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Chemical Structure| 52665-48-2 Chemical Structure| 52665-48-2

Structure of 52665-48-2

Chemical Structure| 52665-48-2

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Product Details of [ 52665-48-2 ]

CAS No. :52665-48-2
Formula : C4H3ClO3S
M.W : 166.58
SMILES Code : O=S(C1=CC=CO1)(Cl)=O
MDL No. :MFCD06658968
InChI Key :IEKOSPNJXYCZHY-UHFFFAOYSA-N
Pubchem ID :2795072

Safety of [ 52665-48-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 52665-48-2 ]

* 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 [ 52665-48-2 ]

[ 52665-48-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 52665-48-2 ]
  • [ 33084-49-0 ]
  • N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With NaH; EXAMPLE 69 N-(4-Bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide was prepared by the method of Example 1 with 5-amino-4-bromo-3-methyl-isoxazole (0.266 g, 1.5 mmol), NaH (60% oil dispersion) (0.15 g, 3.8 mmol) and furan-2-sulfonyl chloride (Example 36A) (0.30 mg, 1.8 mmol). Flash chromatography (50% EtOAc/hexane) and recrystallization from CHCl3 and hexane provided 90 mg (20% yield) of light yellow crystals (m.p. 117-119 C.).
20% With NaH; EXAMPLE 69 N-(4-Bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide was prepared by the method of Example 1 with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (0.266 g, 1.5 mmol), NaH (60% oil dispersion) (0.15 g, 3.8 mmol) and furan-2-sulfonyl chloride (Example 36A) (0.30 mg, 1.8 mmol). Flash chromatography (50% EtOAc/hexane) and recrystallization from CHCl3 and hexane provided 90 mg (20% yield) of light yellow crystals (m.p. 117-119 C.).
20% With NaH; EXAMPLE 69 N-(4-Bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide was prepared by the method of Example 1 with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (0.266 g, 1.5 mmol), NaH (60% oil dispersion) (0.15 g, 3.8 mmol) and furan-2-sulfonyl chloride (Example 36A) (0.30 mg, 1.8 mmol). Flash chromatography (50% EtOAc/hexane) and recrystallization from CHCl3 and hexane provided 90 mg (20% yield) of light yellow crystals (m.p. 117-119 C.).
  • 2
  • [ 52665-48-2 ]
  • [ 84832-02-0 ]
  • [ 1269421-46-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 16h; Step A: Methyl 3-amino-2,6-difluorobenzoate (652.8 mg, 3.488 mmol) was dissolved in 17.4 mL DCM (0.2 M) and treated sequentially with triethylamine (1.42 mL, 10.46 mmol) and furan-2-sulfonyl chloride (1.162 g, 6.976 mmol). The reaction mixture was stirred at ambient temperature for 16 hours and then diluted with additional DCM and washed with water (2x) and brine (Ix). The organic phase was dried over Na2SO4 and concentrated to provide methyl 2,6- difluoro-3-(N-(furan-2-ylsulfonyl)furan-2-sulfonamido)benzoate (1.561 g, 3.489 mmol). The crude material was then immediately dissolved in 17.5 mL 4:1 THF:MeOH (0.2 M) and treated with 2.0 M KOH (8.7 mL, 17.45 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The organic solvent was removed under reduced pressure and the aqueous residue acidified to pH 3 using 1.0 M HCl. Extraction with EtOAc (2x) was followed by washing the combined organic extracts with water (2x). The crude product was then extracted as its carboxylate salt with 1.0 M NaOH (2x). The combined aqueous NaOH extracts were acidified to pH 3 using 6.0 M HCl and extracted with EtOAc (2x). The combined organic extracts were washed with water (2x) and brine (Ix) and then dried over Na2SO4 and concentrated to afford 2,6-difluoro-3-(furan-2-sulfonamido)benzoic acid (475.0 mg, 1.566 mmol, 44.91% yield). LC/MS: m/z 302.0 [M-I].
With triethylamine; In dichloromethane; at 20℃; for 16h; Methyl 3-amino-2,6-difluorobenzoate (652.8 mg, 3.488 mmol) was dissolved in 17.4 mL dichloromethane (0.2 M) and treated sequentially with triethylamine (1.42 mL, 10.46 mmol) and furan-2-sulfonyl chloride (1.162 g, 6.976 mmol). The reaction mixture was stirred at ambient temperature for 16 hours and then diluted with additional dichloromethane and washed with water (2x) and brine (Ix). The organic phase was dried over Na2SO4 and concentrated to provide methyl 2,6-difluoro-3-(iV-(furan-2-ylsulfonyl)furan-2-sulfonamido)benzoate (1.561 g, 3.489 mmol). The crude material was then immediately dissolved in 17.5 mL 4:1 THF:MeOH (0.2 M) and treated with 2.0 M KOH (8.7 mL, 17.45 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The organic solvent was removed under reduced pressure and the aqueous residue acidified to pH 3 using 1.0 M HCl. Extraction with EtOAc (2x) was followed by washing the combined organic extracts with water (2x). The crude product was then extracted as its carboxylate salt with 1.0 M NaOH (2x). The combined aqueous NaOH extracts were acidified to pH 3 using 6.0 M HCl and extracted with EtOAc (2x). The combined organic extracts were washed with water (2x) and brine (Ix) and then dried over Na2SO4 and concentrated to afford 2,6-difluoro-3-(furan-2-sulfonamido)benzoic acid (475.0 mg, 1.566 mmol, 44.91% yield). LC/MS: m/z 302.0 [M-I].
  • 3
  • [ 52665-48-2 ]
  • [ 84832-02-0 ]
  • C12H9F2NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; Methyl 3-amino-2,6-difluorobenzoate (652.8 mg, 3.488 mmol) was dissolved in 0.2M DCM (17.4 mL), chilled to 0C, and then treated sequentially with triethylamine (1.42 mL, 10.46 mmol) and furan-2-sulfonyl chloride (1.16 mg, 6.98 mmol). The reaction mixture was warmed to ambient temperature and stirred for 16 hours. The reaction mixture was diluted with EtOAc, washed with water (2 X) and brine (1 X), dried over Na2S04, filtered and concentrated. The crude reaction mixture was then dissolved in 4:1 THF:MeOH (17.5 mL) and treated with 2.0M KOH (8.70 mL, 17.45 mmol) at ambient temperature for 2 hours. The organic solvent was then concentrated off in vacuo, and the reaction mixture was diluted with water and extracted with EtOAc (2 X). The aqueous layer was then acidified to pH 3 using 6.0M HC1 and extracted with EtOAc (2 X). The organics were washed with water (2 X) and brine (1 X), dried over Na2S04, filtered and concentrated to afford 2,6-difluoro-3-(furan-2-sulfonamido)benzoic acid (475.0 mg, 1.57 mmol, 44.9% yield). LC MS: m/z 302.0 [M-l].
 

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