2393-18-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Aminocinnamic acid is used as a key intermediate in the synthesis of various pharmaceuticals due to its ability to facilitate the creation of new drug molecules. Its presence in the molecular structure can enhance the pharmacological properties of the resulting compounds, making it an essential component in drug development.
Used in Organic Chemistry:
As a versatile building block, 4-Aminocinnamic acid is used in organic chemistry for the synthesis of a range of organic compounds. Its reactivity and structural features allow for the formation of diverse chemical entities, contributing to the advancement of organic synthesis techniques and the discovery of new chemical products.
Used in Dye Production:
4-Aminocinnamic acid is utilized as a precursor in the production of dyes. Its chemical properties enable the creation of dyes with specific color characteristics and stability, which are important in various applications such as textiles, printing, and other industries that rely on colorants.
Used in Agriculture:
In the agricultural sector, 4-Aminocinnamic acid finds use in the development of agrochemicals. Its potential to be incorporated into compounds that can enhance crop protection or stimulate plant growth makes it a valuable asset in agricultural research and product development.
Used in Material Science:
4-Aminocinnamic acid is employed in material science for the development of new materials with specific properties. Its integration into material compositions can lead to advancements in areas such as polymer science, where it may contribute to the creation of materials with improved mechanical, thermal, or electrical properties.

Upstream product

• 619-89-6 p-nitrocinnamic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 209344-13-8 4-nitrophenylacrylic acid tert-butyl ester 
• 79-10-7 acrylic acid 
• 106-40-1 4-bromo-aniline 
• 2033-24-1 cycl-isopropylidene malonate 
• 556-18-3 4-aminobenzaldehyde 
• 2922-41-0 (p-aminophenyl)alanine 
• 621-82-9 Cinnamic acid 
• 943-80-6 4-amino-L-phenylalanine 
• 105-53-3 diethyl malonate 
• 162936-33-6 4-aminocinnamic acid tert-butyl ester 
• 7647-01-0 hydrogenchloride 
• 953-26-4 ethyl 4-nitrocinnamate 

Downstream Products

• 1615-02-7 p-chlorocinnamic acid 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 34633-09-5 3-(p-iodophenyl)acrylic acid 
• 2393-17-1 3-(4-aminophenyl)propionic acid 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 116557-37-0 4-benzamino-trans-cinnamic acid 
• 67249-02-9 4-acetoaminocinnamic acid 
• 934473-89-9 C₂₈H₄₅N₅O₆ 
• 1091595-69-5 p-(9-fluorenylmethoxycarbonylamino)-cinnamic acid 
• 1562416-89-0 4,4'-diamino-α-truxillic acid dimethyl ester 
• 1562417-20-2 4,4'-diamino-α-truxillic acid diethyl ester 
• 461461-89-2 4-aminocinnamyl alcohol 
• 621-95-4 4,4'-diaminodihydrostilbene 
• 33267-39-9 N,N'-diacetyl-4,4'-diaminostilbene 

Relevant academic research and scientific papers

Ultrahigh performance bio-based polyimides from 4,4′-diaminostilbene

We have developed a novel route for the synthesis of high-performance bio-polyimides (PIs) microbially-derived from photo-responsive aromatic diamine 4,4′-diaminostilbene (DAS) and its reduced counterpart 4, 4′-(ethane-1,2-diyl)dianiline (EDDA). DAS and EDDA were condensed with various commercially-available dianhydrides to obtain a series of poly(amic acid)s (PAAs) and PIs which were characterized in terms of their thermal, mechanical, and photo-functions. These bio-based PAAs showed a very high viscosity of 6.62 dL/g, and the PIs showed ultrahigh thermal resistance with Td10 values over 600 °C, which were higher than that of any bio-based plastic reported thus far. They also showed Tg values above 250 °C, and tensile strength of over 132 MPa, which is higher than that of Kapton. The PIs also showed photo-functional behavior based on stilbene-based photoreactions.

Synthesis and characterization of bifunctional lipophilic and basic mesoporous organosilica supported palladium nanoparticles as an efficient and ecofriendly nanocomposite in aqueous Heck reaction

In the present study, a highly ordered mesoporous organosilica nanocomposite having modified pore channels with both lipophilic and basic units, SBA-R/Im-NH2, was synthesized through surfactant-templated sol-gel methodology and post modification process. The nanocomposite with ionic liquid properties was used as a potential host for supporting palladium nanoparticles. The structure and composition of the target nanocomposite, SBA-R/Im-NH2·Pd, were supported by infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), elemental analysis (CHNS), energy dispersive X-ray (EDX) and Brunauer-Emmett-Teller (BET) measurements. The efficiency of this porous inorganic-organic hybrid nanocomposite as a powerful catalyst in one of the most important carbon-carbon bond-forming process, the Heck coupling reaction of aryl halides with olefins, in aqueous media was also examined. This method has the advantages of high yields, cleaner reactions, simple methodology, short reaction times, easy workup, and greener conditions. In addition, the nanocatalyst can be easily separated from the reaction mixture and reused several times without significant decrease in activity and promises economic as well as environmental benefits.

A green chemical synthesis of coumarin-3-carboxylic and cinnamic acids using crop-derived products and waste waters as solvents

Crop-derived products, like juices obtained from edible fruits and vegetables, and waste waters deriving from agricultural and industrial processing have been recently exploited to efficiently promote several ‘classic’ and innovative synthetic organic reactions. Such a green chemical approach prevented the use of toxic, polluting, and hazardous materials and in the mean time allowed to increase the commercial values of crop products and industrial byproducts. Coumarin-3-carboxylic and cinnamic acids represent classes of naturally occurring and semi-synthetic compounds with interesting and promising pharmacological activities. In this Letter a new and improved methodology for the Knoevenagel condensation yielding the title compounds using juices from edible fruits and vegetables (lemon, grapefruit, carrot, pomegranate, kiwi, vinegar, tomato), liqueurs (limoncello), and waste waters (buttermilk and residues of olive processing) as solvents is described. Coumarin-3-carboxylic and cinnamic acids have been synthesized in excellent yields by ultrasound irradiation from differently substituted 2-hydroxybenzaldehydes, 2-hydroxyacetophenones, and benzaldehydes, and Meldrum's acid as starting substrates. The findings described herein enforce the concept of the usefulness of products and byproducts derived from agriculture and food industry to accomplish green chemical processes.

Biobased polyimides from 4-aminocinnamic acid photodimer

The development of high-performance biobased polymers such as polyimides (PIs) is indispensable to establish a sustainable green society, but it is very difficult due to the incompatibility of their monomeric aromatic diamines with microorganisms. Here, we developed biobased PIs from bioavailable aromatic diamines, which were photodimers of 4-aminocinnamic acid (4ACA) derived from genetically manipulated Escherichia coli. These biobased PI films showed ultrahigh thermal resistance with T10 values over 425 °C and no Tg values under 350 °C, which is the highest value of all biobased plastics reported thus far. The PI films also showed high tensile strength, high Young's moduli, good cell compatibility, excellent transparency, and high refractive indices.

Selective reduction of nitro compounds using CeY zeolite under microwaves

Aliphatic and aromatic nitro compounds were selectively reduced to their corresponding amino derivatives in good yields using formic acid and CeY zeolite under monomode reactor. This system is found to be compatible with several sensitive functionalities. Beside the recycling result showed it had a long catalyst lifetime and could maintain activity even after being used for 20 cycles.

A facile method for synthesis of amine-functionalized mesoporous zirconia and its catalytic evaluation in Knoevenagel condensation

Amine-functionalized mesoporous zirconia was prepared by a co-condensation method using silane (aminopropyltrimethoxysilane, APTES) and zirconium butoxide. The materials were characterized by X-ray diffraction, BET surface area analysis, 13C magic angle spinning-nuclear magnetic resonance (NMR), Fourier-transfer infrared spectroscopy (FTIR), transmittance electron micrography (TEM), and CHN analysis. FTIR and NMR results revealed the successful grafting of organic amines onto the surface of zirconia. The catalytic activities were investigated for liquid phase Knoevenagel condensation of various aromatic aldehydes with diethyl malonate. The catalysts showed excellent yield of products at room temperature in solvent-free condition.

A new reagent for selective reduction of nitro group

The nitro group in aromatic nitro compounds containing reducible substitucnts such as methyl, carboxylic acids and phcnols, and halogcns arc selectively and rapidly reduced at room temperature to the corresponding amines in good yield by employing hydrazine glyoxylatc in the presence of zinc powder or magnesium powder. It has been observed that hydrazine glyoxylatc is more effective than hydrazine, glyoxylic acid, hydrazinium monoformate or ammonium monoformate and reduction of the nitro group occurs without hydrogcnolysis in the presence of low-cost magnesium compared to expensive metals like palladium, platinum, ruthenium, etc. The products have been characterized by comparison of their TLC, infrared spectra and melting points.

CINNAMOYL INHIBITORS OF TRANSGLUTAMINASE

A compound of Formula, (I) or Formula: (II)

Zinc/ammonium formate: A new facile system for the rapid and selective reduction of oximes to amines

Various oximes, both aldoximes and ketoximes, are selectively reduced to corresponding amines employing low cost zinc dust and ammonium formate despite presence of other functional groups such as halogens, -OH, -OCH3, -COOH, -CN, > C = C 3.

Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds

The nitro group in aliphatic and aromatic nitro compounds also containing reducible substituents such as ethene, nitrile, carboxylic acid, phenol, halogen, ester etc., are selectively and rapidly reduced at room temperature to corresponding amines in good yields by employing 99-100% hydrazine hydrate, in the presence of commercial zinc dust. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.