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Chemical Structure| 1593-60-8 Chemical Structure| 1593-60-8

Structure of 1593-60-8

Chemical Structure| 1593-60-8

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Product Details of [ 1593-60-8 ]

CAS No. :1593-60-8
Formula : C7H9NO3S
M.W : 187.22
SMILES Code : O=S(C1=CC=C(C)C=C1)(NO)=O
MDL No. :MFCD11850835
InChI Key :XMJJPCJUQLGGND-UHFFFAOYSA-N
Pubchem ID :10081163

Safety of [ 1593-60-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H228
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313
Class:4.1
UN#:1325
Packing Group:

Application In Synthesis of [ 1593-60-8 ]

* 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 [ 1593-60-8 ]

[ 1593-60-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 98-59-9 ]
  • [ 1593-60-8 ]
YieldReaction ConditionsOperation in experiment
87.5% With hydroxylamine hydrochloride; magnesium oxide; In tetrahydrofuran; methanol; water; at 20℃; Hydroxylamine hydrochloride (7.2 g, 86 mmol) was dissolved in methanol (30 ml) and water (20 ml), magnesium oxide (5.1 g, 129 mmol) was added, stirred for 10 minutes, then p-toluenesulfonyl chloride (8 g, 43 mmol) in tetrahydrofuran (300 ml), stirred vigorously at room temperature, and reacted to TLC to monitor the starting material for complete reaction. The extract was filtered through Celite, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-hydroxy-4-methylbenzenesulfonamide (7 g, white solid) in 87.5% yield.
  • 2
  • C26H23NO3S [ No CAS ]
  • [ 1593-60-8 ]
  • 3
  • [ 100-42-5 ]
  • [ 1593-60-8 ]
  • [ 1377813-85-8 ]
  • 4
  • [ 1073-67-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-86-9 ]
  • 5
  • [ 637-69-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-95-0 ]
  • 6
  • [ 826-74-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-99-4 ]
  • 7
  • [ 6380-23-0 ]
  • [ 1593-60-8 ]
  • [ 1377813-97-2 ]
  • 8
  • [ 7315-32-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-98-3 ]
  • 9
  • [ 100-13-0 ]
  • [ 1593-60-8 ]
  • [ 1377813-94-9 ]
  • 10
  • [ 405-99-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-90-5 ]
  • 11
  • [ 2039-82-9 ]
  • [ 1593-60-8 ]
  • [ 1377813-89-2 ]
  • 12
  • [ 3435-51-6 ]
  • [ 1593-60-8 ]
  • [ 1377813-93-8 ]
  • 13
  • [ 402-50-6 ]
  • [ 1593-60-8 ]
  • [ 1377813-92-7 ]
  • 14
  • [ 394-46-7 ]
  • [ 1593-60-8 ]
  • [ 1377813-91-6 ]
  • 15
  • [ 2039-85-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-87-0 ]
  • 16
  • [ 2039-87-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-88-1 ]
  • 17
  • [ 1593-60-8 ]
  • [ 768-03-6 ]
  • [ 1377814-01-1 ]
  • 18
  • [ 1262863-78-4 ]
  • [ 1593-60-8 ]
  • N-hydroxy-4-methyl-N-[3-phenyl-1-(1-tosyl-1H-indol-3-yl)prop-2-ynyl]benzenesulfonamide [ No CAS ]
  • 19
  • [ 1369593-22-5 ]
  • [ 1593-60-8 ]
  • N-hydroxy-N-[1-(4-methoxyphenyl)hex-2-ynyl]-4-methylbenzenesulfonamide [ No CAS ]
  • 20
  • [ 1593-60-8 ]
  • 1-phenylnon-2-yn-1-ol [ No CAS ]
  • N-hydroxy-4-methyl-N-(1-phenylnon-2-ynyl)benzenesulfonamide [ No CAS ]
  • 21
  • [ 1817-49-8 ]
  • [ 1593-60-8 ]
  • [ 1415035-26-5 ]
YieldReaction ConditionsOperation in experiment
38% With iodine; In dichloromethane; water; at 25℃; for 3h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.400.0971.
  • 22
  • [ 1593-60-8 ]
  • [ 73502-43-9 ]
  • [ 1415035-11-8 ]
YieldReaction ConditionsOperation in experiment
46% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 2h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.
  • 23
  • [ 5876-69-7 ]
  • [ 1593-60-8 ]
  • [ 1415035-18-5 ]
YieldReaction ConditionsOperation in experiment
27% With iodine; In dichloromethane; water; at 25℃; for 2h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.
  • 24
  • [ 1522-13-0 ]
  • [ 1593-60-8 ]
  • [ 1415035-12-9 ]
YieldReaction ConditionsOperation in experiment
53% With iodine; In dichloromethane; water; at 25℃; for 4h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.
  • 25
  • [ 1522-13-0 ]
  • [ 1593-60-8 ]
  • [ 1415035-27-6 ]
YieldReaction ConditionsOperation in experiment
48% With N-Bromosuccinimide; ytterbium(III) triflate; In dichloromethane; at 25℃; for 0.5h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) N-tosyl hydroxylamine 2 (0.5 mmol), and NBS (0.6 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at 25 C for 0.5 h. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 6.
  • 26
  • [ 1522-13-0 ]
  • [ 1593-60-8 ]
  • [ 1415034-97-7 ]
YieldReaction ConditionsOperation in experiment
82% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.
  • 27
  • [ 1593-60-8 ]
  • [ 548796-81-2 ]
  • [ 1415034-99-9 ]
YieldReaction ConditionsOperation in experiment
57% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 2h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.
  • 28
  • [ 1593-60-8 ]
  • [ 548796-81-2 ]
  • [ 1415035-13-0 ]
YieldReaction ConditionsOperation in experiment
41% With iodine; In dichloromethane; water; at 25℃; for 2h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.
  • 29
  • [ 1719-18-2 ]
  • [ 1593-60-8 ]
  • [ 1415035-00-5 ]
YieldReaction ConditionsOperation in experiment
70% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.
  • 30
  • [ 1719-18-2 ]
  • [ 1593-60-8 ]
  • [ 1415035-14-1 ]
YieldReaction ConditionsOperation in experiment
47% With iodine; In dichloromethane; water; at 25℃; for 4h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.
  • 31
  • [ 1593-60-8 ]
  • [ 408526-00-1 ]
  • [ 1415035-01-6 ]
YieldReaction ConditionsOperation in experiment
81% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.
  • 32
  • [ 1593-60-8 ]
  • [ 408526-00-1 ]
  • [ 1415035-15-2 ]
YieldReaction ConditionsOperation in experiment
52% With iodine; at 25℃; for 4h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.
  • 33
  • [ 1593-60-8 ]
  • [ 408526-00-1 ]
  • [ 1415035-28-7 ]
YieldReaction ConditionsOperation in experiment
47% With N-Bromosuccinimide; ytterbium(III) triflate; In dichloromethane; at 25℃; for 0.5h; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) N-tosyl hydroxylamine 2 (0.5 mmol), and NBS (0.6 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at 25 C for 0.5 h. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 6.
  • 34
  • [ 62698-34-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-02-7 ]
YieldReaction ConditionsOperation in experiment
86% With ytterbium(III) triflate; In dichloromethane; for 3h;Reflux; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.
  • 35
  • [ 62698-34-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-16-3 ]
YieldReaction ConditionsOperation in experiment
56% With iodine; In dichloromethane; water; for 12h;Reflux; General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.
 

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