7167-29-5

Basic information

• Product Name: 3-(3-bromo-1H-1,2,4-triazol-1-yl)-N-[4-(difluoromethoxy)-3-methoxyphenyl]tricyclo[3.3.1.1~3,7~]decane-1-carboxamide
• Synonyms: 3-(3-Bromo-1H-1,2,4-triazol-1-yl)-N-[4-(difluoromethoxy)-3-methoxyphenyl]adamantane-1-carboxamide; tricyclo[3.3.1.1~3,7~]decane-1-carboxamide, 3-(3-bromo-1H-1,2,4-triazol-1-yl)-N-[4-(difluoromethoxy)-3-methoxyphenyl]-
• CAS NO: 7167-29-5
• Molecular Formula: C₂₁H₂₃BrF₂N₄O₃
• Molecular Weight: 497.3331
• Mol File: 7167-29-5.mol
• Article Data: 16

Chemical Properties

• Density: 1.7g/cm³
• Refractive Index: 1.691
• CAS DataBase Reference: 3-(3-bromo-1H-1,2,4-triazol-1-yl)-N-[4-(difluoromethoxy)-3-methoxyphenyl]tricyclo[3.3.1.1~3,7~]decane-1-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-bromo-1H-1,2,4-triazol-1-yl)-N-[4-(difluoromethoxy)-3-methoxyphenyl]tricyclo[3.3.1.1~3,7~]decane-1-carboxamide(7167-29-5)
• EPA Substance Registry System: 3-(3-bromo-1H-1,2,4-triazol-1-yl)-N-[4-(difluoromethoxy)-3-methoxyphenyl]tricyclo[3.3.1.1~3,7~]decane-1-carboxamide(7167-29-5)

Safety Data

• Hazardous Substances Data: 7167-29-5(Hazardous Substances Data)

Upstream product

• 6203-08-3 methyl 5-norbornene-2-carboxylate 
• 74-88-4 methyl iodide 
• 77-73-6 bi(cyclopentadiene) 
• 542-92-7 cyclopenta-1,3-diene 
• 80-62-6 methacrylic acid methyl ester 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 
• 13432-80-9 (+/-)-6c-iodo-3-methyl-(3ar)-hexahydro-3,5-methano-cyclopenta[b]furan-2-one 
• 769-85-7 methyl exo-5-norbornene-2-carboxylate 

Downstream Products

• 87729-25-7 6-exo-(Benzoyloxy)-2-endo-<(benzoyloxy)methyl>-2-exo-methylbicyclo<2.2.1>heptane 

Relevant articles and documents

Hydrogen-bond-rich ionic liquids as effective organocatalysts for Diels-Alder reactions

The synthesis and characterisation of new hydrogen-bond-rich ionic liquids and studies of their catalytic performance in Diels-Alder reactions are described. d-Glucose and chloroalcohols were used as the raw materials and as the sources of hydroxyl groups for the synthesis of ionic-liquid cations, whereas weakly coordinating bis(trifluoromethylsulfonyl)imide was used as the anion. The new ionic liquids were analysed by 1H and 13C NMR spectroscopy and by ESI-MS experiments, which confirmed their structures. In addition, the thermal data of the studied ionic liquids measured by differential scanning calorimetry and thermogravimetric analysis showed that these compounds tend to form a glass at temperatures in the range of -29°C to -16°C and are thermally stable from ambient temperature to at least 430°C, most likely because of the presence of bis(trifluoromethylsulfonyl) imide anions. The performance of the ionic liquids in the model reaction of cyclopentadiene with diethyl maleate or methyl acrylate was investigated. The studied ionic liquids showed high activity even when present in catalytic amounts (4 mol% with respect to the dienophile). An increase in the number of hydroxyl groups present in the ionic liquid structure resulted in higher reaction rates. This journal is the Partner Organisations 2014.

Converting exo-Selective Diels-Alder Reaction to endo-Selective in Chloroloaluminate Ionic Liquids

The endo:exo ratio of 0.35:1 for the reaction of cyclopentadiene with methyl methacrylate observed in organic solvents can be converted to 3:1 in chloroaluminate ionic liquids with their effective reuse in Diels-Alder reactions.

Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels-Alder reaction

N-trimethylsilyl bis(trifluoromethanesulfonyl)imide (TMSNTf2) was readily prepared in situ by protodesilylation of trimethylsilane, allyl- or phenyltrimethylsilane with bis(trifluoromethylsulfonyl)imide. NMR studies showed that TMSNTf2 was much more effective than TMSOTf in complexing the carbonyl group of trans-methylcrotonate. As a result, TMSNTf2 was found to be superior to TMSOTf as a catalyst for the Diels-Alder reaction of α,β-unsaturated esters with a wide variety of dienes. In contrast to many metal derived Lewis acids, TMSNTf2 was found tolerant of many sensitive functional groups present in the diene partner.