18664-39-6

Basic information

• Product Name: 4-Cyanocinnamic acid
• Synonyms: 3-(4-CYANOPHENYL)ACRYLIC ACID;AKOS BAR-2475;4-CYANOCINNAMIC ACID;RARECHEM BK HD C008;cyanocinnamicacid;p-cyanocinnamic acid;3-(4-Cyanophenyl)propenoic acid;3-(4-cyanophenyl)acrylic acid (en)
• CAS NO: 18664-39-6
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.17
• EINECS: 242-484-8
• Mol File: 18664-39-6.mol
• Article Data: 48

Chemical Properties

• Melting Point: 245-248°C
• Boiling Point: 380.4 °C at 760 mmHg
• Flash Point: 183.9 °C
• Appearance: /
• Density: 1.26 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.13±0.10(Predicted)
• CAS DataBase Reference: 4-Cyanocinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyanocinnamic acid(18664-39-6)
• EPA Substance Registry System: 4-Cyanocinnamic acid(18664-39-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 18664-39-6(Hazardous Substances Data)

Usage

General Description

4-Cyanocinnamic acid is a chemical compound with the molecular formula C10H7NO2. It is a white to off-white crystalline powder that is sparingly soluble in water. 4-Cyanocinnamic acid is primarily used as an intermediate in the production of pharmaceuticals, dyes, and other organic compounds. It is also used in the synthesis of various esters and aromatic compounds. Its chemical structure makes it an important building block in organic chemistry, and it has a wide range of potential applications in research and industry. Additionally, 4-Cyanocinnamic acid has demonstrated potential bioactive properties that make it of interest in the development of new drugs and biologically active compounds.

Upstream product

• 127-08-2 potassium acetate 
• 108-24-7 acetic anhydride 
• 105-07-7 4-cyanobenzaldehyde 
• 141-82-2 malonic acid 
• 3058-39-7 4-iodobenzonitrile 
• 105-53-3 diethyl malonate 
• 79-10-7 acrylic acid 
• 623-00-7 4-bromobenzenecarbonitrile 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 133430-47-4 p-nitrobenzyl 4-cyanocinnamate 
• 110-89-4 piperidine 
• 3375-31-3 palladium diacetate 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 20655-58-7 ethyl (E)-4-cyanocinnamate 

Downstream Products

• 97190-62-0 (E)-4-cyanocinnamoyl chloride 
• 879407-23-5 4'-bromo-2'-methyl-cis-stilbene-carbonitrile-⁽⁴⁾ 
• 52116-83-3 methyl 3‐(4‐cyanophenyl)acrylate 
• 138611-01-5 (1R,2S,3R,4S)-3,4-Bis-(4-cyano-phenyl)-cyclobutane-1,2-dicarboxylic acid 
• 66516-96-9 C₁₀H₈N₂O 
• 83101-12-6 4-(3-Hydroxypropyl)benzonitrile 
• 3032-92-6 4-cyanophenylacetylene 
• 60592-58-7 (Z)-4-(2-bromovinyl)benzonitrile 
• 157518-33-7 4-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile 
• 107605-78-7 6-(4-cyanobenzyl)-1,4,7-trimethyl-5,8-dioxo-1,4,5,6,7,8-hexahydroimidazo<4,5-e><1,4>diazepine 

Relevant articles and documents

Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)

Cinnamic acid derivatives (CAD's) represent a great alternative in the search for insecticides against Aedes aegypti mosquitoes since they have antimicrobial and insecticide properties. Ae. aegypti is responsible for transmitting Dengue, Chikungunya, and Zika viruses, among other arboviruses associated with morbimortality, especially in developing countries. In view of this, in vitro analyses of n-substituted cinnamic acids and esters were performed upon 4th instar larvae (L4) of Ae. aegypti, as well as, molecular docking studies to propose a potential biological target towards this mosquitoes species. The larvicide assays proved that n-substituted ethyl cinnamates showed a more pronounced activity than their corresponding acids, in which p-chlorocinnamate (3j) presented a LC50 value of 8.3 μg/mL. Thusly, external morphologic alterations (rigid and elongated body, curved bowel, and translucent or darkened anal papillae) of mosquitoes’ group exposed to compound 3j, were observed by microscopy. In addition, an analytical method was developed for the quantification of the most promising analog by using high-performance liquid chromatography with UV detection (HPLC-UV). Molecular docking studies suggested that the larvicide action is associated with inhibition of acetylcholinesterase (AChE) enzyme. Therefore, expanding the larvicidal study with the cinnamic acid derivatives against the vector Ae. aegypti is important for finding search for more effective larvicides and with lower toxicity, since they have already shown good larvicidal properties against Ae. aegypti.

Phenanthroline functionalized polyacrylonitrile fiber with Pd(0) nanoparticles as a highly active catalyst for the Heck reaction

A series of polyacrylonitrile fibers (PANF) functionalized with nitrogen-containing ligands were prepared and then used to synthesize fiber-supported Pd(0) nanoparticle catalysts. The phenanthroline-functionalized PANF with immobilized Pd(0) nanoparticles (PANPhenF-Pd(0)) had the best catalytic activity for the Heck reaction under solvent-free conditions. The PANPhenF-Pd(0) efficiently stabilized the nanoparticles and they were well-dispersed with Pd(0) particle sizes of about 3 nm. The PANPhenF-Pd(0) structure was further characterized by a variety of instrumental methods. A probable mechanism based on the fiber's microenvironment is proposed for the Heck reaction catalyzed by PANPhenF-Pd(0). The PANPhenF-Pd(0) catalyst is easily recovered from the reaction system and can be used up to six times with only a slight decrease in catalytic activity and with low Pd leaching. The PANPhenF-Pd(0) catalyst also has excellent catalytic activity for gram-scale use.

New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation

Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.