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Chemical Structure| 103-47-9 Chemical Structure| 103-47-9
Chemical Structure| 103-47-9

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CHES (N-Cyclohexyltaurine) is a zwitterionic buffer that binds to hemagglutinin (HA), mimicking sialic acid (SA) and receptor-binding sites (RBS), and is widely used in neutralizing antibody studies.

Synonyms: N-Cyclohexyltaurine

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of CHES

CAS No. :103-47-9
Formula : C8H17NO3S
M.W : 207.29
SMILES Code : OS(=O)(=O)CCNC1CCCCC1
Synonyms :
N-Cyclohexyltaurine
English Name :N-Cyclohexyltaurine
MDL No. :MFCD00003835
InChI Key :MKWKNSIESPFAQN-UHFFFAOYSA-N
Pubchem ID :66898

Safety of CHES

Application In Synthesis of CHES

* 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 [ 103-47-9 ]

[ 103-47-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 103-47-9 ]
  • [ 85582-50-9 ]
YieldReaction ConditionsOperation in experiment
76%
With phosphorus pentachloride; ammonia; water; trichlorophosphate 1.) 60 deg C, 2.) CHCl3, 10-15 deg C, 24 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 65 percent / PCl5, POCl3 / 90 °C 2: 94 percent / Na2CO3 / ethyl acetate / 48 h / 110 °C
  • 2
  • [ 103-47-9 ]
  • [ 103020-61-7 ]
YieldReaction ConditionsOperation in experiment
65% With phosphorus pentachloride; trichlorophosphate at 90℃;
  • 3
  • [ 103-47-9 ]
  • [ 1444690-54-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile Reflux; As shown in Scheme 4, reaction of TPO chloride (2) with 2- (Cyclohexylamino)ethanesulfonic acid (6) in the presence of K2C03 in acetonitrile under reflux gives water soluble photo initiator IV.
  • 4
  • [ 103-47-9 ]
  • [ 1444690-63-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile Reflux; As shown in Scheme 7, reaction of TPO di-chloride (4) with 2 equivalents of 2-(Cyclohexylamino)ethanesulfonic acid (6) in the presence of K2CO3 in acetonitrile under reflux gives water soluble photo initiator VII.
  • 5
  • [ 108-91-8 ]
  • [ CAS Unavailable ]
  • [ 103-47-9 ]
YieldReaction ConditionsOperation in experiment
10.9 g In water at 50℃; for 6h; Reflux; 2.1; 2.2; 2.3; 2.4 Example 2: A process for synthesizing 2-cyclohexylaminoethanesulfonic acid, comprising the steps of: 1) 99 g (1 mol) of cyclohexylamine was heated to 50 ° C, and then a solution of 181 g (0.98 mol) of sodium 2-chloroethylsulfonate dissolved in 170 mL of water was dissolved by heating, and the mixture was stirred and heated to reflux for 6 hours. ; 2) After the reaction liquid obtained in the step 1) is cooled, 5.5 g of activated carbon is added, and the reflux reaction is complete; 3) The reaction liquid obtained in the step 2) is filtered while hot, the filtrate is concentrated to 48 mL, 200 mL of ethanol is added, and the pH is adjusted to 5.0-6.0 with glacial acetic acid; 35 mL of ethanol is added, cooled to 10 ° C, and filtered; 4) Add the filter residue obtained in step 3) to 280 mL of hot ethanol and heat to reflux.Add 38 mL of water, filter while hot, cool to 10 ° C, and filter.The filtrate was washed with cold ethanol and dried to give 45.0 g (0.182 mol) of 2-cyclohexylaminoethanesulfonic acid with an HPLC purity of 98%; Step 5): The filtrate obtained in the step 4) is concentrated to 170 mL, and filtered.Add the filter residue to 120 mL of hot ethanol, heat to reflux, add 16 mL of water, filter while hot, and cool to 10 ° C.Filtration, the residue was washed with ethanol and dried to give 10.9 g.(0.044 mol) 2-cyclohexylaminoethanesulfonic acid having an HPLC purity of 98%.
  • 6
  • [ 108-91-8 ]
  • [ 107-06-2 ]
  • [ 103-47-9 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: cyclohexylamine With copper; sodium sulfite In ethanol; water Reflux; Stage #2: 1,2-dichloro-ethane In ethanol; water at 65℃; for 3h; 1-3 Example 2 In a 1L three-necked flask with mechanical stirring, first add 300ml of water and 400g of absolute ethanol.Stir evenly, then add 99g (1mol) cyclohexylamine, 5g copper powder,132g (1.05mol) sodium sulfite to form a mixed solution, heat the mixed solution to reflux,Then, 128g (1.3mol) 1,2-dichloroethane was slowly added dropwise, and the dropping time was controlled within 2h,After the dripping is completed, react for 1 hour at the reflux temperature of 65°C to obtain a reaction liquidThe reaction liquid is filtered to remove the catalyst copper powder, and the mother liquor is distilled under reduced pressure.Remove the mixture of ethanol and water, or recycle it for reuse;After the bottom of the distillation kettle is viscous, add 600ml of absolute ethanol to dissolve it.Adjust pH to 5-7 with concentrated hydrochloric acid, cool and crystallize to obtain a crude product,This crude product was rectified to obtain 178 g of refined product N-cyclohexyl-2-aminoethanesulfonic acid, the yield of which was about 86%, and the purity of chromatographic analysis was 99.5%.
  • 7
  • [ 54757-46-9 ]
  • [ 103-47-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: acitretin With triethylamine; isobutyl chloroformate In tetrahydrofuran at 5 - 10℃; Inert atmosphere; Darkness; Stage #2: 2-(cyclohexylamino)ethanesulfonic acid With triethylamine In methanol at 20 - 25℃; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In water 1.1 1.1 Synthesis of compound 1 In a 25 mL two-necked flask, acitretin (250 mg, 0.77 mmol) and TEA (92 pL, 0.91 mmol) were dissolved in anhydrous THF (10 mL) and the mixture was cooled to 5-10 °C. A solution of isobutylchloroformate (129 pL, 0.99 mmol) in THF (0.5 mL) was added dropwise to the chilled solution. The resulting mixture was stirred for 30 minutes at 5-10 °C under inert conditions and protected from light. (0114) A solution of CHES (222 mg, 1.07 mmol) and TEA (149 pL, 1.07 mmol) in methanol (3 mL) was added to the reaction mixture and the resulting solution was stirred under inert conditions at room temperature for 2.5 hours. Acetic acid (200 pL) was then carefully added to the reaction mixture. The solution was evaporated to dryness and the resulting crude was extracted with MTBE (20 mL) and water (25 mL). The layers were separated and the organic layer was discarded. Sodium hydrogencarbonate (300 mg) was added carefully to the aqueous layer. When effervescence had stopped, brine (25% NaCI-solution, 20 mL) was added and the resulting aqueous solution was extracted with ethyl acetate (20 mL). The layers were separated and the aqueous was phase discarded. The organic layer was washed with a mixture of brine (12.5% NaCI-solution, 20 mL) and methanol (2 mL). The aqueous layers were discarded, and the organic layer was evaporated under reduced pressure (40-70 mbar at 39 °C). The release of the vacuum was made with inert gas (N2). The product was washed with MTBE (10 mL) and dried under vacuum. The obtained product was purified by column chromatography (RP-C18; eluent: MeOH/water 7:3) to afford the product as a yellow solid (purity 94.8%). Yield: 50%. (0115) XH NMR (500 MHz, DMSO-d6): 6 6.85 (ddd, 1H, J = 30.2, 15.2, 11.4 Hz, CH=CH-); 6.67 (s, 1H, Ph-H); 6.65 (d, 1H, J = 16.4 Hz, -CH=CH-); 6.42 (dd, 1H, J = 16.4 Hz, -CH=CH-); 6.31 (s, 1H, =C-CH); 6.25-6.19 (m, 2H, -CH=CH-); 3.78 (s, 3H, -O-CH3); 3.45 (m, 2H, CH2); 3.35 (m, 2H, CH2); 2.65 (m, 1H, CH cyclohexyl); 2.50 (s, 3H, CH3); 2.23 (s, 3H, CH3); 2.21 (s, 3H, CH3); 2.12 (s, 6H, CH3);1.9 (S, 3H, CH3); 1.77, (m, a (2H) cyclohexyl); 1.62, (m, e (2H) cyclohexyl); 1.28, (m, a (2H) cyclohexyl); 1.10, (m, e (2H) cyclohexyl); 1.05, (m, 2H, cyclohexyl). m/z = 538.26; 516.27.
 

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