2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

Base Information

• Chemical Name: 2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile
• CAS No.: 39515-47-4
• Deprecated CAS: 52315-06-7,66775-58-4
• Molecular Formula: C14H11NO2
• Molecular Weight: 225.247
• Hs Code.: 2926909090
• European Community (EC) Number: 257-841-3,254-486-6
• DSSTox Substance ID: DTXSID00885773
• Nikkaji Number: J43.143E,J274.182B
• Wikidata: Q82864459
• Mol file: 39515-47-4.mol

Synonyms:alpha-hydroxy-3-phenoxybenzeneacetonitrile;HPBAN cpd;hydroxy-3-phenoxybenzeneacetonitrile

Chemical Property of 2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

Chemical Property:

• Appearance/Colour: clear orange solution
• Melting Point: 79℃ (ethanol )
• Boiling Point: 399.8 °C at 760 mmHg
• PKA: 10.33±0.20(Predicted)
• Flash Point: 195.6 °C
• PSA: 53.25000
• Density: 1.22 g/cm³
• LogP: 3.03588
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform, DMSO
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 225.078978594
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

98%min ^*data from raw suppliers

α-Hydroxy-3-phenoxybenzeneacetonitrile(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=CC(=C2)C(C#N)O
• Uses: α-Hydroxy-3-phenoxybenzeneacetonitrile is an intermediate in synthesizing τ-Fluvalinate (F601100), a synthetic pyrethroid aracacide. τ-Fluvalinate is commonly used to control Varroa jacobsoni (a parasitic mite) in honey bee colonies.

Technology Process of 2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

There total 47 articles about 2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile 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: 99.0%

hydrogen cyanide (74-90-8) + 3-Phenoxybenzaldehyde (39515-51-0) → (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8)

Guidance literature:

With hydroxynitrile lyase from Hevea brasiliensis; In water; at 15 ℃; for 0.25h; pH 5.5;

DOI:10.1016/S0040-4020(98)00901-6

Reference yield: 92.0%

O-acetyl-(S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (113301-28-3) → (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8)

Guidance literature:

With ethanol; In di-isopropyl ether; at 25 ℃; for 6h; lipase from Pseudomonas cepacia (Amano);

DOI:10.1021/jo00047a016

Reference yield: 85.0%

(R,S)-cyano(3-phenoxyphenyl)methyl butyrate (120838-94-0) → (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8) + (R)-cyano(3-phenoxyphenyl)methyl butanoate

Guidance literature:

With Pseudomonas cepacia lipase immobilised in a gelatin matrix; butan-1-ol; In hexane; for 8h;

DOI:10.1016/S0957-4166(00)00303-7

upstream raw materials:

O-acetyl-(S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

hydrogen cyanide

3-Phenoxybenzaldehyde

sodium cyanide

Downstream raw materials:

3'-Phenoxy-α'-cyanobenzyl-α-ethyl-phenylacetat

dimethylsulfide

cis-3-(2-Methyl-1-propenyl)-2,2-bis(trifluormethyl)cyclopropancarbonsaeure-(α-cyan-3-phenoxybenzyl)ester

trans-3-(2-Methyl-1-propenyl)-2,2-bis(trifluormethyl)cyclopropancarbonsaeure-(α-cyan-3-phenoxybenzyl)ester

Refernces

• 1、 Shvo, Youval,Gal, Meir,Becker, Yigal,Elgavi, Asher. "Asymmetric hydrocyanation of aldehydes with cyclo-dipeptides: A new mechanistic approach". . p. 911 - 924. Retrieved 1996.
• 2、 Jangir, Nisha,Preeti,Padhi, Santosh Kumar. "A study on increasing enzymatic stability and activity of Baliospermum montanum hydroxynitrile lyase in biocatalysis". . p. 78 - 89. Retrieved 2019/11/05.
• 3、 -. "PYRETHROID COMPOUND, AND HAIR RESTORER AND HAIR RESTORER COMPOSITION COMPRISING THE SAME". Paragraph 0032; 0036. . Retrieved 2017/08/26.