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Product Details of [ 21876-43-7 ]

CAS No. :21876-43-7 MDL No. :MFCD34167164
Formula : C9H13NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 215.27 Pubchem ID :-
Synonyms :

Safety of [ 21876-43-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21876-43-7 ]

* 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 [ 21876-43-7 ]

[ 21876-43-7 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 110-86-1 ]
  • [ 1633-83-6 ]
  • [ 21876-43-7 ]
YieldReaction ConditionsOperation in experiment
100% at 40℃; for 10h; Zwitterions synthesis:1 -H-Methylimidazole (8.21g, 0.1 mol) or 1,2 dimethylimidazole (9.61g, 0.1 mol) or pyridine (7.91g, 0,1 mol) and 1,4-butane sultone (13.62g, 0.1 mol) were charged into a 50 mL round bottom flask and stirred at 40°C for 10 hours. The white solid zwitterion was washed repeatedly with toluene (3x10 mL), cyclohexane (3x10 mL) and ether (5x10 mL) and dried under vacuum. The zwitterions were formed quantitatively.
97.6% at 70℃; 1 Example 11-(4-sulfonylbutyl)pyridinium; A mixture of pyridine (0.077 mol) and 1,4-butanesultone (0.07 mol) were heated with stirring at 70° C. overnight. On completion, the obtained white solid was washed three times with 80 mL of diethylether. Finally, the product was dried under vacuum. Yield 97.6%.
97.6% at 70℃; 1 1-(4-sulfonatobutyl)pyridinium A mixture of pyridine (0.077 mol) and 1 ,4-butanesultone (0.07 mol) were heated with stirring at 70°C overnight. On completion, the obtained white solid was washed three times with 80 mL of diethylether. Finally, the product was dried under vaccum. Yield 97.6%.
83% In ethanol at 20℃; for 120h; 2.1 Preparation of 1-(4-sulfobutyl)pyridinium betaine (1) 1,4-Butanesultone (2.72g, 20mmol) was added slowly to pyridine (20mmol) dissolved in 4ml EtOH. The mixture was stirred at room temperature for 120h. After the removal of ethanol in vacuum, the product was washed with toluene (3×25ml) and diethylether (2×25ml) to remove any unreacted starting material. The crude product was recrystallized from hot methanol to give 3.57g (83%) of 1. (0015) 1H NMR δ (DMSO-d6) 9.08-9.12 (m, 2H, 2,6-H); 8.60 (tt, J=1.4Hz, 7.7Hz, 1H, 4-H); 8.14-8.19 (m, 2H, 3,5-H); 4.63 (t, J=7.4Hz, 2H, NCH2); 2.43-2.49 (m, 2H, SCH2); 1.98-2.05 (m, 2H, NHCH2CH2); 1.53-1.61 (m, 2H, SCH2CH2). 13C NMR δ (DMSO-d6) 146.0; 145.3; 128.6; 61.1; 50.9; 30.5; 22.2. IR (KBr): 1630, 1487, 1172, 1037 cm-1
57% In acetonitrile at 80℃; for 24h;
at 40℃; for 24h;
0.006 mol In toluene at 40℃; for 24h; Inert atmosphere;
at 40℃; for 10h;
at 40 - 80℃; for 10h; 2.1. Synthesis and characterization of SO3H-ILs General procedure: 1-methylimidazol (99%, Sigma-Aldrich) or pyridine (>99%, Sigma-Aldrich) or triethylamine (>99.5%, Fluka) (0.2 mol) and 1,4-butanesultone (99%, Aldrich, 0.2 mol) were charged in a 100 ml round bottomed flask. The mixture was then stirred at 40-80 °C for 10 h. The solid zwitterion formed was recovered by filtration, washed repetitively with diethyl ether until all unreacted reactants were completely removed (confirmed by NMR) and then dried under reduced pressure (15 mbar, 50 °C) overnight.
In toluene Heating;
In toluene at 50℃; Inert atmosphere; 2.2. Preparation of PW-based ionic liquid salts General procedure: PW-based ILs were synthesized following the procedure in Scheme 1. As an example for the preparation of compound II, 4-phenyl-pyridine (PhPy) (1.55 g, 0.01 mol) and 1,4-butane sultone (Bs)(1.36 g, 0.01 mol) were dissolved in toluene (10 mL) and stirred at 50 °C for 48 h under nitrogen atmosphere. A white solid zwitterion PhPyBs was formed; it was filtered and washed with ether three times, then dried in a vacuum. The resulting PhPyBs (8.74 g, 0.03 mol)was added to the aqueous solution of H3PW12O40 (PW) (28.8 g,0.01 mol), followed by the stirring of the mixture at room temperature for 24 h. Water was removed in vacuum to give the final product as solid. QBs-PW (I) and PyBs-PW(III) were prepared based on the samemethod using the corresponding starting materials.
at 50℃; for 48h; Inert atmosphere; 2.2. Preparation of SO3H-functionalized POM-ILs General procedure: Isoquinoline (Q) (0.01 mol) and 1,4-butane sultone (Bs)(0.01 mol) were mixed and stirred at 50 C for 48 h under nitrogenatmosphere. A white solid zwitterion QBs was formed. Solid wasfiltered and washed with ether three times and dried in a vacuum.The resulting QBs (0.03 mol) was added to the aqueous solution of PMo (0.01 mol), stirred at room temperature for 24 h. Solvent wasevaporated vacuum to give the final solid product (QBs-PMo).PhPyBs-PW, PyBs-PW, QBs-PW and QBs-SiW were prepared basedon the same method using corresponding starting materials (Scheme 1) according to our previously published paper [26].
In toluene at 50℃; for 51h; Inert atmosphere; 2.2. Preparation of PW-based sulfonated Bronsted acidic IL catalysts General procedure: Isoquinoline (Q) (0.01 mol) and 1,4-butane sultone (Bs)(0.01 mol) were mixed at 50 C. After 3 h, 5 mL toluene was addedand stirred for 48 h under nitrogen atmosphere. A white solidzwitterion, QBs, was formed; it was filtered off and washed withether for three times, then dried in a vacuum. The resulting aqueoussolution of QBs (0.03 mol)was added to the aqueous solution of PW(0.01 mol), followed by the stirring of the mixture at room temperaturefor 24 h. Water was removed in vacuum to give the finalproduct as solid (QBs-PW). PhPyBs-PW and PyBs-PW were preparedbased on the same method with using corresponding startingmaterials (Scheme 1) according to our previously publishedpaper [31,32].
at 35℃; for 10h; 2 1,4-butane sultone (14. 98 g, 0.1 mol) was slowly added to a solution of pyridine (7 · 91 g, 0.1 mol)The mixture was stirred for 10 h and incubated at 35 ° C until the reactants were converted to a solid, washed thoroughly with ether and dried in an infrared oven.Take the above solid 7. 16g in a three-necked flask,periodic acid (9.12g, 0.04mol) aqueous solution was slowly added and stirred at 80 ° C for 36h. The [HS03-BPy] 104 acid ionic liquid oxidant was prepared by vacuum steaming.
at 40℃; for 24h;
In acetonitrile for 48h; Reflux;
In acetonitrile at 80℃; for 24h; [HSO3-BPy]H2PO4: To prepare the IL [HSO3-BPy]H2PO4, HSO3-BPy was prepared first. Toprepare HSO3-BPy, 0.1 mol (13.6 g) 1,4-butane sultone was mixed with 0.1 mol (7.9 g)pyridine in a flask containing 50 mL of acetonitrile. After 24 h of reflux at 80 C, the reactionmixture was cooled to room temperature and a precipitate was observed. The precipitate wascollected by filtration and washed twice with diethyl ether. The resulting white precipitatewas then dried in vacuum at 60 C for 4 h and HSO3-BPy was obtained.

Reference: [1]Current Patent Assignee: KONINKLIJKE DSM N.V. - WO2008/145312, 2008, A1 Location in patent: Page/Page column 9
[2]Current Patent Assignee: TECHNICAL UNIVERSITY OF DENMARK - US2011/65950, 2011, A1 Location in patent: Page/Page column 8
[3]Current Patent Assignee: TECHNICAL UNIVERSITY OF DENMARK - CN102625731, 2016, B Location in patent: Paragraph 0168-0170
[4]Fütyű, Júlia; Fehér, Csaba; Hancsók, Jenő; Ispán, Dávid; Juzsakova, Tatjána; Skoda-Földes, Rita; Szegedi, Ágnes [Molecular catalysis, 2022, vol. 518]
[5]Senapak; Saeeng; Jaratjaroonphong; Kasemsuk; Sirion [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1302 - 1310]
[6]Willems [Bulletin des Societes Chimiques Belges, 1955, vol. 64, p. 747,752, 768] Helberger; Lantermann [Justus Liebigs Annalen der Chemie, 1954, vol. 586, p. 158,163] Truce; Hoerger [Journal of the American Chemical Society, 1954, vol. 76, p. 5357,5360]
[7]Location in patent: experimental part Li, Kai-Xin; Chen, Li; Yan, Zong-Cheng; Wang, Hong-Lin [Catalysis Letters, 2010, vol. 139, # 3-4, p. 151 - 156]
[8]Location in patent: experimental part Li, Kaixin; Chen, Li; Wang, Honglin; Lin, Weibin; Yan, Zongcheng [Applied Catalysis A: General, 2011, vol. 392, # 1-2, p. 233 - 237]
[9]Location in patent: experimental part Tavakoli-Hoseini, Niloofar; Heravi, Majid M.; Bamoharram, Fatemeh F.; Davoodnia, Abolghasem [Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 787 - 792]
[10]Saravanamurugan, Shunmugavel; Riisager, Anders [Catalysis Today, 2013, vol. 200, # 1, p. 94 - 98]
[11]Garcia-Suarez, Eduardo J.; Khokarale, Santosh G.; Van Buu, Olivier N.; Fehrmann, Rasmus; Riisager, Anders [Green Chemistry, 2014, vol. 16, # 1, p. 161 - 166]
[12]Rafiee, Ezzat; Mirnezami, Fakhrosadat [Journal of Molecular Liquids, 2014, vol. 199, p. 156 - 161]
[13]Rafiee, Ezzat; Mirnezami, Fakhrosadat; Kahrizi, Masoud [Journal of Molecular Structure, 2016, vol. 1119, p. 332 - 339]
[14]Rafiee, Ezzat; Mirnezami, Fakhrosadat [Journal of Molecular Structure, 2017, vol. 1130, p. 296 - 302]
[15]Current Patent Assignee: CHINA PETROCHEMICAL CORPORATION - CN106279035, 2017, A Location in patent: Paragraph 0080; 0083
[16]Shinde; Rode [Green Chemistry, 2017, vol. 19, # 20, p. 4804 - 4810]
[17]Kehrer, Matthias; Mehler, Julian; Taccardi, Nicola; Nagengast, Jens; Kadar, Julian; Collias, Dimitris; Dziezok, Peter; Wasserscheid, Peter; Albert, Jakob [ChemSusChem, 2018, vol. 11, # 6, p. 1063 - 1072]
[18]Gao, Song; He, Liang-Nian; He, Xing; Li, Hong-Ru; You, Fei [Beilstein Journal of Organic Chemistry, 2020, vol. 16, p. 351 - 361]
YieldReaction ConditionsOperation in experiment
Pyridin, 4-Hydroxybutansulfonsaeure;
HO-<CH2>4-SO3H-Sulton, Pyridin;
  • 3
  • [ 21876-43-7 ]
  • [ 827320-61-6 ]
YieldReaction ConditionsOperation in experiment
97.6% With sulfuric acid; at 60℃; A mixture of 1 -(4-sulfonylbutyl)pyridinium (0.077 mol) and sulfuric acid (0.07 mol) were heated with stirring at 60C overnight. During this time the solid liquefy, resulting in the formation of 1 -(4-sulfonylbutyl)pyridinium hydrogensulfate as a slighty yellow sticky oil that was dried under vacuum overnight. Yield 97.6%
With sulfuric acid; at 80℃; for 6h; General procedure: A stoichiometric amount of acid (98% H2SO4, >98% TfOH, 95% HNTf2 or >99.5% MsOH, Sigma-Aldrich) was subsequently added drop wise to the respective zwitterion and the mixture stirred at 80 C for 6 h. The obtained viscous ionic liquids were finally purified by extractive washing with diethyl ether and finally dried under reduced pressure (15 mbar, 50 C) overnight. Yields were above 95% for all ILs.
With sulfuric acid; In water; at 60℃; for 3h;Inert atmosphere; General procedure: A mixture of the betaine (1-3, 11 or 12) (10mmol) and the acid (trifluoromethanesulfonic acid, sulfuric acid, or tetrafluoroboric acid (in a 48% water solution) (10mmol) was stirred at 60C for 3h under argon. After being allowed to cool to room temperature, the ionic liquids were washed repeatedly with toluene (3×5ml) and diethylether (3×5ml) and dried in vacuum at 110C to give the products in 97-98% yields.
  • 4
  • [ 21876-43-7 ]
  • 3C9H14NO3S(1+)*Mo12O40P(3-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphomolybdic acid In water at 80℃; for 10h;
  • 5
  • [ 21876-43-7 ]
  • [ 1041196-76-2 ]
YieldReaction ConditionsOperation in experiment
With phosphoric acid at 80℃; for 8h;
14.8 g With phosphoric acid In dichloromethane; water at 60℃; for 4h; [HSO3-BPy]H2PO4: To prepare the IL [HSO3-BPy]H2PO4, HSO3-BPy was prepared first. Toprepare HSO3-BPy, 0.1 mol (13.6 g) 1,4-butane sultone was mixed with 0.1 mol (7.9 g)pyridine in a flask containing 50 mL of acetonitrile. After 24 h of reflux at 80 C, the reactionmixture was cooled to room temperature and a precipitate was observed. The precipitate wascollected by filtration and washed twice with diethyl ether. The resulting white precipitatewas then dried in vacuum at 60 C for 4 h and HSO3-BPy was obtained. Afterward, theaqueous solution containing a stoichiometric amount of phosphoric acid was added dropwiseto 50 mL CH2Cl2 containing 0.05 mol (10.8 g) HSO3-BPy and stirred at 60 °C for 4 h. Theupper viscous liquid is then separated and washed twice with ether. Drying at 100 C for 12 hyielded a colorless viscous liquid (14.8 g) of 94%. The resulting compound was identified tobe IL [HSO3-BPy]H2PO4.
  • 6
  • [ 21876-43-7 ]
  • 4C9H14NO3S(1+)*O40SiW12(4-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dodecatungstosilic acid In water at 80℃; for 10h;
  • 7
  • [ 21876-43-7 ]
  • 3C9H14NO3S(1+)*O40PW12(3-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphotungstic acid In water at 80℃; for 10h;
  • 8
  • [ 21876-43-7 ]
  • [ 1493-13-6 ]
  • 1-(4-sulfonylbutyl)pyridinium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 80℃; for 8h;
at 60℃; for 8h;
In water at 60℃; for 3h; Inert atmosphere; 2.4 Preparation of ionic liquids 4a,b, 5a-c, 6a A mixture of the betaine (1-3, 11 or 12) (10mmol) and the acid (trifluoromethanesulfonic acid, sulfuric acid, or tetrafluoroboric acid (in a 48% water solution) (10mmol) was stirred at 60°C for 3h under argon. After being allowed to cool to room temperature, the ionic liquids were washed repeatedly with toluene (3×5ml) and diethylether (3×5ml) and dried in vacuum at 110°C to give the products in 97-98% yields. 1-(4-sulfobutyl)pyridinium trifluoromethanesulfonate (4a): 1H NMR δ (DMSO-d6) 9.08-9.11 (m, 2H, 2,6-H); 8.58-8.63 (m, 1H, 4-H); 8.14-8.20 (m, 2H, 3,5-H); 4.63 (t, J=7.5Hz, 2H, NCH2); 2.67 (t, J=7.5Hz, 2H, SCH2); 2.02 (quint, J=7.5Hz, 2H, NHCH2CH2); 1.59 (quint, J=7.5Hz, 2H, SCH2CH2). 13C NMR δ (DMSO-d6) 145.5; 144.8; 128.1; 119.7 (quart, J=321Hz); 60.5; 50.3; 29.8; 21.4.
  • 10
  • [ 21876-43-7 ]
  • [ 827320-61-6 ]
YieldReaction ConditionsOperation in experiment
97.6% With sulfuric acid at 60℃; 5 Example 51-(4-sulfonylbutyl)pyridinium hydrogensulfate; A mixture of 1-(4-sulfonylbutyl)pyridinium (0.077 mol) and sulfuric acid (0.07 mol) were heated with stirring at 60° C. overnight. During this time the solid liquefy, resulting in the formation of 1-(4-sulfonylbutyl)pyridinium hydrogensulfate as a slightly yellow sticky oil that was dried under vacuum overnight. Yield 97.6%.
  • 11
  • phosphotungstic acid [ No CAS ]
  • [ 21876-43-7 ]
  • 3C9H14NO3S(1+)*O40PW12(3-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃; for 24h; 2.2. Preparation of PW-based ionic liquid salts General procedure: PW-based ILs were synthesized following the procedure in Scheme 1. As an example for the preparation of compound II, 4-phenyl-pyridine (PhPy) (1.55 g, 0.01 mol) and 1,4-butane sultone (Bs)(1.36 g, 0.01 mol) were dissolved in toluene (10 mL) and stirred at 50 °C for 48 h under nitrogen atmosphere. A white solid zwitterion PhPyBs was formed; it was filtered and washed with ether three times, then dried in a vacuum. The resulting PhPyBs (8.74 g, 0.03 mol)was added to the aqueous solution of H3PW12O40 (PW) (28.8 g,0.01 mol), followed by the stirring of the mixture at room temperature for 24 h. Water was removed in vacuum to give the final product as solid. QBs-PW (I) and PyBs-PW(III) were prepared based on the samemethod using the corresponding starting materials.
In water at 20℃; for 24h; 2.2. Preparation of SO3H-functionalized POM-ILs General procedure: Isoquinoline (Q) (0.01 mol) and 1,4-butane sultone (Bs)(0.01 mol) were mixed and stirred at 50 C for 48 h under nitrogenatmosphere. A white solid zwitterion QBs was formed. Solid wasfiltered and washed with ether three times and dried in a vacuum.The resulting QBs (0.03 mol) was added to the aqueous solution of PMo (0.01 mol), stirred at room temperature for 24 h. Solvent wasevaporated vacuum to give the final solid product (QBs-PMo).PhPyBs-PW, PyBs-PW, QBs-PW and QBs-SiW were prepared basedon the same method using corresponding starting materials (Scheme 1) according to our previously published paper [26].
In water at 20℃; for 24h; 2.2. Preparation of PW-based sulfonated Bronsted acidic IL catalysts General procedure: Isoquinoline (Q) (0.01 mol) and 1,4-butane sultone (Bs)(0.01 mol) were mixed at 50 C. After 3 h, 5 mL toluene was addedand stirred for 48 h under nitrogen atmosphere. A white solidzwitterion, QBs, was formed; it was filtered off and washed withether for three times, then dried in a vacuum. The resulting aqueoussolution of QBs (0.03 mol)was added to the aqueous solution of PW(0.01 mol), followed by the stirring of the mixture at room temperaturefor 24 h. Water was removed in vacuum to give the finalproduct as solid (QBs-PW). PhPyBs-PW and PyBs-PW were preparedbased on the same method with using corresponding startingmaterials (Scheme 1) according to our previously publishedpaper [31,32].
  • 12
  • [ 21876-43-7 ]
  • [ 7664-93-9 ]
  • [ 827320-61-6 ]
  • 13
  • [ 21876-43-7 ]
  • [ 76-05-1 ]
  • 1-(4-sulfonylbutyl)pyridinium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In toluene at 80℃; for 24h;
  • 14
  • [ 21876-43-7 ]
  • 1-(4-sulfobutyl)pyridinium periodate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With periodic acid In water at 80℃; for 36h; 2 Preparation of ionic liquid [HSO3-BPy]IO4 1,4-butane sultone (14. 98 g, 0.1 mol) was slowly added to a solution of pyridine (7 · 91 g, 0.1 mol)The mixture was stirred for 10 h and incubated at 35 ° C until the reactants were converted to a solid, washed thoroughly with ether and dried in an infrared oven.Take the above solid 7. 16g in a three-necked flask,periodic acid (9.12g, 0.04mol) aqueous solution was slowly added and stirred at 80 ° C for 36h. The [HS03-BPy] IO4 acid ionic liquid oxidant was prepared by vacuum steaming.
  • 15
  • [ 21876-43-7 ]
  • 1-(4-butanesulfonic acid)pyridinium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In cyclohexane; water at 69.8℃;
Same Skeleton Products
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