72035-46-2

Usage

Nitrile derivative

2,3-bis(4-methoxyphenyl)propanenitrile is derived from 4-methoxyphenylpropanol, a type of alcohol, by replacing the hydroxyl group (-OH) with a nitrile group (-C≡N).

Ligands for catalytic reactions

The compound is commonly used as a ligand, a molecule that binds to a metal catalyst to facilitate a chemical reaction, and enhances its activity and selectivity.

Building block in organic synthesis

2,3-bis(4-methoxyphenyl)propanenitrile is used as a starting material to build more complex organic molecules through chemical reactions.

White to off-white solid at room temperature

The compound is a solid at room temperature and has a white to off-white color.

Insoluble in water

The compound does not dissolve in water, which can affect its solubility and reactivity in aqueous solutions.

Soluble in organic solvents

2,3-bis(4-methoxyphenyl)propanenitrile dissolves in organic solvents such as ethanol and acetone, which can affect its reactivity and handling in chemical reactions.

Chiral reagent

The compound can be used as a chiral reagent, a molecule that can induce chirality (a type of molecular asymmetry) in a chemical reaction, which is important in the synthesis of drugs and other chiral molecules.

Precursor for the synthesis of complex molecules

2,3-bis(4-methoxyphenyl)propanenitrile is used as a precursor, a starting material, for the synthesis of more complex molecules, which is important in the pharmaceutical and agrochemical industries.

Upstream product

• 63785-34-2 (2Z)-2,3-bis(4-methoxyphenyl)prop-2-enenitrile 
• 104-01-8 4-Methoxyphenylacetic acid 
• 32383-67-8 (E)-2,3-bis(4-methoxyphenyl)acrylic acid 
• 93330-31-5 4-Methoxy-α-<4-methoxy-phenyl>-trans-zimtsaeurechlorid 
• 123-11-5 4-methoxy-benzaldehyde 
• 693775-74-5 (E)-2,3-bis(4-methoxyphenyl)acrylamide 
• 2746-25-0 p-Methoxybenzyl bromide 
• 104-47-2 p-methoxybenzylnitrile 
• 6443-74-9 p-methoxy-α-p-methoxyphenylcinnamonitrile 
• 105-13-5 4-Methoxybenzyl alcohol 
• 4705-34-4 4,4'-dimethoxystilbene 
• 77287-34-4 formamide 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 

Downstream Products

• 1428-67-7 2,3-bis-(4-hydroxyphenyl)propionitrile 

Relevant academic research and scientific papers

Nickel/Cobalt-Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent

A Ni/Co co-catalyzed reductive hydrocyanation of various alkynes was developed for the production of saturated nitriles. Hydrocyanic acid is generated in situ from safe and readily available formamide. Formamide played multiple roles as a cyano source, dehydrant, and reductant for the NiII pre-catalyst and vinyl nitriles, along with acting as the co-solvent in this reaction. Detailed mechanistic investigation supported a pathway via hydrocyanation of C≡C bond and the subsequent reduction of C=C bond. Wide substrate scope, the employment of a cheap and stable nickel salt as pre-catalyst, a safe cyano source and convenient experimental operation render this hydrocyanation practical for the laboratory synthesis of saturated nitriles. (Figure presented.).

Synthetic method 2,3 - bis (4 - hydroxyphenyl) propionitrile

2 Is disclosed. 3 - Bis (4 - hydroxyphenyl) propionitrile synthesis method relates to the technical field of electrolyte additives. To the scheme, methoxybenzene acetonitrile is dissolved in an organic solvent,5 - 0 °C of sodium hydride is added,5 - 0 °C

Ni-Catalyzed hydrocyanation of alkenes with formamide as the cyano source

CN generation from formamide dehydration! A novel Ni-catalyzed hydrocyanation of various alkenes to provide aliphatic nitriles is developed by generating hydrocyanic acid in situ from safe and readily available formamide. Excellent linear or branched regio-selectivity, wide substrate scope, cheap and stable nickel salt as a pre-catalyst, a safe cyano source, slow generation of CN to obviate catalyst deactivation and convenient experimental operation would render this hydrocyanation attactive for laboratory synthesis of aliphatic nitriles.

Manganese Catalyzed α-Alkylation of Nitriles with Primary Alcohols

The manganese(I) complex bearing a bidentate hydrazone ligand efficiently catalyzes the α-alkylations of nitrile using primary alcohols as alkylating agents. α-Functionalized nitriles were selectively obtained in good to excellent yields. The reaction is environmentally benign, producing water as the sole byproduct. Both benzylic and aliphatic alcohols could be used and functional groups were tolerated.

ESTROGEN RECEPTOR LIGANDS, COMPOSITIONS AND METHODS RELATED THERETO

Provided are compounds and methods for treating neurodegenerative diseases and conditions, such as multiple sclerosis, using an estrogen receptor-β ligand (ΕΡβ ligand).

Diarylpropionitrile (DPN) enantiomers: Synthesis and evaluation of estrogen receptor β-selective ligands

Two estrogen receptor (ER) subtypes, ERα and ERβ, mediate the actions of estrogens in diverse reproductive and nonreproductive target tissues. ER subtype-selective ligands, which bind to and activate these subtypes differentially, have proved to be useful

Discovery of Diarylacrylonitriles as a Novel Series of Small Molecule Sortase A Inhibitors

On the basis of a hit from random screening, a novel class of small-molecule sortase A inhibitors was generated. The primary structure-activity relationship and the minimal structural requirements for potency were established through structural modifications and molecular modeling studies.

Estrogen receptor-β potency-selective ligands: Structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues

Through an effort to develop novel ligands that have subtype selectivity for the estrogen receptors alpha (ERα) and beta (ERβ), we have found that 2,3-bis(hydroxyphenyl)propionitrile (DPN) acts as an agonist on both ER subtypes, but has a 70-fold higher relative binding affinity and 170-fold higher relative potency in transcription assays with ERβ than with ERα. To investigate the ERβ affinity- and potency-selective character of this DPN further, we prepared a series of DPN analogues in which both the ligand core and the aromatic rings were modified by the repositioning of phenolic hydroxy groups and by the addition of alkyl substituents and nitrile groups. We also prepared other series of DPN analogues in which the nitrile functionality was replaced with acetylene groups or polar functions, to mimic the linear geometry or polarity of the nitrile, respectively. To varying degrees, all of the analogues show preferential binding affinity for ERβ (i.e., they are ERβ affinity-selective), and many, but not all of them, are also more potent in activating transcription through ERβ than through ERα (i.e., they are ERβ potency-selective). meso-2,3-Bis(4-hydroxyphenyl)succinonitrile and dl-2,3-bis(4-hydroxyphenyl)succinonitrile are among the highest ERβ affinity-selective ligands, and they have an ERβ potency selectivity that is equivalent to that of DPN. The acetylene analogues have higher binding affinities but somewhat lower selectivities than their nitrile counterparts. The polar analogues have lower affinities, and only the fluorinated polar analogues have substantial affinity selectivities. This study suggests that, in this series of ligands, the nitrile functionality is critical to ERβ selectivity because it provides the optimal combination of linear geometry and polarity. Furthermore, the addition of a second nitrile group β to the nitrile in DPN or the addition of a methyl substitutent at an ortho position on the β-aromatic ring increases the affinity and selectivity of these compounds for ERβ. These ERβ-selective compounds may prove to be valuable tools in understanding the differences in structure and biological function of ERα and ERβ.