2-Pentenenitrile

Base Information

• Chemical Name: 2-Pentenenitrile
• CAS No.: 13284-42-9
• Molecular Formula: C5H7 N
• Molecular Weight: 81.1173
• Hs Code.: 2926909090
• European Community (EC) Number: 236-297-0,247-593-4
• UN Number: 3275
• UNII: 1VA047EULA
• Nikkaji Number: J181.276I,J102.106K
• Wikidata: Q27252950
• Metabolomics Workbench ID: 126915
• ChEMBL ID: CHEMBL2138413
• Mol file: 13284-42-9.mol

Synonyms:2-pentenenitrile;2-pentenenitrile, (E)-isomer;2-pentenenitrile, (Z)-isomer

Chemical Property of 2-Pentenenitrile

Chemical Property:

• Vapor Pressure: 22.2mmHg at 25°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: 1.2
• 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

2-Pentenenitrile >90.0%(GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 10-23/24/25
• Safety Statements: 16-28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC=CC#N
• Isomeric SMILES: CC/C=C/C#N
• General Description: 2-Pentenenitrile, also known as 1-cyano-1-butene, is an unsaturated nitrile whose hydrogenation behavior is influenced by the position and substitution of its double bond relative to the nitrile group. The study indicates that its selectivity for forming unsaturated amines during hydrogenation depends on the non-conjugation of the double bond with the nitrile group, with greater distance between the C=C and C≡N groups enhancing selectivity. Additionally, increased substitution at the C=C bond further improves selectivity. Raney cobalt, particularly Cr-doped Raney cobalt, is more effective for this chemoselective hydrogenation compared to Raney nickel, which tends to hydrogenate the C=C bond more readily.

Technology Process of 2-Pentenenitrile

There total 20 articles about 2-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: 10.0%

3-pentenenitrile (4635-87-4) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-pentenenitrile (13284-42-9) + hexanedinitrile (111-69-3)

Guidance literature:

With Lewis acid; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₆₈H₈₀O₆P₂; In tetrahydrofuran; at 90 ℃; for 4h;

Reference yield:

quinoline (91-22-5) + 3-chloro-valeronitrile (88725-90-0) → 2-pentenenitrile (13284-42-9)

Guidance literature:

Reference yield:

quinoline (91-22-5) + 1-chloro-2-cyanobutane (22819-90-5) → 2-pentenenitrile (13284-42-9)

Guidance literature:

upstream raw materials:

quinoline

3-chloro-valeronitrile

1-chloro-2-cyanobutane

1-Cyanobutanol

Downstream raw materials:

trans-2-pentenoic acid

(Z)-2-pentenoic acid

hexanedinitrile

4-Pentenenitrile

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.

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