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Chemical Structure| 206874-43-3

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CAS No.: 206874-43-3

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Product Details of [ 206874-43-3 ]

CAS No. :206874-43-3
Formula : C9H11NO5S
M.W : 245.25
SMILES Code : CS(=O)(OCCC1=CC=CC([N+]([O-])=O)=C1)=O
MDL No. :MFCD27947153

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Application In Synthesis of [ 206874-43-3 ]

* 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 [ 206874-43-3 ]

[ 206874-43-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 52022-77-2 ]
  • [ 124-63-0 ]
  • [ 206874-43-3 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; 3-Nitrorhohenethyl methanesulfonate can be synthesized by the following procedure. To a solution of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> (17.9 mmol) and triethylamine (23.3 mmol) in DCM (50 mL), is added methanesulfonyl chloride (18.8 mmol) in DCM (10 mL) at 0 0C under a nitrogen atmosphere. After the addition is complete, the reaction is allowed to warm to rt and it is stirred for another 2 h. The solvent is removed and the residue is dissolved in DCM (100 mL). The organic layer is washed with water, dried over Na2SO4 and concentrated to afford 3-nitrophenethyl methanesulfonate (98%) that is used without further purification. MS (m/z) (M+l)+ 246.2.
98% With pyridine; In dichloromethane; at 0 - 20℃; [0439] A solution of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> (9 g, 53.8 mmol) in DCM (100 mL) was cooled to 0 C, then pyridine (22.7 g, 287 mmol) was dropwise added to the reaction solution. Then methylsulfonylchloride was added slowly dropwise, followed by stirring at room temperature for one hour. Water was added to terminate the reaction. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 3-nitrophenethyl methanesulfonate (13 g, yield 98%). 1H NMR: 400 MHz CDC13 delta 8.13-8.10 (m, 2H), 7.60-7.53 (m, 1H), 7.53-7.47 (m, 1H), 4.48-4.45 (m, 2H), 3.19-3.15 (m, 2H), 2.95(s, 3H).
84% With triethylamine; In dichloromethane; at 0 - 20℃; for 5h; Description 4 2- (3-NITROPHENYL) ETHYL METHANESULFONATE (D4); METHANESULFONYL chloride (0. 28 mL) was added dropwise to a stirred solution of 2- (3- nitrophenyl) ethanol (0. 5 g; 1 eq) in DICHLOROMETHANE (3 mL) and triethylamine (0.5 mL; 1.2 eq) at 0C under an inert atmosphere. The solution was allowed to reach r. t. and stirred for 5 hours. The reaction mixture was diluted with water (3 mL) and extracted into DICHLOROMETHANE (3x3 mL). The organic layers were combined, dried over NA2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography, eluting with a gradient from DICHLOROMETHANE to DICHLOROMETHANE/MEOH (98/2) affording the title compound in 84% yield (0.62 g). 'H-NMR (300 MHz, CDCI3) 8 (ppm): 8.15 (m, 2 H), 7.53 (m, 2 H), 4.45 (t, 2 H), 3,15 (t, 2H), 2.92 (s, 3 H).
75% With triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with ice; Dissolve 2- (3-nitrophenyl) ethan-1-ol 1a (100 g, 598 mmol) in 1 L of dichloromethane, add triethylamine (121 g, 1.2 mol, 2 eq) with stirring, and place the reaction solution on ice. Methanesulfonyl chloride (137 g, 1.2 mol, 2 eq) was added dropwise under bath cooling, and the reaction was allowed to proceed for 1 hour at room temperature. 500 mL of water was added and the layers were separated. The aqueous phase was extracted with dichloromethane (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3-nitrophenethyl mesylate. 1b (110 g, 448 mmol, yellow liquid), yield: 75%.
With pyridine; In dichloromethane; at 0℃; for 0.5h; To <strong>[52022-77-2]2-(3-nitrophenyl)ethan-1-ol</strong> in methylene chloride at 0 C. was added methanesulfonylchloride (2 eq) and pyridine (4 eq) and stirred for 30 minutes. The formation of the mesylate was observed on LC/MS. Water was then added and the organic layers was separated and washed with 1M citric acid. The organic layer was dried with sodium sulfate and concentrated. To give the mesylate. The mesylate was taken in tetrahydrofuran and pyrrolidine (4 eq) was added and the mixture was heated to 80 C. for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate and concentrated. It was then passed through a plug of silica to yield [2-(3-nitrophenyl)ethyl]pyrrolidine. [0759] MS: MH+=220.
With pyridine; In dichloromethane; at 0 - 20℃; Step 1. Synthesis of Methanesulfonic acid 2-(3-nitro-phenyl)-ethyl ester To a solution of 2-(3-nitro-phenyl)-ethanol (1 eq) in dichloromethane at 0 C. was added pyridine (4 eq) and methanesulfonyl chloride (2 eq). After stirring at 0 C. for one hour, then room temperature overnight, the mixture was diluted with dichloromethane and washed once with water, once with 1 N HCl, dried with anhydrous sodium sulfate, filtered and concentrated. The product was clean enough to be taken on to the next step without purification. MH+=246.0.
With triethylamine; In dichloromethane; for 2h; A. methanesulfonic acid 2-(3-nitro-phenyl)-ethyl ester To a solution of 5 g of 2-(3-nitro-phenyl)-ethanol and 4.5 mL of triethylamine in 50 mL of dichloromethane was added dropwise 3.7 g of methanesulfonyl chloride, and the reaction was stirred for 2 h. The reaction mixture was washed twice with water, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 6.6 g of the title compound.
With triethylamine; In dichloromethane; at 0℃; for 4h; c.; A solution of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> (175 g, 1.047 moles) in DCM (2L) was treated with Et3N (220 mL, 1.570 moles), cooled to 0 0C, treated with mesyl chloride (99 mL, 1.256 moles), and stirred for 4 hours. The reaction mixture was washed with water (3 x 1 L), brine (2 x 1 L), dried (Na2SO4), filtered and concentrated to a brown liquid (200 g).

  • 2
  • [ 52022-77-2 ]
  • [ 7143-01-3 ]
  • [ 206874-43-3 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In dichloromethane; at 20℃; for 16h; Procedure S: Intermediate 24 (1-24) - 3-Nitrophenethyl methanesulfonate.; [00134] To a solution of 1.6 g (10 mmol, 1.0 eq.) of 2-(3-nitrophenyl) (1-23) in 20 mL of methylene chloride was added 2.8 mL (20 mmol, 2.0 eq.) of triethylamine. A solution of 1.7 g (10 mmol, 1.0 eq.) of methanesulfonic anhydride in 10 mL of methylene chloride was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was washed with sat. brine and the organic layer was dried (Na2SC^). The solvent was removed in vacuo and the resulting residue was purified by flash chromatography to provide 2.2 g (9.0 mmol, 90%) of 3-nitrophenethyl methanesulfonate (1-24).
  • 3
  • [ 206874-43-3 ]
  • [ 1234356-69-4 ]
 

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