2,6-Octadienenitrile, 3,7-dimethyl-

Base Information

• Chemical Name: 2,6-Octadienenitrile, 3,7-dimethyl-
• CAS No.: 5146-66-7
• Deprecated CAS: 80655-58-9,80748-12-5
• Molecular Formula: C10H15N
• Molecular Weight: 149.236
• Hs Code.: 29269095
• DSSTox Substance ID: DTXSID3036286
• Wikidata: Q2700125
• ChEMBL ID: CHEMBL3185090
• Mol file: 5146-66-7.mol

Synonyms:citronitrile;2,6-Octadienenitrile, 3,7-dimethyl-;DTXSID3036286;(Z) - 3,7 - dimethylocta - 2,6 - dienenitrile;CHEMBL3185090;AKOS028109913;LS-97788;FT-0626651;FT-0626670;FT-0626671;Q2700125

Chemical Property of 2,6-Octadienenitrile, 3,7-dimethyl-

Chemical Property:

• Appearance/Colour: clear yellow 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: 0.859 g/cm³
• LogP: 3.20268
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: SLIGHTLY SOLUBLE
• 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:

98% ^*data from raw suppliers

GeranylNitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 51/53-68-20/21
• Safety Statements: 36/37-61-23

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CC#N)C)C
• General Description: 3,7-Dimethyl-2,6-octadienenitrile (geranylnitrile) is an unsaturated nitrile whose chemoselective hydrogenation behavior is influenced by the position and substitution of its double bonds relative to the nitrile group. The study found that selectivity for unsaturated amines is higher when the double bonds are not conjugated with the nitrile group and when they are further away from it. Additionally, increased substitution at the C=C bond enhances selectivity. Raney cobalt, particularly Cr-doped Raney cobalt, is more effective for selective hydrogenation compared to Raney nickel, which tends to hydrogenate C=C bonds more readily. These structural and catalytic insights are relevant for optimizing hydrogenation conditions for similar unsaturated nitriles.

Technology Process of 2,6-Octadienenitrile, 3,7-dimethyl-

There total 13 articles about 2,6-Octadienenitrile, 3,7-dimethyl- 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%

geraniol (624-15-7) → geranonitrile (5146-66-7,80748-12-5)

Guidance literature:

With ammonia; oxygen; In tert-Amyl alcohol; water; at 100 ℃; for 24h; under 3750.38 Torr; Autoclave; High pressure;

DOI:10.1021/acscatal.0c00485

Reference yield: 90.0%

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → geranonitrile (5146-66-7,80748-12-5)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In acetonitrile; for 14h; Reflux;

DOI:10.1016/j.tetlet.2012.04.057

Reference yield: 90.0%

3,7-dimethylocta-2,6-dienal oxime (13372-77-5) → geranonitrile (5146-66-7,80748-12-5)

Guidance literature:

With S,S-dimethyl dithiocarbonate; triethylamine; In 1,4-dioxane; at 90 ℃;

DOI:10.1055/s-2004-830878

upstream raw materials:

3,7-dimethylocta-2,6-dienal oxime

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

cyanoacetic acid

(E/Z)-3,7-dimethyl-2,6-octadienal

Downstream raw materials:

(1,5-Dimethyl-hex-4-enylidene)-cyclohexane

citronellylnitrile

2,2,6-trimethyl-1-cyclohexenylcarbonitrile

2,6,6-trimethyl-2-cyclohexenecarbonitrile

Refernces

Structure-selectivity relationship in the chemoselective hydrogenation of unsaturated nitriles

10.1016/j.jcat.2005.06.011

The research investigates the structure-selectivity relationship in the chemoselective hydrogenation of various unsaturated nitriles using different catalysts. The purpose of the study was to understand how the molecular structure of substrates influences the selectivity for unsaturated amines and to explore the scope and limitations of this type of hydrogenation. The researchers used several unsaturated nitriles, including cinnamonitrile, cyclohex-1-enyl-acetonitrile, acrylonitrile, 3,3-dimethyl-acrylonitrile, geranylnitrile, and 2- and 3-pentenenitrile, which were hydrogenated over Cr-doped Raney cobalt and nickel, as well as their undoped equivalents. The conclusions drawn from the study were that the position of the double bond relative to the nitrile group and the substitution of the double bond are crucial factors in determining the chemoselectivity for unsaturated amines. The highest selectivities were obtained when the double bond was not conjugated with the nitrile group, and the further the C=C bond was from the C≡N group, the higher the selectivity. Additionally, the presence of more substituents at the C=C bond increased the selectivity for unsaturated amines. The study also highlighted the suitability of Raney cobalt, especially Cr-doped Raney cobalt, for the chemoselective hydrogenation of unsaturated nitriles, while Raney nickel catalysts were found to be less selective due to their higher activity in C=C bond hydrogenation.