Production Method 1

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  24 h, rt
1.2 24 h, rt
1.3 Solvents: Chlorobenzene ;  24 h, 120 °C

Reference

Rerouting the Organocatalytic Benzoin Reaction toward Aldehyde Deuteration

Gadekar, Santosh C.; Dhayalan, Vasudevan; Nandi, Ashim; Zak, Inbal L.; Mizrachi, Meital Shema; et al, ACS Catalysis, 2021, 11(23), 14561-14569

Production Method 2

14874-70-5

43625-65-6

830317-15-2

14874-70-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  overnight, rt
1.2 overnight, rt
1.3 Reagents: Triethyl orthoformate Solvents: Methanol ;  overnight, reflux

Reference

From Furfural to Fuel: Synthesis of Furoins by Organocatalysis and their Hydrodeoxygenation by Cascade Catalysis

Wegenhart, Benjamin L.; Yang, Linan; Kwan, Soon Cheong; Harris, Remi; Kenttaemaa, Hilkka I.; et al, ChemSusChem, 2014, 7(9), 2742-2747

Production Method 3

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  overnight, rt
1.2 2 d, rt
1.3 Solvents: Methanol ;  overnight, 100 °C

Reference

Probing the Efficiency of N-Heterocyclic Carbene Promoted O- to C-Carboxyl Transfer of Oxazolyl Carbonates

Thomson, Jennifer E.; Campbell, Craig D.; Concellon, Carmen; Duguet, Nicolas; Rix, Kathryn; et al, Journal of Organic Chemistry, 2008, 73(7), 2784-2791

Production Method 4

14874-70-5

43625-65-6

830317-15-2

14874-70-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  24 h, rt
1.2 48 h, rt
1.3 Reagents: Triethyl orthoformate Solvents: Methanol ;  overnight, rt → reflux

Reference

A model β-sheet interaction and thermodynamic analysis of β-strand mimetics

Robinson, Colin W.; Rye, Carl S.; Chessum, Nicola E. A.; Jones, Keith, Organic & Biomolecular Chemistry, 2015, 13(27), 7402-7407

Production Method 5

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  18 h, rt
1.2 18 h, rt
1.3 Solvents: Toluene ;  48 h, reflux

Reference

N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

Romanov-Michailidis, Fedor; Besnard, Celine; Alexakis, Alexandre, Organic Letters, 2012, 14(18), 4906-4909

Production Method 6

25583-69-1

830317-15-2

14874-70-5

Reaction Conditions

1.1 Solvents: Triethyl orthoformate ;  24 - 48 h, reflux

Reference

The Role of the Fused Ring in Bicyclic Triazolium Organocatalysts: Kinetic, X-ray, and DFT Insights

Zhu, Jiayun ; Moreno, Inmaculada; Quinn, Peter; Yufit, Dmitry S.; Song, Lijuan; et al, Journal of Organic Chemistry, 2022, 87(6), 4241-4253

Production Method 7

14874-70-5

43625-65-6

830317-15-2

14874-70-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  overnight, rt
1.2 2 d, rt
1.3 Solvents: Methanol ,  Triethyl orthoformate ;  overnight, 100 °C

Reference

Efficient N-Heterocyclic Carbene-Catalyzed O- to C-Acyl Transfer

Thomson, Jennifer E.; Rix, Kathryn; Smith, Andrew D., Organic Letters, 2006, 8(17), 3785-3788

Production Method 8

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  24 h, rt
1.2 24 h, rt
1.3 Solvents: Chlorobenzene ;  24 h, 120 °C

Reference

Rerouting an organocatalytic reaction by intercepting its reactive intermediates

Gadekar, Santosh C.; Dhayalan, Vasudevan; Nandi, Ashim; Zak, Inbal L.; Barkai, Shahar; et al, ChemRxiv, 2020, 1, 1-9

Production Method 9

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  overnight, rt
1.2 2 d, rt
1.3 Solvents: Methanol ;  overnight, 100 °C

Reference

Selective Synthesis of Acylated Cross-Benzoins from Acylals and Aldehydes via N-Heterocyclic Carbene Catalysis

Onodera, Kou; Takashima, Ryo; Suzuki, Yumiko, Organic Letters, 2021, 23(11), 4197-4202

Production Method 10

14874-70-5

43625-65-6

830317-15-2

14874-70-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  overnight, rt
1.2 Reagents: (Pentafluorophenyl)hydrazine ;  24 h, rt
1.3 Reagents: Triethyl orthoformate Solvents: Methanol ,  Chlorobenzene ;  overnight, 120 °C

Reference

N-heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: efficient synthesis of α-amino-β-keto esters

Uno, Takuya; Kobayashi, Yusuke; Takemoto, Yoshiji, Beilstein Journal of Organic Chemistry, 2012, 8, 1499-1504

Production Method 11

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  overnight, rt
1.2 5 d, rt
1.3 overnight, 100 °C

Reference

NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates

Wu, Terence; Tatton, Matthew R.; Greaney, Michael F., Angewandte Chemie, 2022, 61(15),

Production Method 12

14874-70-5

43625-65-6

830317-15-2

14874-70-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  overnight, rt
1.2 2 d, rt
1.3 Reagents: Tetrafluoroboric acid Solvents: Methanol ;  overnight, reflux

Reference

N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling

Nicholson, William I.; Seastram, Alex C.; Iqbal, Saqib A.; Reed-Berendt, Benjamin G.; Morrill, Louis C.; et al, ChemSusChem, 2020, 13(1), 131-135

Production Method 13

830317-15-2

14874-70-5

Reaction Conditions

1.1 Reagents: Trimethyloxonium tetrafluoroborate Solvents: Dichloromethane ;  18 h, rt
1.2 overnight, rt
1.3 Solvents: Toluene ;  48 h, reflux

Reference

The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide

Konstandaras, Nicholas; Dunn, Michelle H.; Guerry, Max S.; Barnett, Christopher D.; Cole, Marcus L.; et al, Organic & Biomolecular Chemistry, 2020, 18(1), 66-75

2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-4-ium Raw materials

• Borate(1-),tetrafluoro-
• Oxonium, trimethyl-(9CI)
• 2-PYRROLIDINONE, PHENYLHYDRAZONE

2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-4-ium Preparation Products

• 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-4-ium (830317-15-2)
• Borate(1-),tetrafluoro- (14874-70-5)

• 1. Fc microparticles can modulate the physical extent and magnitude of complement activity?
  David White,Sean R. Stowell Biomater. Sci., 2017,5, 463-474
• 2. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 3. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 4. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 5. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991

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