3-Pentenenitrile

Base Information

• Chemical Name: 3-Pentenenitrile
• CAS No.: 16529-66-1
• Molecular Formula: C5H7 N
• Molecular Weight: 81.1173
• European Community (EC) Number: 225-060-7,605-402-5
• UN Number: 3275
• UNII: 80L2GJH2P2
• DSSTox Substance ID: DTXSID901019314
• Nikkaji Number: J298.912C,J38.121G
• Wikidata: Q27269157
• Metabolomics Workbench ID: 123305
• ChEMBL ID: CHEMBL1322495
• Mol file: 16529-66-1.mol

Synonyms:4 pentenenitrile;4-pentenenitrile;trans-3-pentenenitrile

Chemical Property of 3-Pentenenitrile

Chemical Property:

• Vapor Pressure: 24.9 mm Hg ( 50 °C)
• Refractive Index: n20/D 1.422
• Boiling Point: 112°Cat760mmHg
• Flash Point: 28.5°C
• PSA: 23.79000
• Density: 0.827g/cm³
• LogP: 1.47618
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 81.057849228
• Heavy Atom Count: 6
• Complexity: 83.4
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

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

3-Pentenenitrile, predominately trans 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 10-23/24/25-36/37/38-23-22
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC=CCC#N
• Isomeric SMILES: C/C=C/CC#N
• General Description: 3-Pentenenitrile is an unsaturated nitrile whose chemoselective hydrogenation behavior is influenced by the position and substitution of its double bond relative to the nitrile group. The study indicates that higher selectivity for unsaturated amines is achieved when the double bond is not conjugated with the nitrile group and is located farther 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 the C=C bond more readily.

Technology Process of 3-Pentenenitrile

There total 41 articles about 3-Pentenenitrile 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: 17.8%

thiophene (188290-36-0,8014-23-1,25233-34-5) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 3-Pentenenitrile (16529-66-1) + 2-METHYL-3-BUTENENITRILE (16529-56-9)

Guidance literature:

With hydrogen isocyanide; copper(I) bromide;

Reference yield: 6.1%

2-METHYL-3-BUTENENITRILE (16529-56-9) → cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + (Z)-2-methyl-2-butenenitrile (20068-02-4) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + (Z)-pent-2-enenitrile (16545-78-1)

Guidance literature:

With C₁₄H₃₂P₂*2H^(1-)*2Ni⁽¹⁺⁾; In decane; at 100 ℃; for 3h; Solvent; Temperature; Reagent/catalyst; Kinetics; Inert atmosphere;

DOI:10.1021/ja8000216

Reference yield:

hydrogen cyanide (74-90-8) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 2-pentenenitrile (13284-42-9) + 3-Pentenenitrile (16529-66-1) + 4-Pentenenitrile (592-51-8) + 2-METHYL-3-BUTENENITRILE (16529-56-9)

Guidance literature:

(Phosphite A)Ni(crotyl)CN; at 110 - 130 ℃; for 14 - 48.2h; under 5171.62 - 6723.1 Torr; Product distribution / selectivity;

upstream raw materials:

2-chloro-3-butene

hydrogen cyanide

(E)-diethyl (but-2-en-1-yl)malonate

(E)-1-Bromo-2-butene

Downstream raw materials:

5-methyl-dihydro-furan-2-one

2-cyclohexylidene-pent-3t-enenitrile

2-((Ξ)-benzylidene)-pent-3t-enenitrile

2-(4-methoxy-benzylidene)-pent-3t-enenitrile

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.