4854-85-7

Basic information

• Product Name: (E)-4-(N,N-dimethylamino)cinnamonitrile
• Synonyms: (E)-4-(N,N-dimethylamino)cinnamonitrile
• CAS NO: 4854-85-7
• Molecular Weight: 172.23
• Mol File: 4854-85-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (E)-4-(N,N-dimethylamino)cinnamonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(N,N-dimethylamino)cinnamonitrile(4854-85-7)
• EPA Substance Registry System: (E)-4-(N,N-dimethylamino)cinnamonitrile(4854-85-7)

Safety Data

• Hazardous Substances Data: 4854-85-7(Hazardous Substances Data)

Usage

Description

(E)-4-(N,N-dimethylamino)cinnamonitrile, also known as DMACN, is a chemical compound characterized by its yellowish to brownish liquid appearance and a faint amine odor. With the molecular formula C12H14N2, it exhibits insolubility in water but is soluble in organic solvents. (E)-4-(N,N-dimethylamino)cinnamonitrile is recognized for its versatile applications in various industries, including organic synthesis, pharmaceuticals, and materials science.

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 this compound.

Upstream product

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

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 articles and documents

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

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.

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.