cis-2-Methyl-2-butenenitrile

Base Information

• Chemical Name: cis-2-Methyl-2-butenenitrile
• CAS No.: 20068-02-4
• Molecular Formula: C5H7N
• Molecular Weight: 81.1173
• Hs Code.: 2926909090
• European Community (EC) Number: 224-544-5,243-496-6
• UN Number: 3273
• UNII: RKI9CB99KR
• DSSTox Substance ID: DTXSID5027807
• Nikkaji Number: J280.434D
• ChEMBL ID: CHEMBL1884429
• Mol file: 20068-02-4.mol

Synonyms:Angeliconitrile;Angelic acid nitrile;cis-2-Methyl-2-butenenitrile;(Z)-2-Methyl-2-butenenitrile;2-Butenenitrile, 2-methyl-, (Z)-;2-Methyl-cis-2-butenenitrile;cis-2-Methyl-2-butenonitrile;angelonitrile;2-Butenenitrile, 2-methyl-, (2Z)-;20068-02-4;Crotononitrile, 2-methyl-, (Z)-;HSDB 6156;EINECS 243-496-6;RKI9CB99KR;2-Methylcrotononitrile;4403-61-6;alpha,beta-Dimethylacrylonitrile;CCRIS 6055;EINECS 224-544-5;UNII-RKI9CB99KR;CHEMBL1884429;DTXSID5027807;HSDB-6156;IHXNSHZBFXGOJM-HYXAFXHYSA-N;METHYL-2-BUTENENITRILE, (2Z)-;NCGC00090805-01;NCGC00090805-02;LS-165390

Chemical Property of cis-2-Methyl-2-butenenitrile

Chemical Property:

• Vapor Pressure: 13.2mmHg at 25°C
• Boiling Point: 123.6°Cat760mmHg
• Flash Point: 27.6°C
• PSA: 23.79000
• Density: 0.828g/cm³
• LogP: 1.47618
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 81.057849228
• Heavy Atom Count: 6
• Complexity: 102
• Transport DOT Label: Flammable Liquid Poison

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of cis-2-Methyl-2-butenenitrile

There total 26 articles about cis-2-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: 6.1%

2-METHYL-3-BUTENENITRILE (16529-56-9) → cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + (Z)-2-methyl-2-butenenitrile (20068-02-4) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + (Z)-pent-2-enenitrile (16545-78-1)

Guidance literature:

With C₁₄H₃₂P₂*2H^(1-)*2Ni⁽¹⁺⁾; In decane; at 100 ℃; for 3h; Solvent; Temperature; Reagent/catalyst; Kinetics; Inert atmosphere;

DOI:10.1021/ja8000216

Reference yield:

(Z)-2-Butene (590-18-1) + hydrogen cyanide (74-90-8) + hexanedinitrile (111-69-3) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + (Z)-2-methyl-2-butenenitrile (20068-02-4) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + 2-METHYL-3-BUTENENITRILE (16529-56-9) + 2-methylglutaronitrile (4553-62-2) + 4-ethenylcyclohexene (100-40-3) + (Z)-pent-2-enenitrile (16545-78-1)

Guidance literature:

(Z)-2-Butene; hydrogen cyanide; hexanedinitrile; buta-1,3-diene; C₄₂H₄₀O₆P₂; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; at 99.84 ℃;

nickel; at 109.84 ℃; Product distribution / selectivity;

Reference yield:

(Z)-2-Butene (590-18-1) + hydrogen cyanide (74-90-8) + hexanedinitrile (111-69-3) + 2-methylglutaronitrile (4553-62-2) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → cis-2-pentenenitrile (25899-50-7) + 2-pentenenitrile (26294-98-4) + 3-Pentenenitrile (16529-66-1) + (Z)-2-methyl-2-butenenitrile (20068-02-4) + tiglonitrile (30574-97-1) + 4-Pentenenitrile (592-51-8) + 2-METHYL-3-BUTENENITRILE (16529-56-9) + 4-ethenylcyclohexene (100-40-3) + (Z)-pent-2-enenitrile (16545-78-1)

Guidance literature:

C₄₈H₅₂O₄P₂; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; at 89.84 ℃; Product distribution / selectivity;

upstream raw materials:

quinoline

3-chloro-2-methyl-butyronitrile

2-chloromethyl-butyronitrile

2-hydroxy-2-methyl-butyronitrile

Downstream raw materials:

(Z)-2-Methyl-3-phenylsulfanyl-but-2-enenitrile

(E)-2-Methyl-3-phenylsulfanyl-but-2-enenitrile

(Z)-2-methyl-2-buteneamide

Angelic acid

Refernces

• 1、 -. "PROCESS FOR MAKING NITRILES". Page/Page column 54; 89-93. . Retrieved 2012/02/01.
• 2、 Tellew, John E.,Leith, Leslie,Mathur, Arvind. "Practical synthesis of 3-amino-4,5-dimethylisoxazole from 2-methyl-2-butenenitrile and acetohydroxamic acid". . p. 275 - 277. Retrieved 2012/12/26.