Production Method 1

14874-70-5

286014-24-2

578743-87-0

14874-70-5

886061-46-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Acetonitrile ;  2 h, 80 °C

Reference

Synthesis of Homoleptic and Heteroleptic Bis-N-heterocylic Carbene Group 11 Complexes

Lazreg, Faima; Cordes, David B.; Slawin, Alexandra M. Z.; Cazin, Catherine S. J., Organometallics, 2015, 34(2), 419-425

Production Method 2

250285-32-6

14874-70-5

886061-46-7

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide ,  Tetrakis(acetonitrile)copper(1+) tetrafluoroborate Solvents: Tetrahydrofuran ;  6 h, rt

Reference

Cationic Copper(I) Complexes as Efficient Precatalysts for the Hydrosilylation of Carbonyl Compounds

Diez-Gonzalez, Silvia; Scott, Natalie M.; Nolan, Steven P., Organometallics, 2006, 25(9), 2355-2358

Production Method 3

14874-70-5

43625-65-6

14874-70-5

830317-15-2

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 4

14874-70-5

830317-15-2

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 5

14874-70-5

830317-15-2

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 6

14874-70-5

830317-15-2

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 7

14874-70-5

43625-65-6

14874-70-5

830317-15-2

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 8

14874-70-5

830317-15-2

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 9

14874-70-5

43625-65-6

14874-70-5

830317-15-2

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 10

25583-69-1

14874-70-5

830317-15-2

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 11

14874-70-5

43625-65-6

31410-01-2

14874-70-5

98806-09-8

Reaction Conditions

1.1 Solvents: Hexane ;  10 min, -78 °C; -78 °C → rt

Reference

Allyl-functionalised ionic liquids: synthesis, characterisation, and reactivity

Zhao, Dongbin; Fei, Zhaofu; Geldbach, Tilmann J.; Scopelliti, Rosario; Laurenczy, Gabor; et al, Helvetica Chimica Acta, 2005, 88(3), 665-675

Production Method 12

65039-10-3

14874-70-5

98806-09-8

Reaction Conditions

1.1 Reagents: Sodium tetrafluoroborate Solvents: Dichloromethane ;  12 h, 25 °C

Reference

Direct Synthesis of Imidazolium-Functional Polyethylene by Insertion Copolymerization

Jian, Zhongbao; Leicht, Hannes; Mecking, Stefan, Macromolecular Rapid Communications, 2016, 37(11), 934-938

Production Method 13

65039-10-3

14874-70-5

98806-09-8

Reaction Conditions

1.1 Reagents: Tetrafluoroboric acid ;  2 h, rt

Reference

Polymeric ionic liquid modified silica for CO2 adsorption and diffusivity

Sun, Yachai; Zhu, Jiamei; Huang, Junhua; Xin, Feng; Liu, Jingxia, Polymer Composites, 2017, 38(4), 759-766

Production Method 14

14874-70-5

1242995-21-6

286014-24-2

14874-70-5

886061-46-7

Reaction Conditions

1.1 Solvents: Acetonitrile ;  1 h, 80 °C

Reference

Heteroleptic Bis(N-heterocyclic carbene)Copper(I) Complexes: Highly Efficient Systems for the [3+2] Cycloaddition of Azides and Alkynes

Lazreg, Faima; Slawin, Alexandra M. Z.; Cazin, Catherine S. J., Organometallics, 2012, 31(22), 7969-7975

Production Method 15

14874-70-5

286014-24-2

14874-70-5

886061-46-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Copper ,  Oxygen ;  5 h, rt

Reference

Cu(0), O2 and mechanical forces: a saving combination for efficient production of Cu-NHC complexes

Beillard, Audrey; Metro, Thomas-Xavier; Bantreil, Xavier; Martinez, Jean; Lamaty, Frederic, Chemical Science, 2017, 8(2), 1086-1089

Production Method 16

1072-63-5

14874-70-5

45534-45-0

Reaction Conditions

1.1 Reagents: Ammonium tetrafluoroborate Solvents: Dimethylformamide ;  10 min, 150 °C

Reference

Rapid Continuous-Flow Water-Free Synthesis of Ultrapure Ionic Liquids Assisted by Microwaves

Cao, Lei; et al, Organic Process Research & Development (2022, Organic Process Research & Development (2022), 26(1), 207-214, 26(1), 207-214

Production Method 17

1072-63-5

14874-70-5

45534-45-0

Reaction Conditions

1.1 Catalysts: Azobisisobutyronitrile Solvents: Dimethylformamide ;  24 h, 70 °C
2.1 Reagents: Ammonium tetrafluoroborate Solvents: Dimethylformamide ;  10 min, 150 °C

Reference

Rapid Continuous-Flow Water-Free Synthesis of Ultrapure Ionic Liquids Assisted by Microwaves

Cao, Lei; et al, Organic Process Research & Development (2022, Organic Process Research & Development (2022), 26(1), 207-214, 26(1), 207-214

Production Method 18

14874-70-5

830317-15-2

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 19

14874-70-5

43625-65-6

14874-70-5

830317-15-2

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 20

14874-70-5

43625-65-6

14874-70-5

830317-15-2

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 21

14874-70-5

830317-15-2

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 22

14874-70-5

830317-15-2

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

Production Method 23

616-47-7

14874-70-5

98806-09-8

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  Diisopropyl azodicarboxylate Solvents: Acetonitrile ;  15 h, rt

Reference

An efficient protocol for the preparation of pyridinium and imidazolium salts based on the Mitsunobu reaction

Petit, Sylvain; Azzouz, Rabah; Fruit, Corinne; Bischoff, Laurent; Marsais, Francis, Tetrahedron Letters, 2008, 49(22), 3663-3665

Production Method 24

616-47-7

14874-70-5

98806-09-8

Reaction Conditions

1.1 Solvents: Acetonitrile ;  0 °C; 24 - 48 h, 30 °C
1.2 Reagents: Sodium tetrafluoroborate Solvents: Acetone ;  24 h, rt

Reference

Synthesis and properties of ionic liquids: imidazolium tetrafluoroborates with unsaturated side chains

Min, Gwan-Hong; Yim, Taeeun; Lee, Hyun Yeong; Huh, Dal Ho; Lee, Eunjoo; et al, Bulletin of the Korean Chemical Society, 2006, 27(6), 847-852

Production Method 25

31410-01-2

14874-70-5

98806-09-8

Reaction Conditions

1.1 Reagents: Tetrafluoroboric acid Solvents: Water ;  0 °C; 1 h, 0 °C → rt
1.2 10 min, 150 °C

Reference

Rapid Continuous-Flow Water-Free Synthesis of Ultrapure Ionic Liquids Assisted by Microwaves

Cao, Lei; Kim, Hong Won; Jeong, Yu Jin; Han, Seung Chang; Park, Jin Kyoon, Organic Process Research & Development, 2022, 26(1), 207-214

Production Method 26

31410-01-2

14874-70-5

98806-09-8

Reaction Conditions

1.1 Reagents: Ammonium tetrafluoroborate ;  22 h, 110 °C

Reference

A general and direct synthesis of imidazolium ionic liquids using orthoesters

Kim, Do Joong; Oh, Kyung Hwan; Park, Jin Kyoon, Green Chemistry, 2014, 16(9), 4098-4101

Production Method 27

65039-10-3

14874-70-5

98806-09-8

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Acetone ;  24 h, rt

Reference

Preparation of ionic liquids containing unsaturated double bonds for use in cellulose dissolving and derivatizing

, China, , ,

Production Method 28

14874-70-5

150-78-7

140681-54-5

14874-70-5

82830-49-7

Reaction Conditions

1.1 Solvents: Acetonitrile ;  3 - 6 h, rt; 2 - 5 h, rt

Reference

Arene Amination Instead of Fluorination: Substitution Pattern Governs the Reactivity of Dialkoxybenzenes with Selectfluor

Capilato, Joseph N. ; et al, Journal of Organic Chemistry, 2021, 86(8), 5771-5777

Borate(1-),tetrafluoro- Raw materials

• Borate(1-),tetrafluoro-
• 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride
• 1-Allyl-3-methylimidazolium chloride
• 1,4-Dimethoxybenzene
• Oxonium, trimethyl-(9CI)
• 2-PYRROLIDINONE, PHENYLHYDRAZONE
• Copper, [1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]hydroxy-
• 1-Vinylimidazole
• 1-Allylimidazole
• 1-Methylimidazole
• 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-
• 1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane
• [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-chloro-copper

Borate(1-),tetrafluoro- Preparation Products

• 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-4-ium (830317-15-2)
• 2-Fluoro-1,4-dimethoxybenzene (82830-49-7)
• Borate(1-),tetrafluoro- (14874-70-5)
• Copper(1+), bis[1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]- (886061-46-7)
• 1-Ethenyl-3-methylimidazol-3-ium (45534-45-0)
• 1H-Imidazolium, 1-methyl-3-(2-propenyl)- (98806-09-8)

• 1. A diastereoselective cobalt-mediated synthesis of benzopyrans using a novel variation of an intramolecular Nicholas reaction in the key cyclisation step: optimisation and biological evaluation?1
  Alastair Mann,Christophe Muller,Elizabeth Tyrrell J. Chem. Soc. Perkin Trans. 1 1998 1427
• 2. Study of the spontaneous attachment of polycyclic aryldiazonium salts onto amorphous carbon substrates
  Deirdre M. Murphy,Ronan J. Cullen,Dilushan R. Jayasundara,Eoin M. Scanlan,Paula E. Colavita RSC Adv. 2012 2 6527
• 3. Theoretical insights into structure, bonding, reactivity and importance of ion-pair interactions in Kirby's tetrafluoroboric acid salts of twisted amides
  Krishna K. Pandey RSC Adv. 2015 5 105668
• 4. Structures and phase transitions in molecular complexes containing tetrafluoroboric acid and tetramethylpyrazine
  M. Rok,P. Szklarz,G. Bator CrystEngComm 2018 20 5772
• 5. Structures and phase transitions in molecular complexes containing tetrafluoroboric acid and tetramethylpyrazine
  M. Rok,P. Szklarz,G. Bator CrystEngComm 2018 20 5772

• 459-45-0(4-fluorobenzene-1-diazonium; tetrafluoroboranuide)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)