(E)-3-Amino-2-butenenitrile

Base Information

• Chemical Name: (E)-3-Amino-2-butenenitrile
• CAS No.: 763-33-7
• Molecular Formula: C4H6N2
• Molecular Weight: 82.105
• European Community (EC) Number: 214-266-2
• NSC Number: 102759
• UNII: M4Z658J7FD
• DSSTox Substance ID: DTXSID001309025
• Nikkaji Number: J79.935A
• Mol file: 763-33-7.mol

Synonyms:3-aminocrotonitrile;

Chemical Property of (E)-3-Amino-2-butenenitrile

Chemical Property:

• Boiling Point: 276.3±13.0 °C(Predicted)
• PKA: 3.88±0.70(Predicted)
• PSA: 49.81000
• Density: 0.965±0.06 g/cm3(Predicted)
• LogP: 1.07278
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 82.053098200
• Heavy Atom Count: 6
• Complexity: 104

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(=CC#N)N
• Isomeric SMILES: C/C(=C\C#N)/N

Technology Process of (E)-3-Amino-2-butenenitrile

There total 8 articles about (E)-3-Amino-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: 22.0%

acetonitrile (75-05-8,26809-02-9) → (E)-3-aminocrotononitrile (763-33-7)

Guidance literature:

With sodium; In benzene; for 3h; Heating;

DOI:10.1039/P29830000175

Reference yield: 1.34%

2-butynenitrile (13752-78-8) → 2-aminocrotononitrile (870-64-4) + (E)-3-aminocrotononitrile (763-33-7)

Guidance literature:

With ammonia; at 25 ℃; for 0.166667h; Title compound not separated from byproducts; Irradiation;

DOI:10.1002/(SICI)1521-3765(19980615)4:6<1074::AID-CHEM1074>3.0.CO;2-B

Reference yield:

acetonitrile (75-05-8,26809-02-9) → 4-amino-2,6-dimethylpyrimidine (461-98-3) + (E)-3-aminocrotononitrile (763-33-7)

Guidance literature:

With (Ph₃Ge)3GeNMe₂; triphenylgermane; at 90 ℃; for 72h; Inert atmosphere;

DOI:10.1021/om101091c

upstream raw materials:

buta-2,3-dienenitrile

diethyl ether

ethylmagnesium bromide

acetonitrile

Downstream raw materials:

β-cyclohexylamino-cis-crotonitril

N-phenyl-β-aminocrotononitrile

N-benzyl-β-aminocrotononitrile

3-morpholino crotonitrile

Refernces

• 1、 Li, Yinghua,Zhu, Yingzu,Xiang, Shiqun,Fan, Weibin,Jin, Jiang,Huang, Deguang. "Temperature controlled condensation of nitriles: Efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system". . p. 6576 - 6583. Retrieved 2020/02/25.
• 2、 Guillemin, Jean-Claude,Breneman, Curt M.,Joseph, Jeffrey C.,Ferris, James P.. "Regioselectivity of the photochemical addition of ammonia, phosphine, and silane to olefinic and acetylenic nitriles". . p. 1074 - 1082. Retrieved 2007/10/03.