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Chemistry
Heterocyclic Building Blocks
Imidazoles
1,3-Dimesityl-4,5-dimethyl-1H-imidazol-3-ium chloride
Chemistry
Heterocyclic Building Blocks
Imidazoles

[ CAS No. 1118916-80-5 ]

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Chemical Structure| 1118916-80-5
Chemical Structure| 1118916-80-5
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Quality Control of [ 1118916-80-5 ]

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Product Details of [ 1118916-80-5 ]

CAS No. :1118916-80-5 MDL No. :N/A
Formula : C23H29ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :368.94 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1118916-80-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1118916-80-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1118916-80-5 ]

[ 1118916-80-5 ] Synthesis Path-Downstream   1~24

  • 1
  • C23H31N2O(1+)*Cl(1-) [ No CAS ]
  • [ 1118916-80-5 ]
YieldReaction ConditionsOperation in experiment
985 mg With hydrogenchloride; acetic anhydride In water; toluene at 90℃; for 13.5h;
Reference： [1]Hirano, Keiichi; Urban, Slawomir; Wang, Congyang; Glorius, Frank [Organic Letters, 2009, vol. 11, # 4, p. 1019 - 1022]
  • 2
  • [ 12112-67-3 ]
  • [ 1118916-80-5 ]
  • ((CH3)2C3N2(C6H2(CH3)3)2)Ir(C8H12)Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With KO-t-Bu In tetrahydrofuran imidazolium salt, KO-t-Bu and Ir complex reacted in THF at room temp. for 16 h;
Reference： [1]Urban, Slawomir; Tursky, Matyas; Froehlich, Roland; Glorius, Frank [Dalton Transactions, 2009, # 35, p. 6934 - 6940]
  • 3
  • [ 124-38-9 ]
  • [ 1118916-80-5 ]
  • [ 1188360-03-3 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride With potassium hexamethylsilazane In toluene for 2h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; toluene at 20℃;
Reference： [1]Location in patent: experimental part Van Ausdall, Bret R.; Glass, Jeremy L.; Wiggins, Kelly M.; Aarif, Atta M.; Louie, Janis [Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7935 - 7942]
  • 4
  • [ 1118916-80-5 ]
  • [ 2923-28-6 ]
  • [ 1188905-46-5 ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 1h;
Reference： [1]Location in patent: scheme or table Urban, Slawomir; Tursky, Matyas; Froehlich, Roland; Glorius, Frank [Dalton Transactions, 2009, # 35, p. 6934 - 6940]
  • 5
  • [ 1118916-80-5 ]
  • [ 848085-28-9 ]
YieldReaction ConditionsOperation in experiment
72% With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 1h; Glovebox; Inert atmosphere;
Reference： [1]Kinuta, Hirotaka; Tobisu, Mamoru; Chatani, Naoto [Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1593 - 1600]
  • 6
  • [ 88-05-1 ]
  • [ 1118916-80-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / neat (no solvent) / 3 h / 160 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 24 h / 110 °C 2.2: 15 h / 90 °C
Multi-step reaction with 2 steps 1: formic acid / methanol; water / 48 h / 0 - 20 °C 2: hydrogenchloride / 1,4-dioxane; ethyl acetate / 8 h / 20 °C
Multi-step reaction with 2 steps 1: formic acid / methanol / 24 h / 20 °C 2: hydrogenchloride / 1,4-dioxane / 3 h / Milling; Green chemistry
Multi-step reaction with 2 steps 1.1: acetic acid / 3.5 h / 140 - 160 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 110 °C 2.2: 13.5 h / 90 °C

Reference： [1]Kinuta, Hirotaka; Tobisu, Mamoru; Chatani, Naoto [Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1593 - 1600]
[2]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866]
[3]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Green Chemistry, 2018, vol. 20, # 5, p. 964 - 968]
[4]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN112110801, 2020, A
  • 7
  • [ 75105-48-5 ]
  • [ 4091-39-8 ]
  • [ 1118916-80-5 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: N,N'-dimesitylformamidine; 3-chloro-2-butanone With N-ethyl-N,N-diisopropylamine In acetonitrile at 110℃; for 20h; Stage #2: With hydrogenchloride; acetic anhydride In water; toluene at 90℃; for 13.5h; The product A (3.0mmol, 841mg, 1 equiv) obtained in the previous step,Acetonitrile (6.0mL) was placed in a 25mL round bottom flask,Then add diisopropylethylamine (3.6mmol, 0.59mL, 1.2equiv)And 3-chloro-2-butanone (6.0mmol, 0.61mL, 2equiv)Add dropwise to a round bottom flask, and stir the reaction solution at 110° C. for 20 h.The progress of the reaction was monitored by TLC (CH2Cl2/MeOH = 10:1).After the raw materials are reacted, the low boiling solvent is removed by rotary evaporation.Dissolve the residue in toluene (7.6mL),In acetic anhydride (9.0 mmol, 0.85 mL, 3 equiv) and 0.38 mL of 37% hydrochloric acid (4.5 mmol HCl, 1.5 equiv), the mixture was stirred at 90° C. for 13.5 h. After the completion of the reaction, the reaction was monitored by TLC (CH2Cl2/MeOH=10:1). The mixture was transferred to a separatory funnel containing CH2Cl2/H2O=1:1 (100 mL). After the two phases were separated, the aqueous layer was extracted with CH2Cl2 (3 times×50mL/time), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the crude product was spin-dried. After that, it was separated by column chromatography. The target product (CH2Cl2 :MeOH=10:1, Rf=0.6), the solvent was removed by a rotary evaporator to obtain the target product B as a white solid (985 mg, 89%).
68% Stage #1: N,N'-dimesitylformamidine; 3-chloro-2-butanone With N-ethyl-N,N-diisopropylamine In acetonitrile at 110℃; for 24h; Stage #2: With hydrogenchloride; acetic anhydride In water; toluene; acetonitrile at 90℃; for 15h;
Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN112110801, 2020, A Location in patent: Paragraph 0029-0030
[2]Kinuta, Hirotaka; Tobisu, Mamoru; Chatani, Naoto [Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1593 - 1600]
  • 8
  • [ 1118916-80-5 ]
  • [ 436-59-9 ]
  • C41H49BN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane at -78℃; for 3h;
Reference： [1]McDonald, Sean M.; Mellerup, Soren K.; Peng, Jinbao; Yang, Dengtao; Li, Quan-Song; Wang, Suning [Chemistry - A European Journal, 2015, vol. 21, # 40, p. 13961 - 13970]
  • 9
  • [ 1118916-80-5 ]
  • [ 436-59-9 ]
  • C32H37BN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 °C 2.1: benzene-d6 / 72 h / UV-irradiation
Reference： [1]McDonald, Sean M.; Mellerup, Soren K.; Peng, Jinbao; Yang, Dengtao; Li, Quan-Song; Wang, Suning [Chemistry - A European Journal, 2015, vol. 21, # 40, p. 13961 - 13970]
  • 10
  • [ 1271-28-9 ]
  • [ 1118916-80-5 ]
  • [Ni(η5-C5H5)(Cl)(IMes2Me)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In tetrahydrofuran for 3h; Inert atmosphere; Schlenk technique; Reflux;
Reference： [1]Banach, Łukasz; Guńka, Piotr A.; Gõrska, Dominika; Podlewska, Maja; Zachara, Janusz; Buchowicz, Włodzimierz [European Journal of Inorganic Chemistry, 2015, vol. 2015, # 34, p. 5677 - 5686]
  • 11
  • [ 1118916-80-5 ]
  • [ 20667-12-3 ]
  • [AgCl(IMesMe)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Darkness;
Reference： [1]Michalska, Malina; Grela, Karol [Synlett, 2016, vol. 27, # 4, p. 599 - 603]
  • 12
  • [ 1118916-80-5 ]
  • C23H28AuClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / Darkness 2: dichloromethane
Reference： [1]Michalska, Malina; Grela, Karol [Synlett, 2016, vol. 27, # 4, p. 599 - 603]
  • 13
  • [ 50-00-0 ]
  • [ 202277-65-4 ]
  • [ 1118916-80-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane; ethyl acetate at 20℃; for 8h;
156 mg With hydrogenchloride In 1,4-dioxane for 3h; Milling; Green chemistry;
Reference： [1]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866]
[2]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Green Chemistry, 2018, vol. 20, # 5, p. 964 - 968]
  • 14
  • [ 1118916-80-5 ]
  • [1,3-bis(2,4,6-trimethylphenyl)-4,5-dimethyl]imidazolium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
429.2 mg With potassium hexafluorophosphate In water for 0.5h;
Reference： [1]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866]
  • 15
  • [ 1118916-80-5 ]
  • bis[(1,3-bis(2,4,6-trimethylphenyl)-4,5-dimethyl)imidazol-2-ylidene]silver tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water / 0.5 h 2: sodium hydroxide / 3 h / Milling
Reference： [1]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866]
  • 16
  • [ 1118916-80-5 ]
  • bis[(1,3-bis(2,4,6-trimethylphenyl)-4,5-dimethyl)imidazol-2-ylidene]silver hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hexafluorophosphate / water / 0.5 h 2: sodium hydroxide / 3 h / Milling
Reference： [1]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866]
  • 17
  • [ 13755-29-8 ]
  • [ 1118916-80-5 ]
  • 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
434.9 mg In water for 0.5h;
Reference： [1]Beillard, Audrey; Bantreil, Xavier; Métro, Thomas-Xavier; Martinez, Jean; Lamaty, Frédéric [Dalton Transactions, 2016, vol. 45, # 44, p. 17859 - 17866]
  • 18
  • chloro(1,5-cyclooctadiene)rhodium(I) dimer [ No CAS ]
  • [ 1118916-80-5 ]
  • C31H40ClN2Rh [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In (2)H8-toluene at 60℃; for 1h; Glovebox;
Reference： [1]Tobisu, Mamoru; Yasui, Kosuke; Aihara, Yoshinori; Chatani, Naoto [Angewandte Chemie - International Edition, 2017, vol. 56, # 7, p. 1877 - 1880][Angew. Chem., 2017, vol. 129, p. 1903 - 1906]
  • 19
  • chloro(1,5-cyclooctadiene)rhodium(I) dimer [ No CAS ]
  • [ 1118916-80-5 ]
  • C92H112Cl2N8Rh2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In (2)H8-toluene at 20℃; for 1h; Glovebox;
Reference： [1]Tobisu, Mamoru; Yasui, Kosuke; Aihara, Yoshinori; Chatani, Naoto [Angewandte Chemie - International Edition, 2017, vol. 56, # 7, p. 1877 - 1880][Angew. Chem., 2017, vol. 129, p. 1903 - 1906]
  • 20
  • chlorobis(ethylene)rhodium(I) dimer [ No CAS ]
  • [ 1118916-80-5 ]
  • C69H84ClN6Rh [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In (2)H8-toluene at 60℃; for 1h; Glovebox;
Reference： [1]Tobisu, Mamoru; Yasui, Kosuke; Aihara, Yoshinori; Chatani, Naoto [Angewandte Chemie - International Edition, 2017, vol. 56, # 7, p. 1877 - 1880][Angew. Chem., 2017, vol. 129, p. 1903 - 1906]
  • 21
  • [ 1118916-80-5 ]
  • copper [ No CAS ]
  • [ 1446705-82-3 ]
YieldReaction ConditionsOperation in experiment
82% With air In benzonitrile for 6h; Milling;
Reference： [1]Beillard, Audrey; Métro, Thomas-Xavier; Bantreil, Xavier; Martinez, Jean; Lamaty, Frédéric [Chemical Science, 2017, vol. 8, # 2, p. 1086 - 1089]
  • 22
  • [ 100-42-5 ]
  • [ 1295-35-8 ]
  • [ 1118916-80-5 ]
  • [(IMesMe)Ni(styrene)2] [ No CAS ]
Reference： [1]Organometallics,2018,vol. 37,p. 3687 - 3697
  • 23
  • [ 91-22-5 ]
  • [ 1118916-80-5 ]
  • [ 1056451-44-5 ]
YieldReaction ConditionsOperation in experiment
76% With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium t-butanolate at 200℃; for 18h; Glovebox; Inert atmosphere; Sealed tube;
Reference： [1]Sakurai, Shun; Tobisu, Mamoru [Organometallics, 2019, vol. 38, # 14, p. 2834 - 2838]
  • 24
  • [ 1118916-80-5 ]
  • N-(4-bromonaphthalen-1-yl)-N-methylmethacrylamide [ No CAS ]
  • C38H43N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate In toluene at 150℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
Reference： [1]Hu, Yuanyuan; Wang, Zhen; Luo, Honggen; Jin, Hongwei; Liu, Yunkui; Zhou, Bingwei [Organic and Biomolecular Chemistry, 2021, vol. 19, # 17, p. 3834 - 3837]

Tags: 1118916-80-5 synthesis path| 1118916-80-5 SDS| 1118916-80-5 COA| 1118916-80-5 purity| 1118916-80-5 application| 1118916-80-5 NMR| 1118916-80-5 COA| 1118916-80-5 structure

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