4854-85-7

Usage

Uses

Used in Organic Synthesis:
DMACN is utilized as a reagent in organic synthesis, particularly for the production of pharmaceuticals and agrochemicals. Its unique chemical properties make it a valuable component in the creation of a wide range of compounds.
Used in Pharmaceutical Production:
As a key component in the synthesis of pharmaceuticals, DMACN plays a crucial role in the development of new medications, contributing to advancements in healthcare and medicine.
Used as a Precursor in Organic Compound Synthesis:
DMACN serves as a precursor in the synthesis of various organic compounds, highlighting its importance in the chemical industry and the development of novel substances.
Used as a Stabilizer for Ultraviolet-Curable Resins:
In the field of materials science, DMACN is employed as a stabilizer for ultraviolet-curable resins, enhancing the performance and durability of these materials in various applications.
Used as a Fluorescent Probe in Biochemical Research:
DMACN is also used as a fluorescent probe in biochemical research, aiding scientists in their study of biological processes and the development of new diagnostic tools.
Used in the Development of Luminescent Materials:
Furthermore, DMACN is a building block in the creation of luminescent materials, contributing to the advancement of technology in various fields, such as lighting and display industries.
It is essential to handle DMACN with care, as it is considered harmful if swallowed, inhaled, or absorbed through the skin, and it may cause irritation to the skin and eyes. Proper safety measures should be taken during its use to ensure the well-being of individuals working with (E)-4-(N,N-dimethylamino)cinnamonitrile.

Upstream product

• 372-09-8 cyanoacetic acid 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 50709-87-0 α-benzenesulfonyl-4-dimethylamino-cinnamonitrile 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 97221-11-9 (E)-4-(((4-methoxyphenyl)imino)methyl)-N,N-dimethylaniline 
• 20432-35-3 3-(4-dimethylamino-phenyl)-propenal 
• 75-05-8 acetonitrile 
• 14378-09-7 2-Cyano-3-<4-(N,N-dimethylamino)phenyl>propenoic acid 
• 3252-43-5 dibromoacetonitrile 
• 41463-93-8 4-N,N-dimethylaminobenzaldehyde hydrazone 

Downstream Products

• 290833-00-0 N-{4-[2-(4-dimethylamino-phenyl)-vinyl]-6-isobutyrylamino-[1,3,5]triazin-2-yl}-isobutyramide 
• 1694-45-7 (E)-N,N-dimethyl-4-(2-(pyridin-2-yl)vinyl)aniline 
• 13622-77-0 6-(4-dimethylamino-trans-styryl)-[1,3,5]triazine-2,4-diyldiamine 

Relevant academic research and scientific papers

HCl·DMPU-assisted one-pot and metal-free conversion of aldehydes to nitriles

We report an efficient HCl·DMPU assisted one-pot conversion of aldehydes into nitriles. The use of HCl·DMPU as both an acidic source as well as a non-nucleophilic base constitutes an environmentally mild alternative for the preparation of nitriles. Our protocol proceeds smoothly without the use of toxic reagents and metal catalysts. Diverse functionalized aromatic, aliphatic and allylic aldehydes incorporating various functional groups were successfully converted to nitriles in excellent to quantitative yields. This protocol is characterized by a broad substrate scope, mild reaction conditions, and high scalability. This journal is

Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy

Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.

Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1)

5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type 1 receptor (CB1). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CB1: a critical chain length at the C3-position, an electron withdrawing group at the C5-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B these significantly impact the binding affinity (KB) and the binding cooperativity (α). A potent CB1 allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-propyl-1H-indole- 2-carboxamide (12d) was identified. It exhibited a KB of 259.3 nM with a strikingly high binding α of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (12f) with a KB of 89.1 nM, which is among the lowest KB values obtained for any allosteric modulator of CB1 these positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced β-arrestin mediated ERK1/2 phosphorylation.

A new method for the synthesis of cinnamonitriles by catalytic olefination

Catalytic olefination of hydrazones of aromatic aldehydes with dibromoacetonitrile affords cinnamonitriles.

Pathways for the solvent-free condensation between schiff bases and methylenic compounds

Pathways for the solvent-free condensation between Schiff Bases and methylenic compounds are discussed taking into account the reported mechanistic purposes and new experimental data.

Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 1: The search for alkenyl-DPPs. Unsaturated nitriles in standard DPP syntheses: A novel cyclopenta[c]pyrrolone chromophore

Reactions of the anion of ethyl 4,5-dihydro-5-oxo-2-phenylpyrrole-3-carboxylate with the Diels-Alder adducts of acrylonitrile and various dienes rarely yield the expected DPP derivatives. The reaction with cyclohex-3-enecarbonitrile provides a noteworthy exception: thermolysis of the resulting cyclohexenyl-DPP gives butadiene and impure 3-ethenyl-6-phenyl-DPP, the latter being thermally unstable. Michael additions predominate when the above anion reacts with α,β-unsaturated nitriles: acrylonitrile and methacrylonitrile give 4,4-bis(cyanoethyl) and 4,4-bis(2-cyanopropyl) derivatives, and cinnamonitrile, substituted cinnamonitriles and 3-(2-thienyl)acrylonitrile give deep red 3-aryl-5-cyano-4-hydroxy-2H-cyclopenta[c]pyrrol-1-ones. These ambident nucleophiles may undergo N- and either O- or C-alkylation according to the alkylating agent used.

Stereoselective Synthesis of (E)-Cinnamonitriles with the SmI2/THF/MeOH System

α-Phenylsulfonylcinnamonitriles are readily reduced by SmI2/THF/MeOH to give the corresponding (E)-cinnamonitriles in good yields under mild conditions.

Transmission of substituent effects through extended systems-I. p-Substituted cinnamonitriles

Infrared data, 13C chemical shifts and ab-initio calculations are reported for a series of p-substituted cinnamonitriles.The i.r. values include intensities for the benzene, ethylene and cyanide vibrations which allow an estimation of resonance effects.The relative importance of the various mechanisms of transmission of electronic effects are discussed.