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

Uses

1H-naphtho[2,3-d][1,2,3]triazole is used in the formation of chemical-mechanical polishing fluid.

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

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

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.

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.

Crystal-facet-dependent denitrosylation: Modulation of NO release from S-nitrosothiols by Cu2O polymorphs

Nitric oxide (NO), a gaseous small molecule generated by the nitric oxide synthase (NOS) enzymes, plays key roles in signal transduction. The thiol groups present in many proteins and small molecules undergo nitrosylation to form the corresponding S-nitrosothiols. The release of NO from S-nitrosothiols is a key strategy to maintain the NO levels in biological systems. However, the controlled release of NO from the nitrosylated compounds at physiological pH remains a challenge. In this paper, we describe the synthesis and NO releasing ability of Cu2O nanomaterials and provide the first experimental evidence that the nanocrystals having different crystal facets within the same crystal system exhibit different activities toward S-nitrosothiols. We used various imaging techniques and time-dependent spectroscopic measurements to understand the nature of catalytically active species involved in the surface reactions. The denitrosylation reactions by Cu2O can be carried out multiple times without affecting the catalytic activity.