2-Hydroxy-4-phenylbutanenitrile

Base Information

• Chemical Name: 2-Hydroxy-4-phenylbutanenitrile
• CAS No.: 53279-92-8
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.203
• DSSTox Substance ID: DTXSID90447980
• Nikkaji Number: J261.945H
• Mol file: 53279-92-8.mol

Synonyms:2-hydroxy-4-phenylbutanenitrile;2-hydroxy-4-phenylbutyronitrile;53279-92-8;SCHEMBL2163440;alpha-Hydroxybenzenebutanenitrile;2-hydroxy-4-phenyl-butyronitrile;DTXSID90447980;CUJUQPVHWIDESZ-UHFFFAOYSA-N;alpha-Cyano-3-phenylpropyl alcohol;AKOS012176331;(r,s)-2-hydroxy-4-phenylbutyronitrile

Chemical Property of 2-Hydroxy-4-phenylbutanenitrile

Chemical Property:

• PSA: 44.02000
• LogP: 1.50368
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C#N)O

Technology Process of 2-Hydroxy-4-phenylbutanenitrile

There total 15 articles about 2-Hydroxy-4-phenylbutanenitrile 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: 88.0%

3-phenyl-propionaldehyde (104-53-0) + trimethylsilyl cyanide (7677-24-9) → (S)-2-hydroxy-4-phenylbutyronitrile (53279-92-8,120999-41-9,121054-03-3,117213-74-8) + (R)-2-hydroxy-4-phenylbutanenitrile (120999-41-9)

Guidance literature:

With titanium(IV) dichlorodiisopropylate; (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol; In toluene; at -78 ℃; for 20h; Title compound not separated from byproducts;

DOI:10.1246/bcsj.61.4379

Reference yield: 61.0%

3-phenyl-propionaldehyde (104-53-0) + trimethylsilyl cyanide (7677-24-9) → (S)-2-hydroxy-4-phenylbutyronitrile (53279-92-8,120999-41-9,121054-03-3,117213-74-8)

Guidance literature:

3-phenyl-propionaldehyde; trimethylsilyl cyanide; With 4 A molecular sieve; titanium(IV) isopropylate; (1R,2R)-N,N'-bis[(1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylcarbonyl]-1,2-diphenylethylenediamine; In dichloromethane; at -78 ℃;

With hydrogenchloride; In dichloromethane; for 6h; Further stages.;

DOI:10.1039/b107867d

Reference yield: 45.0%

acetic acid 1-cyano-3-phenylpropyl ester (119798-23-1) → (S)-2-hydroxy-4-phenylbutyronitrile (53279-92-8,120999-41-9,121054-03-3,117213-74-8)

Guidance literature:

With Pseudomonas fluorescens Amano lipase; In tetrahydrofuran; water; Enzymatic reaction;

DOI:10.1016/j.crci.2016.11.006

upstream raw materials:

3-phenyl-propionaldehyde

trimethylsilyl cyanide

vinyl acetate

2-hydroxy-4-phenylbutanenitrile

Downstream raw materials:

(S)-1-cyano-3-phenylpropyl diisopropylcarbamate

(R)-2-cyano-1-ethoxy-1-oxo-4-phenylbutan-2-yl pyrrolidine-1-carboxylate

(R)-3-cyano-5,5-dimethyl-4-oxo-1-phenylhexan-3-yl dimethylcarbamate

(R)-3-cyano-5-methyl-4-oxo-1-phenylhexan-3-yl dimethylcarbamate

Refernces

• 1、 Delville, Marille M. E.,Koch, Kaspar,Van Hest, Jan C. M.,Rutjes, Floris P. J. T.. "Chemoenzymatic flow cascade for the synthesis of protected mandelonitrile derivatives". supporting information. p. 1634 - 1638. Retrieved 2015/03/05.
• 2、 -. "(R)-selective hydroxynitrile lyase variants with a cupin fold having improved substrate scope and the use thereof". Paragraph 0082; 0083. . Retrieved 2015/12/31.