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Chemical Structure| 19075-58-2 Chemical Structure| 19075-58-2

Structure of 19075-58-2

Chemical Structure| 19075-58-2

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Product Details of [ 19075-58-2 ]

CAS No. :19075-58-2
Formula : C9H5BrO2S
M.W : 257.10
SMILES Code : OC(=O)C1=CC2=C(S1)C=C(Br)C=C2
MDL No. :MFCD07371540
InChI Key :CKBBSFOOIOHLPC-UHFFFAOYSA-N
Pubchem ID :13567980

Safety of [ 19075-58-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 19075-58-2 ]

* 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 [ 19075-58-2 ]

[ 19075-58-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 19075-58-2 ]
  • [ 19075-61-7 ]
  • [ 360576-01-8 ]
  • [ 946428-00-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; at 65℃; Preparation 18; 6-Bromobenzothiophene-3-carboxylic acid methyl ester and 6-Bromobenzothiophene-2- carboxylic acid methyl ester; A solution of the mixture of 6-Bromobenzothiophene-3-carboxylic acid and 6- Bromobenzothiophene-2-carboxylic acid (6.5 g, 25.28 mmol) and sulfuric acid (4.65 g, <n="28"/>47.43 mmol) in MeOH (100 niL) is heated to 65 C overnight. A light brown solid is visualized. The solution is cooled to room temperature and the solid formed is filtered off and washed with MeOH to give 5.6 g (83%) of the mixture of: 6-Bromobenzothiophene- 3-carboxylic acid methyl ester and 6-Bromobenzothiophene-2-carboxylic acid methyl ester in a ratio 7:3. ES/MS m/e 272 (M+2).
  • 2
  • [ 360576-01-8 ]
  • [ 19075-58-2 ]
YieldReaction ConditionsOperation in experiment
96% General procedure: The solution of compound 2a or 2b (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wasadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1 M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a or 3b.
96% With potassium hydroxide; In water; for 3.0h;Reflux; General procedure: The solution of compound 2a-2n (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wereadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 x 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a-3n [31,34].
94% Ausgehend von 4.0 g (14.8 mmol) [6-BROM-L-BENZOTHIOPHEN-2-CARBONSaeUREMETHYL-] ester (aus Beispiel 9A) werden nach der allgemeinen Arbeitsvorschrift B 3.55 g (94 % d. Th. ) des gewuenschten Produkts erhalten. 1H-NMR (400 MHz, [DMSO-D6): No. = 13. ]48 (br. [S,] [1H),] 8. 38 (s, [1H),] 8.22 (s, [1H),] 7.96 (d, 1H), 7.63 [(M,] 1H). HPLC (Methode [1)] : Rt = 4.5 min.
93.5% A solution of 4.0 g (14.8 mmol) of <strong>[360576-01-8]methyl 6-bromo-1-benzothiophene-2-carboxylate</strong> in 40 ml of a 1:1 mixture of THF and 2 N potassium hydroxide solution is stirred at room temperature for 2 h. The solvent is removed in vacuo, and the residue is acidified with concentrated hydrochloric acid. The resulting precipitate is filtered off with suction, washed with water and dried in vacuo at 50 C. 3.55 g (93.5% of theory) of the desired product are obtained. 1H-NMR (400 MHz, DMSO-d6): delta=13.48 (broad s, 1H), 8.38 (s, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.63 (m, 1H). HPLC (method 1): Rt=4.5 min.
84% LiOH.H20 (1.85g, 44mmol) and water (20mL) were added to a stirred solution of <strong>[360576-01-8]6-bromo-benzo[b]thiophene-2-carboxylic acid methyl ester</strong> (I-25a: 2.4g, 8.85mmol) in THF (25mL) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was concentrated, acidified with 2N HCl, filtered and the residue was washed with n-hexane to afford 1.9g of the product (84% yield).1H NMR (DMSO-D6, 300 MHZ): 814.0-14.03 (b, 1H), 8.4-8.39 (d, 1H), 8.28- 8.1 (d, 1H), 8.18-8.0 (d, 1H), 7.78-7.62 (dd, 1H). LCMS Purity: 99%, m/z = 255.9 (M+l)
272 mg With lithium hydroxide monohydrate; In methanol; water; at 75℃; for 2.0h; A mixture of 300 mg of <strong>[360576-01-8]methyl 6-bromobenzo[b]thiophene-2-carboxylate</strong>, 100 mg of lithium hydroxide monohydrate, 3 ml of water, and 9 ml of methanol was stirred for 2 hours at 75C. The reaction mixture was concentratedunder reduced pressure. Water was added to the residues, and the residue was washed three times with tert-butylmethyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and then extraction was performed threetimes by using chloroform. The collected organic layer was washed with saturated saline, dried over magnesium sulfate,and then concentrated under reduced pressure, thereby obtaining 272 mg of 6-bromobenzo[b]thiophene-2-carboxylicacid (hereinafter, described as a "compound 12 of the present invention"). 1H-NMR (DMSO-D6) delta:13.61 (br s, 1H), 8.38 (d, 1H, J = 1.9 Hz0, 8.11 (s, 1H), 7.95 (d, 1H, J = 8.5 Hz), 7.62 (dd, 1H, J= 8.5, 1.9 Hz).

  • 3
  • [ 67-56-1 ]
  • [ 19075-58-2 ]
  • [ 360576-01-8 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 70℃; for 2.0h; Compound TDI01113-1 (500 mg, 1.95 mmol) was dissolved in anhydrous methanol (20 mL), thionyl chloride(4 mL) was slowly added, and the reaction was performed at 70C for 2 hours. Thin layer chromatography (petroleumether : ethyl acetate=5:1) indicated the reaction was complete. The reaction solution was cooled to room temperature,and concentrated under reduced pressure. The crude product was dissolved in dichloromethane (40 mL), and successivelywashed with saturated aqueous sodium carbonate (50 mL X 2) and saturated brine (50 mL X 2). The organicphase was dried over anhydrous sodium sulfate, filtered, and concentrated to afford compound TDI01113-2 (550 mg,yellow solid, crude product).1HNMR(400 MHz, CDCl3) delta 8.01 (s, 2H), 7.73 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 8.4 Hz, 1H), 3.95 (s, 3H).
With thionyl chloride; at 70℃; for 2.0h; Compound TDI01116-1 (500 mg, 1.95 mmol) was dissolved in anhydrous methanol (20 mL), thionyl chloride (4 mL) was slowly added, and the reaction was performed at 70C for 2 hours. Thin layer chromatography (petroleum ether : ethyl acetate=5:1) indicated the reaction was complete. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The crude product was dissolved in dichloromethane (40 mL), and successively washed with saturated aqueous sodium carbonate (50 mL X 2) and saturated brine (50 mL X 2). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to afford compound TDI01116-2 (550 mg, yellow solid, crude product). 1H NMR (400 MHz, CDCl3) delta 8.01 (s, 2H), 7.73 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 8.4 Hz, 1H), 3.95 (s, 3H).
 

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