Crotononitrile

Base Information

• Chemical Name: Crotononitrile
• CAS No.: 627-26-9
• Molecular Formula: C₄H₅N
• Molecular Weight: 67.0904
• European Community (EC) Number: 225-335-1,811-029-0
• UN Number: 2924
• UNII: E74GS2HL23
• DSSTox Substance ID: DTXSID0063604,DTXSID801026544
• Nikkaji Number: J42.317C,J512F
• Wikidata: Q2672058
• ChEMBL ID: CHEMBL4748537
• Mol file: 627-26-9.mol

Synonyms:2-butenenitrile;crotononitrile;crotononitrile, (E)-isomer;crotononitrile, (Z)-isomer

Chemical Property of Crotononitrile

Chemical Property:

• Melting Point: -51.15°C
• Refractive Index: 1.4190 to 1.4220
• Boiling Point: 108.92°C (estimate)
• Flash Point: 16°C(lit.)
• PSA: 23.79000
• Density: 0.8070
• LogP: 1.08608
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 67.042199164
• Heavy Atom Count: 5
• Complexity: 72.9

Purity/Quality:

99%, ^*data from raw suppliers

(E)-But-2-enenitrile ^*data from reagent suppliers

Safty Information:

• Safety Statements: A poison. Very reactive. A very dangerous fire hazard when exposed to heat or flame."> −. See also CYANIDE." target="_blank">A poison. Very reactive. A very dangerous fire hazard when exposed to heat or flame.

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Crotononitrile

There total 236 articles about Crotononitrile 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: 78.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) → crotononitrile (4786-20-3,627-26-9)

Guidance literature:

With aluminum oxide; potassium fluoride; hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 100 ℃; for 9h;

DOI:10.1016/j.tetlet.2005.08.007

Reference yield: 30.0%

cis-4-cyano-3-methyl-1-(p-tolyl)azetidin-2-one → (Z)-2-butenenitrile (1190-76-7,627-26-9) + crotononitrile (4786-20-3,627-26-9) + (p-tolyl)iminoacetonitrile (1204614-43-6) + p-Tolylisocyanate (622-58-2,374675-64-6)

Guidance literature:

at 720 ℃; under 0.0015 Torr; regioselective reaction;

DOI:10.1016/j.tet.2009.10.080

Reference yield: 30.0%

cis-4-cyano-3-methyl-1-(p-tolyl)azetidin-2-one → (Z)-2-butenenitrile (1190-76-7,627-26-9) + crotononitrile (4786-20-3,627-26-9) + (p-tolyl)iminoacetonitrile (1204614-43-6) + p-Tolylisocyanate (622-58-2,374675-64-6)

Guidance literature:

at 720 ℃; under 0.0015 Torr; regioselective reaction;

DOI:10.1016/j.tet.2009.10.080

upstream raw materials:

4-Chlorobutyronitrile

2-hydroxybutanenitrile

(+-)-3-amino-butyronitrile

3-hydroxybutanenitrile

Downstream raw materials:

3-tosylbutanenitrile

N-<3-Cyanpropyl-(2)>-DL-phenylalanin

β-chloro-γ-(4-chloro-o-tolyl)butyronitrile

trans-3-(4'-tert-butylcyclohexyl)butyronitrile

Refernces

• 1、 -. "LJ reaction in the preparation wittich reagent and application of glufosinate in". Paragraph 0094; 0095. . Retrieved 2017/12/04.
• 2、 Cai, Chaoxian,Yu, Shichao,Cao, Bonan,Zhang, Xumu. "New tetraphosphorus ligands for highly linear selective hydroformylation of allyl and vinyl derivatives". experimental part. p. 9992 - 9998. Retrieved 2012/09/07.