1975-39-9

Basic information

• Product Name: 1-phenyl-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanobenzotriazole
• Synonyms: 1-phenyl-3a,4,5,6,7,7a-hexahydro-1H-4,7-methano-1,2,3-benzotriazole
• CAS NO: 1975-39-9
• Molecular Formula: C₁₃H₁₅N₃
• Molecular Weight: 213.2783
• Mol File: 1975-39-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 318.5°C at 760 mmHg
• Flash Point: 146.4°C
• Density: 1.44g/cm³
• Vapor Pressure: 0.00036mmHg at 25°C
• Refractive Index: 1.783
• CAS DataBase Reference: 1-phenyl-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanobenzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanobenzotriazole(1975-39-9)
• EPA Substance Registry System: 1-phenyl-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanobenzotriazole(1975-39-9)

Safety Data

• Hazardous Substances Data: 1975-39-9(Hazardous Substances Data)

Usage

Chemical class

Benzotriazoles, a widely used corrosion inhibitor and UV stabilizer.

Structure

Hexahydro derivative of benzotriazole.

Appearance

White crystalline solid.

Molecular weight

204.28 g/mol.

Potential applications

Automotive and aerospace industries for metal corrosion protection and UV protection.

Ongoing research

Possible applications in materials science and surface coatings.

Upstream product

• 498-66-8 norborn-2-ene 
• 622-37-7 Phenyl azide 
• 498-66-8 norbornene 
• 2534-77-2 exo-2-bromonorbornane 
• 497-37-0 exo-2-norbornanol 
• 1516-59-2 3-nitrophenyl azide 

Relevant articles and documents

1,3-Dipolar cycloaddition of phenyl azide to norbornene in aqueous solutions

Second-order rate constants for the cycloaddition of phenyl azide to norbomene were determined in aqueous solutions. In organic solvents this reaction shows a very small solvent effect. In highly aqueous media, however, remarkable accelerations are observed. The solvent dependence of the rate constants on solvent composition in mixed aqueous solutions resembles those observed for Diels-Alder reactions, most likely because both types of cycloadditions are mechanistically related.

1,3-Dipolar cycloaddition reactivities of perfluorinated aryl azides with enamines and strained dipolarophiles

The reactivities of enamines and predistorted (strained) dipolarophiles toward perfluoroaryl azides (PFAAs) were explored experimentally and computationally. Kinetic analyses indicate that PFAAs undergo (3 + 2) cycloadditions with enamines up to 4 orders of magnitude faster than phenyl azide reacts with these dipolarophiles. DFT calculations were used to identify the origin of this rate acceleration. Orbital interactions between the cycloaddends are larger due to the relatively low-lying LUMO of PFAAs. The triazolines resulting from PFAA-enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditions of enamines and phenyl azide yield stable, isolable triazolines. The 1,3-dipolar cycloadditions of norbornene and DIBAC also show increased reactivity toward PFAAs over phenyl azide but are slower than enamine-azide cycloadditions.

REACTIVITY OF SUBSTITUTED NORBORNENES IN 1,3-DIPOLAR CYCLOADDITION WITH ARYL AZIDES

The reactivity of aryl azides in 1,3-dipolar cycloaddition with substituted norbornenes was determinated.In the series of investigated compounds the activity of the addends is determined primarily by the orbital donor-acceptor interactions.Description of the reactivity of the dipolarophiles with wide variation in the structure of the cyclenes requires consideration of the localization energies in addition to the donor-acceptor characteristics.