3-(4-Hydroxyphenyl)propionitrile

Base Information

• Chemical Name: 3-(4-Hydroxyphenyl)propionitrile
• CAS No.: 17362-17-3
• Molecular Formula: C9H9 N O
• Molecular Weight: 147.177
• Hs Code.: 2926909090
• European Community (EC) Number: 241-393-0
• NSC Number: 163340
• DSSTox Substance ID: DTXSID60938411
• Nikkaji Number: J30.665G
• Wikidata: Q72481128
• Mol file: 17362-17-3.mol

Synonyms:3-(4-Hydroxyphenyl)propionitrile;17362-17-3;3-(4-Hydroxyphenyl)propanenitrile;Benzenepropanenitrile, 4-hydroxy-;3-(p-Hydroxyphenyl)propiononitrile;4-hydroxyhydrocinnamonitrile;3-(4-hydroxyphenyl) propionitrile;EINECS 241-393-0;.beta.-(4-Hydroxyphenyl)propionitrile;NSC163340;p-Oxybenzylacetonitril;p-(2-Cyanoethyl)phenol;4-hydroxyphenylpropionitrile;SCHEMBL450038;DTXSID60938411;3-(4-hydroxyphenyl)proprionitrile;3-(p-hydroxyphenyl) propionitrile;3-(4-hydroxy-phenyl)-propionitrile;3-(4-Hydroxyphenyl)propanenitrile #;MFCD00016492;AKOS005199124;NSC 163340;NSC-163340;TS-01922;FT-0613677;FT-0613678;EN300-1853112;A811540

Chemical Property of 3-(4-Hydroxyphenyl)propionitrile

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 3.42E-05mmHg at 25°C
• Melting Point: 56-58°C
• Boiling Point: 166°C 8mm 344 °C at 760 mmHg
• PKA: 9.88±0.15(Predicted)
• Flash Point: 161.8 °C
• PSA: 44.02000
• Density: 1.127 g/cm³
• LogP: 1.84838
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

3-(4-Hydroxyphenyl)propionitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC#N)O
• Uses: 3-(4-Hydroxyphenyl)propionitrile is commonly used as a tool to evaluate the biological role of ERβ.

Technology Process of 3-(4-Hydroxyphenyl)propionitrile

There total 24 articles about 3-(4-Hydroxyphenyl)propionitrile 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: 91.0%

4-hydroxyphenylacetate (156-38-7) + trimethylsilyl cyanide (7677-24-9) → 3-(p-hydroxyphenyl)propiononitrile (17362-17-3)

Guidance literature:

4-hydroxyphenylacetate; With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; iodine; In chloroform; at 60 ℃; Inert atmosphere;

trimethylsilyl cyanide; With tetrabutyl ammonium fluoride; In tetrahydrofuran; chloroform; at 60 ℃; for 5h; Reagent/catalyst; chemoselective reaction; Inert atmosphere;

DOI:10.1055/s-0033-1339903

Reference yield: 75.0%

3-(4-hydroxyphenyl)-2-(phenylsulfonyl)propanenitrile → 3-(p-hydroxyphenyl)propiononitrile (17362-17-3)

Guidance literature:

With chloro-trimethyl-silane; bis(pentamethylcyclopentadienyl)titanium dichloride; 2,4,6-collidine hydrochloride; zinc(II) chloride; zinc; In toluene; at 110 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.202005400

Reference yield: 74.0%

acrylonitrile (107-13-1,25014-41-9) + phenol (108-95-2,27073-41-2) → 3-(p-hydroxyphenyl)propiononitrile (17362-17-3)

Guidance literature:

With hydrogenchloride; aluminium trichloride; for 2h; Heating;

DOI:10.1016/j.bmc.2005.01.016

upstream raw materials:

3-(4-acetoxyphenyl)propanenitrile

3-(4-aminophenyl)-propionitrile

acrylonitrile

phenol

Downstream raw materials:

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on

4-(5-Hexyl-pyrimidin-2-yl)-benzoic acid 4-(2-cyano-ethyl)-phenyl ester

3-[4-(4-Acetyl-2-ethyl-3-hydroxy-benzyloxy)-phenyl]-propionitrile

3-[4-(4-Acetyl-3-hydroxy-2-propyl-benzyloxy)-phenyl]-propionitrile

Refernces

• 1、 Yi, Ce,Xing, Gang,Wang, Siqi,Li, Xiaoran,Liu, Yichuang,Li, Jinyan,Lin, Bin,Woo, Anthony Yiu-Ho,Zhang, Yuyang,Pan, Li,Cheng, Maosheng. "Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists". . . Retrieved 2019/11/26.
• 2、 -. "CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF". Page/Page column 10. . Retrieved 2014/10/15.