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Chemical Structure| 7459-72-5 Chemical Structure| 7459-72-5

Structure of 7459-72-5

Chemical Structure| 7459-72-5

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Product Details of [ 7459-72-5 ]

CAS No. :7459-72-5
Formula : C5H8O3S
M.W : 148.18
SMILES Code : C=CS(=O)(OCC=C)=O
MDL No. :MFCD28361099

Safety of [ 7459-72-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 7459-72-5 ]

* 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 [ 7459-72-5 ]

[ 7459-72-5 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 7459-72-5 ]
  • [ 21806-61-1 ]
YieldReaction ConditionsOperation in experiment
92% Grubbs catalyst first generation; In dichloromethane; for 2h;Heating / reflux;Product distribution / selectivity; Preparation of 6-(aminomethyl)-3,4-dimethylcyclohex-3-ene-1-sulfonic acid (Compound N1); To a cold (-40 C.) solution of allyl alcohol (20 ml, 300 mmol) and NEt3 (26 mL, 186 mmol) in THF (150 mL) was added dropwise 2-chloroethanesulfonyl chloride (10.4 mL, 100 mmol). The reaction was stirred at -40 to -20 C. for 5 hours, quenched with HCl (1M) and extracted with EtOAc. The organic layer was washed with water and dried over Na2SO4. The product was purified by column chromatography using Hexanes/EtOAc 80/20 as eluant to afford allyl vinylsulfonate as a yellowish oil (7 g, 47%). 1H NMR (500 MHz, CDCl3) delta 4.55 (m, 2H), 5.34 (m, 2H), 5.85 (m, 1H), 6.06 (d, J=6.0 Hz, 1H), 6.35 (d, J=17.0 Hz, 1H), 6.50 (dd, J=17 & 9.5 Hz, 1H). To a degassed (by Nitrogen bubbling) solution of allyl vinylsulfonate (3 g, 20.24 mmol) in CH2Cl2 (1 L) was added Grubbs Catalyst (170 mg, 0.2 mmol). The reaction was heated at reflux for 2 h then concentrated. The residual material was applied on silica gel column using Hexanes/EtOAc 80/20 to 50/50 as eluant to afford 1,3-prop-1-ene sultone 2.2 g (92%). 1H NMR (500 MHz, CDCl3) delta 5.11 (dd, J=2.2 & 2.2 Hz, 2H), 6.80 (dt, J=6.6 & 2.2 Hz, 1H), 7.00 (dt, J=6.6 & 2.0 Hz, 1H); 3C NMR (125 MHz, CDCl3) delta 72.54, 124.76, 137.04. A mixture of 1,3-propene sultone (1.44 g, 12 mmol), 2,3-dimethyl-1,3-butanediene (9.5 mL, 84 mmol) in 30 mL of toluene was placed in a sealed tube and heated at 150 C. for 15 hours. The solvent was removed and the residual material was applied on silica gel column using Hexanes/EtOAc 80:20 to 70:30 as eluant to afford 700 mg (86%) of the Diels-Alder adduct. 1H NMR (500 MHz, CDCl3) delta 1.62 (s, 3H), 1.66 (s, 3H), 1.88-1.92 (m, 1H), 2.28-2.42 (m, 3H), 3.12-3.18 (m, 1H), 3.48 (q, J=7.6 Hz, 1H), 3.96 (t, J=8.5 Hz, 1H), 4.40 (dd, J=8.50 & 7.25 Hz, 1H). 13C NMR (125 MHz, CDCl3) delta 19.13, 19.25, 27.20, 30.79, 34.18, 53.04, 72.61, 122.70, 123.44. To an ice-cooled solution of NH4OH (28% in water, 22 mL, 168 mmol) in a co-solvent of THF and EtOH (20 mL, v/v=1:1) was added slowly via a syringe pump a solution of the Diels-Alder adduct from step 3 (680 mg, 3.36 mmol). After the addition (2 h), the reaction was stirred for two more hours until TLC indicated complete consumption of the starting material. The solvent was evaporated and the resulting solid was suspended in mixed solvents of EtOH, acetone and ether, heated for 15 minutes and cooled. The solid was collected by filtration, washed with ether and dried, to give the title compound (450 mg, 61%). 1H NMR (500 MHz, D2O) delta 1.49 (s, 3H), 1.52 (s, 3H), 1.86-1.92 (m, 1H), 2.14-2.28 (m, 3H), 2.44-2.49 (m, 1H), 2.80 (dd, J=13.0 & 6.0 Hz, 1H), 3.10-3.16 (m, 1H), 3.27 (dd, J=14.0 & 6.0 Hz, 1H); 13C NMR (125 MHz, D2O) delta 18.02, 18.28, 28.93, 32.36, 34.69, 38.79, 57.85, 123.09, 123.72. ES-MS 218 (M-1).
 

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