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Chemical Structure| 1648-99-3 Chemical Structure| 1648-99-3

Structure of 1648-99-3

Chemical Structure| 1648-99-3

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Product Details of [ 1648-99-3 ]

CAS No. :1648-99-3
Formula : C2H2ClF3O2S
M.W : 182.55
SMILES Code : FC(F)(F)CS(=O)(Cl)=O
MDL No. :MFCD00007458
InChI Key :CXCHEKCRJQRVNG-UHFFFAOYSA-N
Pubchem ID :74242

Safety of [ 1648-99-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 1648-99-3 ]

* 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 [ 1648-99-3 ]

[ 1648-99-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 408538-22-7 ]
  • [ 1648-99-3 ]
  • [ 99-76-3 ]
  • [ 84449-80-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dichloromethane; 1-pentyl acetate; acetone; Preparation 3 4-(2-piperidinoethoxy) benzoic acid hydrochloride Into a 50 ml round bottom flask is placed 4.93 g (27.0 mmol) of 2,2,2-trifluoroethanesulfonyl chloride and 25 ml of methylene chloride. The resulting solution is cooled with an ice bath as 3.22 g (24.9 mmol) of 1-piperidinoethanol in 7 ml of methylene chloride is added dropwise. After the addition is complete, the ice bath is removed and the resulting slurry is stirred for about 12 hours. The reaction mixture is concentrated on a rotary evaporator to yield a waxy residue. The solid residue is slurried in 45 ml of amyl acetate and then potassium carbonate (5.50 g, 39.9 mmol) and methyl 4-hydroxybenzoate (2.26 g, 14.8 mmol) are added. The resulting mixture is heated to 140° C. for 2 hours. The reaction mixture is cooled to room temperature and washed twice with water and the organic layer is extracted with 10.5 ml of 8N hydrochloric acid. The aqueous layer is heated at gentle reflux for 4 hours. The resulting slurry is cooled to 50° C. and 11 ml of acetone is added. The slurry is cooled to 0°-5° C. and stirred for 1 hour. The product is filtered, washed with cold acetone, and dried at 50° C. in vacuo to yield 3.94 g of product, (90percent).
With potassium carbonate; In dichloromethane; 1-pentyl acetate; acetone; Example 3 Preparation of 4-(2-piperidinoethoxy) benzoic acid hydrochloride Into a 50 ml round bottom flask is placed 4.93 g (27.0 mmol) of 2,2,2-trifluoroethanesulfonyl chloride and 25 ml of methylene chloride. The resulting solution is cooled with an ice bath as 3.22 g (24.9 mmol) of 1-piperidinoethanol in 7 ml of methylene chloride is added dropwise. After the addition is complete, the ice bath is removed and the resulting slurry is stirred for about 12 hours. The reaction mixture is concentrated on a rotary evaporator to yield a waxy residue. The solid residue is slurried in 45 ml of amyl acetate and then potassium carbonate (5.50 g, 39.9 mmol) and methyl 4-hydroxybenzoate (2.26 g, 14.8 mmol) are added. The resulting mixture is heated to 140°C for 2 hours. The reaction mixture is cooled to room temperature and washed twice with water and the organic layer is extracted with 10.5 ml of 8 N hydrochloric acid. The aqueous layer is heated at gentle reflux for 4 hours. The resulting slurry is cooled to 50°C and 11 ml of acetone is added. The slurry is cooled to 0-5°C and stirred for 1 hour. The product is filtered, washed with cold acetone, and dried at 50°C in vacuoto yield 3.94 g of product, (90percent).
  • 2
  • [ 1648-99-3 ]
  • [ 84832-02-0 ]
  • methyl 2,6-difluoro-3-(2,2,2-trifluoroethylsulfonamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.6% With pyridine; In dichloromethane;Cooling with acetone-dry ice; 2,2,2-Trifluoroethyl-sulfonyl chloride (459 mL, 4.15 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (311 g, 1.66 mmol) and pyridine (0.806 mL, 9.97 mmol) in dichloromethane (8.92 mL, 139 mmol), while applying external cooling using an acetone dry ice bath. The reaction mixture was stirred for 45 minutes, and the dry ice bath was removed. The reaction mixture was kept stirring for another hour. The mixture was diluted with EtOAc (100 mL), washed with water (2 X 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and then concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% EtOAc/hexane to afford methyl 2,6-difluoro-3-(2-trifluoroethylsulfonamido) benzoate as a solid (513 mg, 92.6% yield). 1H NMR (400 MHz, d6-DMSO) δ 8.10-8.01 (m, IH), 7.48 (t, IH), 4.68 (s, 2H), 4.58 (s, 2H), 3.98 (s, 3H).
92.6% With pyridine; In dichloromethane;Cooling with acetone-dry ice; 2,2,2-Trifluoroethyl-sulfonyl chloride (459 mL, 4.15 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (311 g, 1.66 mmol) and pyridine (0.806 mL, 9.97 mmol) in dichloromethane (8.92 mL, 139 mmol), while applying external cooling using an acetone dry ice bath. The reaction mixture was stirred for 45 minutes, and the dry ice bath was removed. The reaction mixture was kept stirring for another hour. The mixture was diluted with EtOAc (100 mL), washed with water (2 X 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and then concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% EtOAc/hexane to afford methyl 2,6-difluoro-3-(2-trifluoroethylsulfonamido) benzoate as a solid (513 mg, 92.6% yield). 1H NMR (400 MHz, d6-DMSO) δ 8.10-8.01 (m, IH), 7.48 (t, IH), 4.68 (s, 2H), 4.58 (s, 2H), 3.98 (s, 3H).
  • 3
  • [ 1648-99-3 ]
  • [ 84832-02-0 ]
  • [ 1186194-17-1 ]
YieldReaction ConditionsOperation in experiment
92.6% With pyridine; In dichloromethane; for 0.75h;Cooling with acetone-dry ice; [00210] Step A: 2,2,2-Trifluoroethyl-sulfonyl chloride (459 mL, 4.15 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (311 g, 1.66 mmol) and pyridine (0.806 mL, 9.97 mmol) in dichloromethane (8.92 mL, 139 mmol), while applying external cooling using an acetone dry ice bath. The reaction mixture was stirred for 45 minutes, and the dry ice bath was removed. The reaction mixture was kept stirring for another hour. The mixture was diluted with EtOAc (100 mL), washed with water (2 X 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and then concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% EtOAc/hexane to afford methyl 2,6-difluoro-3-(2- trifluoroethylsulfonamido) benzoate as a solid (513 mg, 92.6% yield). 1H NMR (400 MHz, (CD3)2SO) δ 8.10-8.01 (m, IH), 7.48 (t, IH), 4.68 (s, 2H), 4.58 (s, 2H), 3.98 (s, 3H).
92.6% With pyridine; In dichloromethane; for 1.75h;Cooling with acetone-dry ice; Step A: 2,2,2-Trifluoroethyl-sulfonyl chloride (459 mL, 4.15 mmol) was slowly added to a solution of <strong>[84832-02-0]methyl 3-amino-2,6-difluorobenzoate</strong> (311 g, 1.66 mmol) and pyridine (0.806 mL, 9.97 mmol) in dichloromethane (8.92 mL, 139 mmol), while applying external cooling using an acetone dry ice bath. The reaction mixture was stirred for 45 <n="50"/>minutes, and the dry ice bath was removed. The reaction mixture was kept stirring for another hour. The mixture was diluted with EtOAc (100 mL), washed with water (2 X 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and then concentrated to an oil. The crude product was purified by column chromatography, eluting with 15% EtOAc/hexane to afford methyl 2,6-difluoro-3-(2-trifluoroethylsulfonamido) benzoate as a solid (513 mg, 92.6% yield). 1H NMR (400 MHz, d6-DMSO) δ 8.10-8.01 (m, IH), 7.48 (t, IH), 4.68 (s, 2H), 4.58 (s, 2H), 3.98 (s, 3H).
 

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