328012-09-5

Basic information

• Product Name: 1-cinnamoyl-1H-1,2,3-benzotriazole
• Synonyms: 1-cinnamoyl-1H-1,2,3-benzotriazole
• CAS NO: 328012-09-5
• Molecular Formula: C₁₅H₁₁N₃O
• Molecular Weight: 249.26734
• Mol File: 328012-09-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-cinnamoyl-1H-1,2,3-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cinnamoyl-1H-1,2,3-benzotriazole(328012-09-5)
• EPA Substance Registry System: 1-cinnamoyl-1H-1,2,3-benzotriazole(328012-09-5)

Safety Data

• Hazardous Substances Data: 328012-09-5(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
1-cinnamoyl-1H-1,2,3-benzotriazole is used as a photostabilizer and UV absorber for protecting plastics from degradation caused by exposure to ultraviolet radiation. It absorbs UV light and dissipates the energy as heat, preventing damage to the plastic material.
Used in Coatings Industry:
1-cinnamoyl-1H-1,2,3-benzotriazole is used as a photostabilizer and UV absorber in coatings to protect them from degradation caused by exposure to ultraviolet radiation. It helps in increasing the lifespan and durability of coated products, especially those used in outdoor applications.
Used in Adhesives Industry:
1-cinnamoyl-1H-1,2,3-benzotriazole is used as a photostabilizer and UV absorber in adhesives to protect them from degradation caused by exposure to ultraviolet radiation. It ensures the longevity and performance of adhesive-based products, particularly those used in outdoor applications.
Used as an Antioxidant:
1-cinnamoyl-1H-1,2,3-benzotriazole is used for its antioxidant properties, making it useful in the protection of various materials from oxidative degradation. It helps in maintaining the stability and performance of materials over time.

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 621-82-9 Cinnamic acid 
• 102-92-1 Cinnamoyl chloride 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 2592-95-2 benzotriazol-1-ol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 37073-15-7 1-(methanesulfonyl)-1H-1,2,3-benzotriazole 
• 201230-82-2 carbon monoxide 
• 100-52-7 benzaldehyde 

Downstream Products

• 1615-22-1 2-(2-phenylethenyl)-4,5-dihydro-4,4-dimethyl-1,3-oxazole 
• 857248-74-9 2,2-dimethyl-6-[(E)-2-oxo-4-phenyl-3-butenyl]-4H-1,3-dioxin-4-one 
• 6876-68-2 N-(4-methylphenyl)-3-phenyl-2-propenamide 
• 58369-45-2 (E)-1,5-diphenylpent-4-ene-1,3-dione 
• 57152-94-0 N-benzylcinnamamide 
• 16619-19-5 N-morpholinocinnamide 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1042416-37-4 3-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenyl-N-p-tolylpropanamide 
• 881901-96-8 3-(1H-benzo[d][1,2,3]triazol-1-yl)-N-(4-chlorophenyl)-3-phenylpropanamide 
• 1042416-43-2 C₂₂H₂₀N₄O₂ 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 
• 881901-87-7 3-(1H-benzo[d][1,2,3]triazol-1-yl)-N,3-diphenylpropanamide 
• 1042416-40-9 3-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenyl-N-m-tolylpropanamide 
• 1052108-53-8 C₁₈H₁₆O₂S 

Relevant articles and documents

Hypervalent iodine in synthesis. 65: A new route to synthesize N-acylbenzotriazoles via palladium catalyzed carbonylation of benzotriazole and hypervalent iodonium salts in the presence of carbon monoxide

N-acylbenzotriazoles are obtained directly in fair yields by palladium-catalyzed carbonylation of diaryliodonium salts with benzotriazoles in the presence of carbon monoxide.

Methods for preparing amide compounds using alkynes and methods for preparing peptides using the same

The present invention relates to a method for preparing an amide compound, which comprises a step of agitating an alkyne and an N-hydroxy compound in an organic solvent in the presence of a transition metal catalyst to form an amide bond, and a method for preparing a peptide using the same. According to the present invention, the amidation reaction does not depend on polar reactivity, such as the conventional simple nucleophilicity and electrophilicity, but is based on a reaction derived from coordination reactivity between an alkyne and a transition metal, and thus shows excellent chemical selectivity. In addition, the method does not require a consumptive step such as attachment and detachment of a protecting group but includes a simple process during the synthesis of a peptide. Thus, the method is very effective for preparing a polypeptide compound. The method also has 100% of atomic economic efficiency since the starting materials are not lost during the reaction.COPYRIGHT KIPO 2017

An efficient one-pot synthesis of: N, N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles

A facile and high-yielding one-pot synthesis of carbamates and N,N′-disubstituted symmetrical ureas from N-acylbenzotriazoles has been devised. It is believed that, the intermediate acyl-azide undergo Curtius rearrangement and in different solvents gives different products i.e. carbamates in alcohols and N,N′-disubstituted symmetrical urea in THF.

Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents

A series of novel quinoline-oxadiazole hybrid compounds was designed based on stepwise rational modification of the lead molecules reported previously, in order to enhance bioactivity and improve druglikeness. The hybrid compounds synthesized were screened for biological activity against Mycobacterium tuberculosis H37Rv and for cytotoxicity in HepG2 cell line. Several of the hits exhibited good to excellent anti-tuberculosis activity and selectivity, especially compounds 12m, 12o and 12p, showed minimum inhibitory concentration values 500. The results of this study open up a promising avenue that may lead to the discovery of a new class of anti-tuberculosis agents.

NEW GUANIDINE DERIVATIVES IN CINNAMIC SERIES

The invention relates to novel guanidine derivatives in the cinnamic series of general formula (I): The invention also relates to the process for preparing said guanidine derivatives and also to synthetic intermediates. Finally, the invention relates to t

Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles

Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles has been achieved by controlling the conditions. Thus, three types of products, namely α,β-unsaturated thioesters, β-thiophenoxy substituted N-acylbenzotriazoles, and β-thiophenoxy substituted thioesters were selectively obtained in good to excellent yields.

Preparation and synthetic applications of N-(α,β-unsaturated acyl)-α-amino acid derivatives

N-(α,β-Unsaturated acyl)-α-amino acids, amides and esters are structural motifs of many biologically active natural products. An alternate and advantageous approach for the synthesis of N-(α,β-unsaturated acyl)-α-amino acid derivatives is developed via ac

Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds

Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3-5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.

Cinnamoyl inhibitors of tissue transglutaminase

(Figure Presented) Transglutaminases (TGases) catalyze the intermolecular cross-linking of certain proteins and tissue TGases (TG2) are involved in diverse biological processes. Unregulated, high TGase activities have been implicated in several physiological disorders, but few reversible inhibitors of TG2 have been reported. Herein, we report the synthesis of a series of novel trans-cinammoyl derivatives, discovered to be potent inhibitors of guinea pig liver transglutaminase. The most effective inhibitors evaluated can be sorted into two subclasses: substituted cinnamoyl benzotriazolyl amides and the 3-(substituted cinnamoyl)pyridines, referred to more commonly as azachalcones. Kinetic evaluation of both of these subclasses revealed that they display reversible inhibition and are competitive with acyl donor TGase substrates at IC50 values as low as 18 μM. An analysis of structure - activity relationships within these series of inhibitors permitted the identification of potentially important binding interactions. Further testing of some of the most potent inhibitors demonstrated their selectivity for TG2 and their potential for further development.

Direct carbon - Carbon bond formation via soft enolization: A facile and efficient synthesis of 1,3-diketones

Ketones undergo soft enolate formation and acylation on treatment with MgBr2·OEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-Pfp esters, and, in these cases, is conducted with untreated, reagent-grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.