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CAS No. : | 26137-08-6 | MDL No. : | MFCD00173839 |
Formula : | C6H5BrO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PEGSJNCGPSIJOX-UHFFFAOYSA-N |
M.W : | 221.07 | Pubchem ID : | 2740074 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.3 |
TPSA : | 54.54 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.89 cm/s |
Log Po/w (iLOGP) : | 2.29 |
Log Po/w (XLOGP3) : | 2.48 |
Log Po/w (WLOGP) : | 2.3 |
Log Po/w (MLOGP) : | 1.69 |
Log Po/w (SILICOS-IT) : | 3.04 |
Consensus Log Po/w : | 2.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.01 |
Solubility : | 0.216 mg/ml ; 0.000975 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.27 |
Solubility : | 0.119 mg/ml ; 0.000537 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.6 |
Solubility : | 0.553 mg/ml ; 0.0025 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.6% | Stage #1: at 20℃; for 0.25 h; Stage #2: With sodium nitrite In water at 0 - 5℃; for 1 h; Stage #3: With hydrogen bromide; copper(I) bromide In water at 60 - 65℃; for 2 h; |
3-amino-2-thiophenecarboxylic acid methyl ester (100 g, 0.6369 mol) was suspended in hydrobromic acid (220 ml), and the mixture was stirred at room temperature for 15 mm. The mixture was cooled to 0-5°C, and sodium nitrite (46.0 g, 0.666 mol) in water (100 ml) was added dropwise below 5°C. The mixture was stirred for lhr, and then was addedto a copper (I) bromide (96.0 g, 0.6692 mol) in hydrobromic acid (260 ml) at room temperature. The resulting mixture was stirred at 60-65°C for 2 hrs. The reaction mixture was diluted with 1200 ml of water while maintaining at 25-30°C by cooling and extracted with two 600 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed two times with 600 ml portions of water, and dried over anhydrous sodiumsulfate. The ethyl acetate was removed by distillation under vacuum at 60°C to give 129.0g (91.6 percent) as a yellow solid, melting point 47°C to 48°C, with 96percent purity by HPLC.‘HNMR (400 MHz, CDC13) 6- Value (ppm): 3.90(s, 0-CR3, 3H), 7.09 (d, 1H), 7.46 (d,1H).13 CNMR (400 MHz, CDC13) 6- Value (ppm): 52.10(1C), 116.96(1C), 127.12(1C),130.61 (1C), 133.63 (1C), 161.0 (1C). Mass: 222.8 [M+1]. |
86% | Stage #1: With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 2 h; Inert atmosphere Stage #2: With hydrogenchloride In water; acetonitrileInert atmosphere |
General procedure: Anhydrous copper bromide (12mmol), tert-butyl nitrite (15mmol), and anhydrous acetonitrile (40mL) were added at 0 oC to a three necked round bottom flask that was equipped with a reflux condenser, addition funnel or solid inlet tube, and a gas outlet tube. The coresponding amine (10mmol) in 5mL of acetonitrile or as a solid was slowly added over a period of 5 min to the reaction solution. During this addition, the reaction solution turned completely black from the initial green color and nitrogen was evolved. After gas evolution had been ceased the reaction mixture was stiered at r.t. for 2 hours. Then the mixture was poured into 100 mL of 10percent aqueous hydrochlroic acid and extracted with 100 mL of ether; organic layer was washed once with 100 mL of 10percent aqueous hydrochloric acid. The resulting ether solution was dried over anhydrous Na2SO4 and the ether was removed under reduce prussure. The product was then purified by silca gel column chromatography. |
75% | With tert.-butylnitrite; copper(I) bromide In acetonitrile | Copper bromide (6.7 g, 30.0 mmol) and t-butyl nitrite (3.57 ml, 30 mmol) were dissolved in acetonitrile (40 ml) A solution of methyl 3-amino-2-carboxylate (3.14 g, 20.0 mmol) After overnight reaction at room temperature, Then heated to 60 ° C for 1 hour, After completion of the reaction, cooled to room temperature, quenched by the addition of 2N HC1, add water, extracted with ethyl acetate, combined with several layers, dried and evaporated to dryness, the product was purified by a rapid preparative column 3.32g, yield 75percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride; sulfuric acid In 1,4-dioxane for 24 h; Reflux | A mixture of S-bromo-thiophene-l-carboxylic acid (2.2g, lO.βmmol), 4N HCl (in dioxane, ImI), H2SO4 (98percent, 0.2ml) and methanol (30ml) was heated under reflux for 24h, cooled to room temperature, diluted with ethyl acetate, washed withwater, aq. NaHCO3, half- sat.-aq. NaCl twice, dried (MgSO4) and concentrated to dryness to give compound 23G (100percent) directly used in next step. |
87% | for 12 h; Reflux | By refluxing 3-bromothiophene-2-carboxylic acid and trimethylsilyl chloride (TMSCI) in a methanol solvent for 12 hours, 3-bromothiophene-2-carboxylic acid methylester was prepared. Yield: 87percent White solid 1H-NMR (400 MHz, CDCl3) δ 7.46(d, J=5.2 Hz, 1H), 7.10(d, J=5.2 Hz, 1H), 3.90(s, 3H) |
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