DTXSID0044816;2,6-Octadienenitrile, 3,7-dimethyl-, (Z)-;EINECS 250-883-3;cis-3,7-Dimethyl-2,6-octadienenitrile;(Z)-3,7-Dimethylocta-2,6-dienenitrile;Neryl nitrile;cis-Geranylnitrile;(Z) - 3,7 - dimethylocta - 2,6 - dienenitrile;SCHEMBL1472323;CHEMBL3188973;DTXCID8024816;Tox21_301273;NCGC00256282-01;1-Boc-6-fluoro-1H-indole-2-boronicacid;CAS-31983-27-4;(3E)-4,7-Dimethyl-3,6-octadienenitrile #;Q27279405

Chemical Property of (2Z)-3,7-dimethylocta-2,6-dienenitrile

Chemical Property:

• Appearance/Colour: Colourless to pale yellow oily liquid
• Vapor Pressure: 0.025mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Boiling Point: 247.9 °C at 760 mmHg
• Flash Point: 103.7 °C
• PSA: 23.79000
• Density: 0.858 g/cm³
• LogP: 3.20268
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 149.120449483
• Heavy Atom Count: 11
• Complexity: 208

Purity/Quality:

99% ^*data from raw suppliers

(Z)-3,7-Dimethyl-2,6-octadienenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XnN
• Hazard Codes: Xn,N
• Statements: 51/53-68
• Safety Statements: 36/37-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CC#N)C)C
• Isomeric SMILES: CC(=CCC/C(=C\C#N)/C)C

Technology Process of (2Z)-3,7-dimethylocta-2,6-dienenitrile

There total 6 articles about (2Z)-3,7-dimethylocta-2,6-dienenitrile 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: 96.0%

citral dimethylhydrazone (334475-34-2) → N-methylmethyleneamine N-oxide (54125-41-6) + (Z)-3,7-dimethyl-2,6-octadiene nitrile (31983-27-4,80748-12-5)

Guidance literature:

With dihydrogen peroxide; methyltrioxorhenium(VII); In ethanol; at -50 - 20 ℃; for 1h;

DOI:10.1039/a804839h

Reference yield:

geranylamine (35278-77-4) → (Z)-3,7-dimethyl-2,6-octadiene nitrile (31983-27-4,80748-12-5) + (E)-3,7-dimethylocta-2,6-dienenitrile (5585-39-7,80748-12-5)

Guidance literature:

With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; at 20 ℃; for 15h; under 760.051 Torr; Reagent/catalyst; Overall yield = 95 %;

DOI:10.1021/cs400360e

Reference yield:

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) + cyanoacetic acid (372-09-8) → (Z)-3,7-dimethyl-2,6-octadiene nitrile (31983-27-4,80748-12-5) + (E)-3,7-dimethylocta-2,6-dienenitrile (5585-39-7,80748-12-5) + (Z)-3,7-dimethyl-3,6-octadiene nitrile (26509-72-8,26509-71-7) + 7-methyl-3-methylene-6-octene nitrile (26410-85-5) + (E)-3,7-dimethyl-3,6-octadiene nitrile (26509-72-8,26509-71-7)

Guidance literature:

With pyridine; 1,4-diaminobutane; In toluene; at 112 ℃; for 8h; Concentration; Pressure; Reagent/catalyst; Solvent; Temperature; Time; Overall yield = 80.8 %; Inert atmosphere;

upstream raw materials:

citral dimethylhydrazone

geraniol

geranylamine

6-Methyl-hept-5-en-2-on

Refernces

• 1、 Danahy, Kelley E.,Styduhar, Evan D.,Fodness, Aria M.,Heckman, Laurel M.,Jamison, Timothy F.. "On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine". supporting information. p. 8392 - 8395. Retrieved 2020/11/18.
• 2、 Shen, Yifan,Zhou, Yu,Jiang, Lili,Ding, Guangni,Luo, Luo,Zhang, Zhaoguo,Xie, Xiaomin. "Selective aerobic oxidation of benzylic amines to aryl nitriles catalyzed by CuBr2/N-methyl imidazole". . p. 4266 - 4271. Retrieved 2018/07/06.