269-12-5

Basic information

• Product Name: 1H-naphtho(2,3-d)triazole
• Synonyms: 1H-naphtho(2,3-d)triazole;1(H)-Naphthotriazol;2H-benzo[f]benzotriazole
• CAS NO: 269-12-5
• Molecular Formula: C₁₀H₇N₃
• Molecular Weight: 169.18
• Mol File: 269-12-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 187 °C
• Boiling Point: 392.8°Cat760mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.381g/cm³
• Vapor Pressure: 2.23E-06mmHg at 25°C
• Refractive Index: 1.804
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.38±0.30(Predicted)
• CAS DataBase Reference: 1H-naphtho(2,3-d)triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-naphtho(2,3-d)triazole(269-12-5)
• EPA Substance Registry System: 1H-naphtho(2,3-d)triazole(269-12-5)

Safety Data

• Hazardous Substances Data: 269-12-5(Hazardous Substances Data)

Usage

Description

1H-naphtho(2,3-d)triazole is an organic compound with a unique chemical structure that features a triazole ring fused to a naphthalene backbone. 1H-naphtho(2,3-d)triazole is known for its versatile chemical properties and potential applications in various industries.

Uses

Used in Chemical-Mechanical Polishing (CMP) Industry:
1H-naphtho(2,3-d)triazole is used as an additive in the formation of chemical-mechanical polishing (CMP) fluid for the semiconductor industry. It plays a crucial role in enhancing the planarization process of silicon wafers during the manufacturing of integrated circuits. The compound's ability to interact with the surface of the wafer and the polishing slurry helps achieve a uniform and defect-free surface, which is essential for the performance and reliability of the final product.

InChI:InChI=1/C10H7N3/c1-2-4-8-6-10-9(11-13-12-10)5-7(8)3-1/h1-6H,(H,11,12,13)

Upstream product

• 81903-36-8 2,3-naphthalene bishydrazine 
• 780820-43-1 2-(trimethylsilyl)naphthalen-3-yl trifluoromethanesulfonate 
• 92-44-4 2,3-naphthalenediol 
• 771-97-1 2,3-Diaminonaphthalene 

Downstream Products

• 194417-18-0 1-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-naphtho[2,3-d][1,2,3]triazole 
• 194417-01-1 Methyl 4'-(naphtho[2,3-d][1,2,3]triazol-1-yl)methyl-biphenyl-2-carboxylate 
• 91-59-8 naphthalen-2-ylamine 

Relevant articles and documents

Higher-energy collision-induced dissociation for the quantification by liquid chromatography/tandem ion trap mass spectrometry of nitric oxide metabolites coming from S-nitroso-glutathione in an in vitro model of the intestinal barrier

Rationale: The potency of S-nitrosoglutathione (GSNO) as a nitric oxide (NO) donor to treat cardiovascular diseases (CVDs) has been highlighted in numerous studies. In order to study its bioavailability after oral administration, which represents the most convenient route for the chronic treatment of CVDs, it is essential to develop an analytical method permitting (i) the simultaneous measurement of GSNO metabolites, i.e. nitrite, S-nitrosothiols (RSNOs) and nitrate and (ii) to distinguish them from other sources (endogenous synthesis and diet). Methods: Exogenous GSNO was labeled with 15N, and the GS15NO metabolites after conversion into the nitrite ion were derivatized with 2,3-diaminonaphthalene. The resulting 2,3-naphthotriazole was quantified by liquid chromatography/tandem ion trap mass spectrometry (LC/ITMS/MS) in multiple reaction monitoring mode after Higher-energy Collision-induced Dissociation (HCD). Finally, the validated method was applied to an in vitro model of the intestinal barrier (monolayer of Caco-2 cells) to study GS15NO intestinal permeability. Results: A LC/ITMS/MS method based on an original transition (m/z 171 to 156) for sodium 15N-nitrite, GS15NO and sodium 15N-nitrate measurements was validated, with recoveries of 100.8 ± 3.8, 98.0 ± 2.7 and 104.1 ± 3.3%, respectively. Intra- and inter-day variabilities were below 13.4 and 12.6%, and the limit of quantification reached 5 nM (signal over blank = 4). The permeability of labeled GS15NO (10–100 μM) was evaluated by calculating its apparent permeability coefficient (Papp). Conclusions: A quantitative LC/ITMS/MS method using HCD was developed for the first time to selectively monitor GS15NO metabolites. The assay allowed evaluation of GS15NO intestinal permeability and situated this drug candidate within the middle permeability class according to FDA guidelines. In addition, the present method has opened the perspective of a more fundamental work aiming at studying the fragmentation mechanism leading to the ion at m/z 156 in HCD tandem mass spectrometry in the presence of acetonitrile.

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

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.