35086-82-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorocinnamoyl chloride is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its reactivity allows for the creation of new compounds with potential medicinal properties, contributing to the development of novel treatments and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chlorocinnamoyl chloride serves as a building block in the production of agrochemicals. Its involvement in the synthesis of these compounds helps in the development of effective pesticides, herbicides, and other agricultural products that protect crops and enhance yield.
Used in Dye and Pigment Industry:
2-Chlorocinnamoyl chloride is utilized as a chemical intermediate in the synthesis of dyes and pigments. Its reactive nature facilitates the creation of a wide range of colorants used in various applications, including textiles, plastics, and printing inks.
Used in Fragrance Industry:
2-CHLOROCINNAMOYL CHLORIDE is also employed in the fragrance industry, where it acts as a precursor in the production of various scented compounds. Its role in the synthesis process helps in creating unique and complex fragrances for use in perfumes, cosmetics, and other scented products.
Used in Polymer Industry:
2-Chlorocinnamoyl chloride is used as a building block in the synthesis of polymers. Its reactivity contributes to the development of new polymeric materials with specific properties, such as improved strength, flexibility, or chemical resistance, for use in various industries.
Safety Precautions:
Due to its highly reactive nature and potential to cause skin and eye irritation, 2-chlorocinnamoyl chloride should be handled with care. It is essential to follow appropriate safety guidelines and regulations for its storage and use to minimize risks and ensure the safety of personnel and the environment.

InChI:InChI=1/C9H6Cl2O/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6H/b6-5+

Upstream product

• 3752-25-8 o-chlorocinnamic acid 

Downstream Products

• 56140-30-8 2-chloro-cinnamic acid anilide 
• 1092480-03-9 N-{7-[(2E)-3-(2-chlorophenyl)prop-2-enoyl]-2,3-dimethylimidazo[1,2-a]pyridin-8-yl}-2,2-dimethylpropanamide 
• 1186073-49-3 (E)-3-(2-chlorophenyl)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)acrylamide 
• 349423-35-4 N-(phenyl)-N-methyl-2-chlorocinnamamide 
• 1613220-29-3 C₂₄H₂₇ClN₂O₃ 
• 24393-51-9 ethyl 3-(2-chlorophenyl)acrylate 
• 1637568-89-8 C₁₈H₁₇ClO₅ 
• 859505-63-8 C₁₅H₉ClO₅ 

Relevant academic research and scientific papers

N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites

The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.

1,4-Palladium Shift/C(sp3)-H Activation Strategy for the Remote Construction of Five-Membered Rings

1,n-Metal shift is an elegant alternative approach enabling the functionalization of remote C-H bonds from simple precursors. In this work, we report a novel and simple Pd0-catalyzed domino reaction involving 1,4-palladium shift and C(sp3)-H activation and leading to (fused) five-membered rings. This method allowed access to a broad range of valuable arylidene γ-lactams and indanones and was applied to the formal synthesis of (-)-pyrrolam.

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection

A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.

Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines

A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).

UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions

UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.

A novel direct synthesis of 3-acyl-4-aryldihydroquinolin-2(1H)-ones via metal-free radical tandem cyclization between N-arylcinnamamides and aldehydes

An efficient metal-free and practical method for the synthesis of disubstituted dihydroquinolin-2(1H)-ones via intermolecular radical tandem addition/cyclization was developed. This method provides a novel and straightforward route to 3-acyl-4-aryldihydro

Silver-catalyzed radical tandem cyclization for the synthesis of 3,4-disubstituted dihydroquinolin-2(1 H)-ones

A silver-catalyzed tandem decarboxylative radical addition/cyclization of N-arylcinnamamides with aliphatic carboxylic acids is reported. This method affords a novel and straightforward route to various 3,4-disubstituted dihydroquinolin-2(1H)-ones in aque

Synthesis and anti-influenza activities of novel baicalein analogs

A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0-4.5 μM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC 50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.

The synthesis of 3,4-disubstituted dihydroquinolin-2(1H)-one under metal-free conditions in aqueous solution

A novel route toward 3,4-disubstituted dihydroquinolin-2(1H )-ones via radical process has been developed in aqueous solution without metals. This method offers a new and simple route for the synthesis of skeleton of dihydroquinolin-2(1H )-one in one step

Silver-catalyzed radical tandem cyclization: An approach to direct synthesis of 3-acyl-4-arylquinolin-2(1 H)-ones

A silver-catalyzed efficient and practical synthesis of 3-acyl-4-arylquinolin-2(1H)-ones or 3-acyl-4-aryldihydroquinolin-2(1H)-ones through intermolecular radical addition/cyclization in aqueous solution is reported. This method provides a novel, highly e