1916-72-9

Basic information

• Product Name: 2-PHENYL-2H-BENZOTRIAZOLE
• Synonyms: 2-Phenyl-2H-benzo[d][1,2,3]triazole;2-PHENYL-2H-BENZOTRIAZOLE
• CAS NO: 1916-72-9
• Molecular Formula: C₁₂H₉N₃
• Molecular Weight: 195.21996
• Mol File: 1916-72-9.mol

Chemical Properties

• Melting Point: 106.5-107.5 °C
• Boiling Point: 359.3°Cat760mmHg
• Flash Point: 171.1°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 2.4E-05mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: 2-8°C
• PKA: 1.20±0.30(Predicted)
• CAS DataBase Reference: 2-PHENYL-2H-BENZOTRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-2H-BENZOTRIAZOLE(1916-72-9)
• EPA Substance Registry System: 2-PHENYL-2H-BENZOTRIAZOLE(1916-72-9)

Safety Data

• Hazardous Substances Data: 1916-72-9(Hazardous Substances Data)

Usage

Uses

Used in Plastics and Polymer Industry:
2-PHENYL-2H-BENZOTRIAZOLE is used as a UV stabilizer and absorber for protecting plastics and polymers from degradation caused by ultraviolet light exposure, thereby enhancing their durability and performance.
Used in Coatings and Adhesives Industry:
In the coatings and adhesives industry, 2-PHENYL-2H-BENZOTRIAZOLE is used as a UV stabilizer to prevent the degradation of these materials when exposed to sunlight, maintaining their integrity and functionality over time.
Used in Automotive Parts Production:
2-PHENYL-2H-BENZOTRIAZOLE is utilized as a protective agent in the manufacturing of automotive parts to shield them from the damaging effects of UV radiation, ensuring their longevity and resistance to environmental stress.
Used in Personal Care Products:
In the personal care sector, 2-PHENYL-2H-BENZOTRIAZOLE is used as an active ingredient in sunscreen and skincare products, providing protection against harmful UV radiation, thus contributing to skin health and preventing damage from the sun.
Environmental Considerations:
While 2-PHENYL-2H-BENZOTRIAZOLE offers significant benefits in various industries, it has been identified as persistent in the environment. Its detection in water bodies, soil, and aquatic organisms has raised concerns regarding its potential ecological and human health impacts, necessitating careful management and consideration of alternative or supplementary protective measures.

InChI:InChI=1/C12H9N3/c1-2-6-10(7-3-1)15-13-11-8-4-5-9-12(11)14-15/h1-9H

Upstream product

• 98-95-3 nitrobenzene 
• 95-54-5 1,2-diamino-benzene 
• 2835-58-7 2-aminoazobenzene 
• 72602-70-1 4-(2-nitrophenyl)-3-phenyl-1,2,4-oxadiazol-5-one 
• 99137-20-9 N²-(2,4,6-triphenylpyridinio)-N¹-(2-nitrophenyl)benzamidinide 
• 95-14-7 1,2,3-Benzotriazole 
• 591-50-4 iodobenzene 
• 21819-66-9 2-phenyl-2H-benzo[d][1,2,3]triazol-5-amine 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 51750-18-6 2-phenyl-2H-benzotriazole 1-oxide 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 29530-39-0 1-(2-nitrobenzene)-2-phenyldiazene 

Downstream Products

• 22300-57-8 2-phenyl-1,2,3-triazole-4,5-dicarboxylic acid 
• 122652-16-8 dimethyl 2-phenyl-2H-1,2,3-triazole-4,5-dicarboxylate 
• 35142-82-6 2-phenyl-2H-benzotriazole-4,7-dione 
• 62-53-3 aniline 
• 95-54-5 1,2-diamino-benzene 
• 883741-49-9 4,7-dibromo-2-phenyl-2H-benzo[d][1,2,3]triazole 
• 40756-56-7 2-(2-methoxyphenyl)-2H-benzo[d][1,2,3]triazole 
• 1616057-73-8 2-(2-isopropoxyphenyl)-2H-benzo[d][1,2,3]triazole 
• 1610769-06-6 2-(3',5'-dimethylbiphenyl-2-yl)-2H-benzo[d][1,2,3]triazole 
• 1610769-08-8 methyl 2'-(2H-benzo[d][1,2,3]triazol-2-yl)biphenyl-4-carboxylate 
• 1610769-07-7 2-(4'-methoxybiphenyl-2-yl)-2H-benzo[d][1,2,3]triazole 
• 51776-70-6 2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole 
• 72674-90-9 2-phenyl-4,5,6,7-tetrahydro-2H-benzo-1,2,3-triazole 

Relevant articles and documents

Selective and Scalable Electrosynthesis of 2H-2-(Aryl)-benzo[d]-1,2,3-triazoles and Their N-Oxides by Using Leaded Bronze Cathodes

Electrosynthesis of 2H-2-(aryl)benzo[d]-1,2,3-triazoles and their N-oxides from 2-nitroazobenzene derivatives is reported. The electrolysis is conducted in a very simple undivided cell under constant current conditions with a leaded bronze cathode and a g

Cu(I)/KOH-Promoted Condensation between o-Arylenediamines and Nitroarenes to Access 2-Aryl-2H-Benzotriazoles

Reported is the condensation between o-arylenediamines and nitroarenes enabled by a cooperative action of acid and base, providing a direct entry to 2-aryl-2H-benzotriazoles. The potential practicability of this methodology was demonstrated by 100 mmol-scale reactions and the synthesis of serotonin/dopamine receptor ligand and human growth hormone. (Figure presented.).

Selective Synthesis of N-H and N-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes

The synthetic utility of NaN3 as the azide component in the [3 + 2] annulation with arynes generated from 2-(trimethylsilyl)aryltriflates resulting in the transition-metal-free synthesis of N-H and N-aryl benzotriazoles has been demonstrated. Using CsF as the fluoride source in CH3CN, the N-H benzotriazoles are formed in high selectivity instead of the expected azidobenzene. Interestingly, N-aryl benzotriazoles are formed using KF and THF as solvent in an open-flask reaction. Moreover, a method for the N1-arylation of benzotriazole is also presented.

Catalyst-Free Regioselective N2 Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts

The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.

Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis

The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.

Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide

A new approach for highly regioselective iodination of azobenzenes with alkyl iodide as the iodinating reagent enabled by Rh-catalyzed oxidative C-H activation has been developed. By changing the oxidant, various mono- and di-iodinated azobenzenes were smoothly obtained in moderate to excellent yields, respectively. The preliminary mechanistic study reveals that the reaction process might undergo electrophilic substitution of the directed ortho metalated five-membered rhodacycle compound by an iodine cationic species generated in situ from alkyl iodide and oxidant.

Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds

Modification of benzotriazoles with iodonium salts [diphenyl- and (E)-styrylphenyliodonium tosylates] occurs at the N1-position in the presence of K2CO3 as a base and CuI as a catalyst in CH2Cl2, wher

A Highly Selective Amidation of Azoxybenzenes with Sulfonamides via Rhodium(III)-Catalyzed C-H Activation

A new amidation of azoxybenzenes with sulfonamides catalyzed by a rhodium(III) salt has been developed. This sulfonamidation proceeds efficiently under mild reaction conditions to generate new C-N bonds through C-H bond activation and functionalization, affording the corresponding 2-sulfonamidoazoxybenzenes in good yields with high regioselectivity.

A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV = O Redox Cycling

A small-ring phosphacycle, 1,2,2,3,4,4-hexamethylphosphetane, is found to catalyze deoxygenative N-N bond-forming Cadogan heterocyclization of o-nitrobenzaldimines, o-nitroazobenzenes, and related substrates in the presence of hydrosilane terminal reductant. The reaction provides a chemoselective catalytic synthesis of 2H-indazoles, 2H-benzotriazoles, and related fused heterocyclic systems with good functional group compatibility. On the basis of both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV = O cycling, where DFT modeling suggests a turnover-limiting (3+1) cheletropic addition between the phosphetane catalyst and nitroarene substrate. Strain/distortion analysis of the (3+1) transition structure highlights the controlling role of frontier orbital effects underpinning the catalytic performance of the phosphetane.

AgNO3 as nitrogen source for rhodium(III)-catalyzed synthesis of 2-aryl-2H -benzotriazoles from azobenzenes

A new approach has been established for Rh(iii)-catalyzed direct aza oxidative cyclization of non-prefunctionalized azobenzenes to provide 2-aryl-2H-benzotriazoles in good yields, in which AgNO3 instead of conventional azide reagents for the first time functions as the nitrogen source for the nitrogenation reaction. Preliminary mechanistic studies suggest that the Rh(iii)-catalyst could account for the nitration reaction, and subsequently cationic silver species might both play a vital role in the fission of the nitrogen-oxygen bonds in nitro groups and promote aza oxidative cyclization.