(Z)-2-hydroxypent-3-enenitrile

Base Information

• Chemical Name: (Z)-2-hydroxypent-3-enenitrile
• CAS No.: 6812-26-6
• Molecular Formula: C5H7NO
• Molecular Weight: 97.1152
• NSC Number: 57751
• DSSTox Substance ID: DTXSID00418121
• Mol file: 6812-26-6.mol

Synonyms:6812-26-6;(Z)-2-hydroxypent-3-enenitrile;NSC57751;DTXSID00418121;NSC-57751

Chemical Property of (Z)-2-hydroxypent-3-enenitrile

Chemical Property:

• Vapor Pressure: 0.0372mmHg at 25°C
• Boiling Point: 213.1°C at 760 mmHg
• Flash Point: 82.7°C
• Density: 1.012g/cm³
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 97.052763847
• Heavy Atom Count: 7
• Complexity: 109

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(C#N)O
• Isomeric SMILES: C/C=C\C(C#N)O

Technology Process of (Z)-2-hydroxypent-3-enenitrile

There total 13 articles about (Z)-2-hydroxypent-3-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: 86.0%

trimethylsilyl cyanide (7677-24-9) + crotonaldehyde (123-73-9,4170-30-3) → C5H7NO (6812-26-6)

Guidance literature:

With tris(pentafluorophenyl)borate; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1124/dmd.114.060459

Reference yield: 72.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + potassium cyanide (151-50-8) → (R)-(-)-2-hydroxy-3-(E)-pentenenitrile (6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6)

Guidance literature:

potassium cyanide; With hydrogenchloride; pH=1; cooling;

trans-Crotonaldehyde; With defatted almond meal oxynitrilase; In di-isopropyl ether; at 2 ℃; for 12h;

DOI:10.1016/j.tetasy.2005.03.018

Reference yield: 70.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (R)-(-)-2-hydroxy-3-(E)-pentenenitrile (6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6)

Guidance literature:

With Prunus mume (R)-hydroxynitrile lyase; Na-citrate buffer; In di-isopropyl ether; at 25 ℃; for 14h; pH=4.0;

DOI:10.1016/j.tetasy.2006.02.003

upstream raw materials:

trans-Crotonaldehyde

hydrogen cyanide

trimethylsilyl cyanide

potassium cyanide

Downstream raw materials:

(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate