2,3-Bis(4-hydroxyphenyl)propionitrile

Base Information

• Chemical Name: 2,3-Bis(4-hydroxyphenyl)propionitrile
• CAS No.: 1428-67-7
• Molecular Formula: C15H13 N O2
• Molecular Weight: 239.274
• European Community (EC) Number: 630-808-4
• UNII: 52XWB8Q4V8
• DSSTox Substance ID: DTXSID0040387
• Nikkaji Number: J40.780A
• Wikipedia: Diarylpropionitrile
• Wikidata: Q25100751
• Pharos Ligand ID: SJNF9D42K5BG
• Metabolomics Workbench ID: 63065
• ChEMBL ID: CHEMBL334773
• Mol file: 1428-67-7.mol

Synonyms:2,3-BHPPN;2,3-bis(4-hydroxyphenyl)-propionitrile;2,3-bis(p-hydroxyphenyl)propionitrile;diarylpropionitrile;DPN compound

Chemical Property of 2,3-Bis(4-hydroxyphenyl)propionitrile

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 1.08E-08mmHg at 25°C
• Melting Point: 200.0 to 204.0 °C
• Boiling Point: 449.4 °C at 760 mmHg
• Flash Point: 225.6 °C
• PSA: 64.25000
• Density: 1.256 g/cm³
• LogP: 2.94768
• Storage Temp.: Desiccate at -20°C
• Solubility.: DMSO: soluble10mg/mL, clear
• Water Solubility.: Soluble in 1eq. NaOH (30 mM), ethanol (100 mM), DMSO (100 mM), DMF (~30 mg/ml), and water (0.5 mg/ml at 25°C).
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 239.094628657
• Heavy Atom Count: 18
• Complexity: 293

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3-Bis(4-hydroxyphenyl)propionitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36-50
• Safety Statements: 26-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C#N)C2=CC=C(C=C2)O)O
• Description: DPN (1428-67-7) is a potent estrogen ERβ receptor agonist. Displays a 70-fold selectivity over ERα, EC50 = 0.85 and 66 nM, respectively.1 Regulates expression of GluR1, 2 and 3 in rat hippocampus.2 Ameliorates portal hypertension in a carbon tetrachloride-induced liver cirrhosis rat model.3 Stimulates proliferation of androgen-independent prostate cancer cell line PC-3 via a novel pathway involving ERβ-mediated activation of β-catenin.4 A useful tool for elucidating the biological function of ERβ.5
• Uses: 2,3-Bis(4-hydroxyphenyl)propionitrile is an estrogen receptor β and α specific with pro- and anti-nociceptive actions in mice.

Technology Process of 2,3-Bis(4-hydroxyphenyl)propionitrile

There total 6 articles about 2,3-Bis(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: 93.0%

2,3-bis(4-methoxyphenyl)propanenitrile (72035-46-2) → 2,3-bis-(4-hydroxyphenyl)propionitrile (1428-67-7)

Guidance literature:

With boron tribromide; In dichloromethane;

Reference yield:

p-methoxy-α-p-methoxyphenylcinnamonitrile (6443-74-9) → 2,3-bis-(4-hydroxyphenyl)propionitrile (1428-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate

2: boron tribromide / dichloromethane

With sodium tetrahydroborate; boron tribromide; In dichloromethane;

Reference yield:

p-methoxybenzylnitrile (104-47-2) → 2,3-bis-(4-hydroxyphenyl)propionitrile (1428-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / ethanol

2: sodium tetrahydroborate

3: boron tribromide / dichloromethane

With sodium tetrahydroborate; boron tribromide; potassium hydroxide; In ethanol; dichloromethane;

upstream raw materials:

2,3-bis(4-methoxyphenyl)propanenitrile

p-Methoxybenzyl bromide

p-methoxybenzylnitrile

p-methoxy-α-p-methoxyphenylcinnamonitrile

Refernces

• 1、 -. "ESTROGEN RECEPTOR LIGANDS, COMPOSITIONS AND METHODS RELATED THERETO". Page/Page column 36; 37. . Retrieved 2018/03/28.
• 2、 Meyers,Sun,Carlson,Marriner,Katzenellenbogen,Katzenellenbogen. "Estrogen receptor-β potency-selective ligands: Structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues". . p. 4230 - 4251. Retrieved 2007/10/03.