4-Chloro-3-methylbut-2-enenitrile

Base Information

• Chemical Name: 4-Chloro-3-methylbut-2-enenitrile
• CAS No.: 4450-34-4
• Molecular Formula: C₅H₆ClN
• Molecular Weight: 115.562
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID20696545
• Mol file: 4450-34-4.mol

Synonyms:4-Chloro-3-methylbut-2-enenitrile;DTXSID20696545;3-methyl-4-chloro-2-butenonitrile;AKOS030242108;FT-0664778

Chemical Property of 4-Chloro-3-methylbut-2-enenitrile

Chemical Property:

• Vapor Pressure: 0.221mmHg at 25°C
• Refractive Index: 1.459
• Boiling Point: 207.802°C at 760 mmHg
• Flash Point: 87.447°C
• PSA: 23.79000
• Density: 1.058g/cm³
• LogP: 1.69508
• Storage Temp.: Amber Vial, -20?C Freezer
• Solubility.: Chloroform, Dichloromethane, Ether, Ethyl Acetate,
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 115.0188769
• Heavy Atom Count: 7
• Complexity: 117

Purity/Quality:

99%min ^*data from raw suppliers

4-Chloro-3-methy-2-butenenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC#N)CCl
• Uses: This item is a cis trans mixture.

Technology Process of 4-Chloro-3-methylbut-2-enenitrile

There total 4 articles about 4-Chloro-3-methylbut-2-enenitrile 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: 50.0%

2-hydroxy-3-methylbut-3-enenitrile (22410-56-6,147600-17-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-chloro-3-methyl-2-butenenitrile (4450-34-4) + 2-chloro-3-methyl-3-butenenitrile (123810-33-3)

Guidance literature:

With oxalyl dichloride; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1021/jo00289a034

Reference yield: 33.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + chloroacetone (78-95-5) → 4-chloro-3-methyl-2-butenenitrile (4450-34-4)

Guidance literature:

With sodium hydroxide; In diethyl ether; at 20 ℃; for 5h; Reflux; Inert atmosphere;

DOI:10.1021/ja3007929

Reference yield:

4-chloro-3-methyl-but-3-enenitrile (7659-48-5) → 4-chloro-3-methyl-2-butenenitrile (4450-34-4)

Guidance literature:

With sodium phenoxide; phenol;

upstream raw materials:

4-chloro-3-methyl-but-3-enenitrile

2-hydroxy-3-methylbut-3-enenitrile

N,N-dimethyl-formamide

diethyl 1-cyanomethylphosphonate

Downstream raw materials:

6-methyl-5H-pyrrolo<1,2-d>tetrazole

7-cis,11-cis-retinonitrile

7-Cis,11-cis,13-cis-retinonitrile

7-cis,9-cis-retinonitrile

Refernces

• 1、 Sovdat, Tina,Bassolino, Giovanni,Liebel, Matz,Schnedermann, Christoph,Fletcher, Stephen P.,Kukura, Philipp. "Backbone modification of retinal induces protein-like excited state dynamics in solution". supporting information; experimental part. p. 8318 - 8320. Retrieved 2012/06/30.
• 2、 Trehan,Mirzadegan,Liu. "The doubly hindered 7,11-dicis, 7,9,11-tricis, 7,11,13-tricis and all-cis isomers of retinonitrile and retinal". . p. 3769 - 3780. Retrieved 2007/10/02.