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Chemical Structure| 343790-65-8 Chemical Structure| 343790-65-8

Structure of 343790-65-8

Chemical Structure| 343790-65-8

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Product Details of [ 343790-65-8 ]

CAS No. :343790-65-8
Formula : C9H9NO2S
M.W : 195.24
SMILES Code : COC1=CC=CC(OC)=C1N=C=S
MDL No. :MFCD00046792

Safety of [ 343790-65-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H315-H319-H334-H335
Precautionary Statements:P501-P261-P270-P271-P264-P280-P284-P302+P352-P342+P311-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P304+P340+P312-P403+P233-P405
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 343790-65-8 ]

* 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 [ 343790-65-8 ]

[ 343790-65-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 463-71-8 ]
  • [ 2734-70-5 ]
  • [ 343790-65-8 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 1.16667h;Cooling with ice; To a mixed solution of dichloromethane (500 mL) and water (500 mL) , 2 , 6-dimethoxyaniline (75.8 g, 495 mmol) and sodium hydrogen carbonate (83.1 g, 990 mmol) were added, and thiophosgene (62.6 g, 544 mmol) was added in small portions with stirring under ice cooling. The mixture was stirred for 10 minutes under ice cooling and then stirred at room temperature for 1 hour. An organic layer was separated, and dichloromethane was added to the aqueous layer to extract organic matter. The organic layers were combined, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, n-hexane was added to the obtained solid, and the resulting solid was collected by filtration to obtain the title compound (88.5 g, 454 mmol, 92%) as a white solid. 1H-NMR (400 MHz, CDC13) δ (ppm) : 3.89 (6H, s), 6.54 (2H, d, J = 8.5 Hz), 7.14 (1H, t, J = 8.5 Hz). MS (APCI): m/z 182 [M+H]+.
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; 2-isothiocyanato-1,3-dimethoxybenzene, Example 1.0. To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was evaporated under reduced pressure and the residue was purified on silica gel to provide the title compound 1.0, 2-isothiocyanato-1,3- dimethoxybenzene as white solid (1.06 g, 2.80 mol, 86%). LCMS (ESI pos. ion) mlz:196 (M+H). ‘H NMR (400 MI-Tz, CDC13) 7.16 (t, J 8.48 Hz, 1H), 6.55 (d, J 8.48 Hz, 2H), 3.90 (s, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; 2-Isothiocyanato-1,3-dimethoxybenzene, Example 10.0 To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-Lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C. (internal temperature) and CSCl2 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was then evaporated under reduced pressure and the material thus obtained was purified by SiO2 column to provide Example 10.0, 2-isothiocyanato-1,3-dimethoxybenzene, as a white solid (1.06 g, 2.80 mol, 86%). LCMS (ESI pos ion) m/z: (M+H)+=196. 1H NMR (400 MHz, CDCl3) δ 7.16 (t, J=8.48 Hz, 1H), 6.55 (d, J=8.48 Hz, 2H), 3.90 (app s, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSCl2(374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated under reduced pressure, and the material thus obtained was purified by silica column to provide the title compound, 2- isothiocyanato-1,3-dimethoxybenzene, Example 465.0 as a white solid (1.06g, 2.80 mol, 86%).1H NMR (400 MHz, CDCl3) δ 7.16 (t, J = 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H). LCMS (ESI pos. ion) m/z: (M+H)+196.
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSCl2 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was evaporated under reduced pressure and the initial product was purified by SiO2 column to provide the title compound, 2-isothiocyanato-1,3- dimethoxybenzene, Example 1.2 as white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+H)+ = 196. 1H NMR (400 MHz, CDCl3) δ 7.16 (t, J = 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated under reduced pressure and the material thus obtained was purified by SiC column to provide the title compound, 2-isothiocyanato-l,3-dimethoxybenzene, Example 82.0 as a white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+H)+ = 196. NMR (400 MHz, CDCI3) δ 7.16 (t, J= 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h;Inert atmosphere; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated in vacuo and the initial mass was purified by Si02 column to provide the title compound, Example 372.0, as a white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+1)+ = 196. 1HNMR (400 MHz, CDC13) ö 7.16 (t,J= 8.48 Hz, 1H), 6.55 (d,J= 8.48 Hz, 2H), 3.90 (m, 6H).
53% With sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20℃; for 1.16667h; To a mixture of dichloromethane (50 mL) and water (50 mL) were added 2,6- dimethoxyaniline (4.6 g, 30 mmol, 1 equiv) and sodium bicarbonate (5.0 g, 60 mmol, 2 equiv). Then thiophosgene (2.6 mL, 33 mmol, 1.1 equiv) was added in small portions with stirring at 0C. After addition, the mixture was stirred for 10 mins at 0C and then at room temperature for 1 hour. The organic layer was separated and the aqueous layer was extracted with DCM (2*50 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluted with PE/EtOAc = 200/1) to afford the title compound 2-isothiocyanato-l,3-dimethoxybenzene as an off-white solid (3.1 g, 53% yield). NMR (400 MHz, DMSO-de) d: 7.29 (t, J = 8.0 Hz, 1H), 6.76 (d, J = 8.0 Hz, 2H), 3.86 (s, 6H). LC-MS: m/z 196.1 (M+H)+
With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was then evaporated in vacuo, and the initial mass was purified by Si02 column to provide 2-isothiocyanato-1,3- dimethoxybenzene, Example 28.0 as white solid. LCMS-ESI (pos.) m/z: (M+H) = 196. 1H NMR (400 MHz, CDC13) ö 7.16 (t, J= 8.48 Hz, 1H), 6.55 (d, J= 8.48 Hz, 2H), 3.90 (app s, 6H).

  • 2
  • [ 1520-70-3 ]
  • [ 855784-42-8 ]
  • [ 343790-65-8 ]
  • (Z)-N'-(2,6-dimethoxyphenyl)-2-(6-methoxypicolinoyl)-N-(methylsulfonyl)hydrazinecarboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% (Z)-N?-(2,6-dimethoxyphenyl)-2-(6-methoxypicolinoyl)-N- (methylsulfonyl)hydrazinecarboximidamide, Example 5.01. To a solution of 2- isothiocyanato-1,3-dimethoxybenzene (Example 1.0, 3.90 g, 20.0 mmol) and ethyl sulfonamide (1.81 mL, 21.0 mmol) in ACN (100 mL) at ambient temperature, was added cesium carbonate (8.46 g, 26.0 mmol) in one portion. The reaction was stirred over the weekend. To the mixture was added 6-methoxypicolinohydrazide (3.51 g, 21.0 mmol) in one portion followed by silver(I) nitrate (6.79 g, 40.0 mmol). The mixture was stirred for 15 mm. The material obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0-100percent B/A (B = 15percent MeOWDCM, A = DCM), to provide the title compound 5.01 (8.22 g, 18.8 mmol, 94percent yield) as an off-white powder. LCMS-ESI (POS.) m/z: 438.2 (M+H).
  • 3
  • [ 1520-70-3 ]
  • [ 304665-45-0 ]
  • [ 343790-65-8 ]
  • (Z)-N'-(2,6-dimethoxyphenyl)-N-(ethylsulfonyl)-2-(1-methyl-1H-pyrazole-3-carbonyl)hydrazinecarboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% To a solution of 2- isothiocyanato-1,3-dimethoxybenzene (Example 465.0, 1.97 g, 10.1 mmol) and <strong>[1520-70-3]ethanesulfonamide</strong> (1 g, 9.2 mmol) in ACN (18 mL), was added cesium carbonate (3.88 g, 11.9 mmol). The reaction was stirred at RT for 16 h. To the reaction mixture was added silver(I) nitrate (3.11 g, 18.3 mmol) and then 1-methyl-1H-pyrazole-3- carbohydrazide (1.28 g, 9.2 mmol). Stirring was continued for 10 min at RT. The reaction was then filtered through a plug of silica gel and concentrated in vacuo to give (Z)-N'-(2,6-dimethoxyphenyl)-N-(ethylsulfonyl)-2-(1-methyl-1H-pyrazole-3- carbonyl)hydrazinecarboximidamide (3.76 g, 100 percent yield). To a solution of (Z)-N'-(2,6- dimethoxyphenyl)-N-(ethylsulfonyl)-2-(1-methyl-1H-pyrazole-3- carbonyl)hydrazinecarboximidamide (3.76 g, 9.2) in 1,4-dioxane (92 mL) was added TFA (4.23 mL, 55.0 mmol). The reaction was stirred at 90 °C for 16h. The reaction was concentrated in vacuo, neutralised with an aqueous solution of sodium bicarbonate, and then extracted with EtOAc. After concentration in vacuo,the residue was purified on silica gel (0-50percent) EtOAc/EtOH (3/1) in heptanes to give Example 350.1 (2 g, 56 percent yield).
 

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