3-Methyl-2-butenenitrile

Base Information

• Chemical Name: 3-Methyl-2-butenenitrile
• CAS No.: 4786-24-7
• Molecular Formula: C5H7N
• Molecular Weight: 81.1173
• European Community (EC) Number: 225-336-7
• NSC Number: 221457
• UNII: KLX2QO8EUY
• DSSTox Substance ID: DTXSID40197307
• Nikkaji Number: J262.453B
• Mol file: 4786-24-7.mol

Synonyms:3-methyl-2-butenenitrile;Me-butenenitrile

Chemical Property of 3-Methyl-2-butenenitrile

Chemical Property:

• Vapor Pressure: 13.2mmHg at 25°C
• Refractive Index: 1.425
• Boiling Point: 123.6 °C at 760 mmHg
• Flash Point: 27.6 °C
• PSA: 23.79000
• Density: 0.828 g/cm³
• LogP: 1.47618
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 81.057849228
• Heavy Atom Count: 6
• Complexity: 98.4

Purity/Quality:

97% ^*data from raw suppliers

3-METHYL CROTONONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC#N)C
• General Description: 3-Methylcrotononitrile (3-methylbut-2-enenitrile) is an unsaturated nitrile whose chemoselective hydrogenation behavior can be inferred from the study's findings. The selectivity for unsaturated amines during hydrogenation is influenced by the position and substitution of the double bond relative to the nitrile group. Specifically, higher selectivity is achieved when the double bond is not conjugated with the nitrile and when the C=C bond is farther from the C≡N group. 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-Methyl-2-butenenitrile

There total 25 articles about 3-Methyl-2-butenenitrile 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: 92.0%

2-methylprop-1-enyl chloride (513-37-1) + potassium cyanide (151-50-8) → 3,3-dimethylacrylonitrile (4786-24-7)

Guidance literature:

With potassium hydroxide; hydrogen; In water; at 45 ℃; for 1h;

DOI:10.1021/ja00370a019

Reference yield: 87.0%

2-methylprop-1-enyl chloride (513-37-1) + sodium cyanide (143-33-9,25596-52-5) → 3,3-dimethylacrylonitrile (4786-24-7)

Guidance literature:

With dibromobis(triphenylphosphine)nickel(II); triphenylphosphine; zinc; In N,N-dimethyl-formamide; at 50 ℃; for 8h;

DOI:10.1246/bcsj.68.3137

Reference yield: 80.0%

2-methyl-1-propenylbromide (3017-69-4) + potassium cyanide (151-50-8) → 3,3-dimethylacrylonitrile (4786-24-7)

Guidance literature:

With potassium hydroxide; hydrogen; cobalt(II) chloride; In water; at 45 ℃; for 6h;

DOI:10.1021/ja00370a019

upstream raw materials:

pyridine

2-cyano-3-methylbut-2-enoic acid

2-hydroxy-3-methylbutanenitrile

3-hydroxy-3-methylbutyronitrile

Downstream raw materials:

2-ethyl-3-methyl-crotononitrile

2-ethyl-3-methyl-hex-2-enenitrile

1-amino-3-methylbutane

Isovaleronitrile

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.