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CAS No. : | 41337-81-9 | MDL No. : | MFCD09750009 |
Formula : | C9H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CDFOARSBQKJGNL-UHFFFAOYSA-N |
M.W : | 181.19 g/mol | Pubchem ID : | 10921141 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
89% | Stage #1: With sodium hydroxide In methanol; water at 20℃; for 1 h; Stage #2: With hydrogenchloride In methanol; water |
6-Hydroxymethyl-pyridine-2-carboxylic acid ethylester (200 mg, 1.1 mmol) (J. Amer. Chem. Soc, 1982, 104,2251-2257) was dissolved in methanol (1 ml). Thereafter, therein 2N NAOH aqueous solution (1 ml) was slowly added dropwise, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was acidified (pH=3) with 2N HC1. Solvent was concentrated under reduced pressure, then, dissolved in methanol and filtered. The filtrate was concentrated under reduced pressure to give 150 mg (yield: 89percent, white solid) of the target compound. 1H NMR (400MHZ, CD30D) : 55. 05 (s, 2H), 8.34 (d, J=8. OHZ, 1H), 8.47 (d, J=8. OHZ, 1H) 8.73 (d, J=8. OHz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium tetrahydroborate In tetrahydrofuran for 2h; Reflux; | |
83% | With sodium tetrahydroborate In ethanol at 20℃; | |
69% | With sodium tetrahydroborate In ethanol at -20℃; for 48h; |
62% | With sodium tetrahydroborate In ethanol | |
61.3% | With sodium tetrahydroborate In ethanol at 80℃; for 16h; | |
49% | With sodium tetrahydroborate In ethanol Heating; | |
47% | With sodium tetrahydroborate In ethanol | |
41% | With sodium tetrahydroborate In ethanol for 2h; Reflux; Inert atmosphere; | A001.1 2,6-Pyridine dicarboxylic acid diethyl eater (27.9 g, 0.125 mol) and NaBH4 (3.8 g, 0.1 mol) were dissolved in dry THF (250 mL) and refluxed for 2 h under moisture protection. The solvent was removed and water (50 mL) was added. After stirring for 10 mm, the mixture was extracted with EA (200 mL*2). The organic phases were combined and dried over Mg504, andthe solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel with PE/EA=1:1 to give the product as colorless solid (28 g in 41% yield). ‘H NMR (DMSO-d6) 8.00 (t, 1H, J=7.6 Hz), 7.91 (d, 1H, J7.2 Hz), 7.71 (d, 1H, J7.6 Hz), 5.56 (t, 1H, J=6.0 Hz), 4.62 (d, 2H, J=6.0 Hz), 4.34 (q, 2H, J=7.2 Hz), 1.33 (d, 3H, J=7.2 Hz). |
With sodium tetrahydroborate In ethanol for 2h; Heating; | ||
With sodium tetrahydroborate In ethanol at 50℃; for 4h; | ||
Stage #1: diethyl-2,6-pyridinedicarbonyl ester With sodium tetrahydroborate In ethanol for 19h; Stage #2: With water In dichloromethane | 3.1; 3.2 Ethyl 6-(hvdroxymethyl)-2-pyridinecarboxylate; Reaction 12.28g (60mmol) of sodium borohydride were added to a stirred solution of 22.3g (100mmols) of diethyl 2,6-pyridinedicarboxylate in 200ml of ethanol and stirred for 4 hours then a further 570mg (15mmols) of sodium borohydride was added and stirred for 15 hours. Evaporated, dissolved in 200ml of dichloromethane and washed with 50ml water. Aqueous layer extracted three times with dichloromethane and the combined organics washed with brine. Dried, evaporated, triturated with ether and filtered off to give 13.01 g of white solid; Reaction 2; 11.4g (0.3mol) of sodium borohydride was added in one portion to a stirred solution of111.5g (0.5mol) of diethyl 2,6-pyridinedicarboxylate in 1 litre of ethanol and stirred for 6 hours when a further 2.85g (0.075mol) of sodium borohydride were added and the mixture stirred overnight before being evaporated. The residue was dissolved in 800ml dichloromethane and washed with water. The aqueous was extracted with 4x50ml of dichloromethane. The combined organics were dried, evaporated and combined with the product from reaction 1 (13.1g). The combined material was washed through a pad of silica on a large sinter with ethyl acetate (2 litres) which was evaporated and triturated with ether and filtered off to give 72.6g of a white solid. The MLS (mother liquors) were evaporated and biotaged (chromatographed) [ethyl acetate/hexane (3:1)] to give a further 2.9g of product. | |
With sodium tetrahydroborate In ethanol at 50℃; | ||
With sodium tetrahydroborate; ethanol for 2h; Heating / reflux; | 13 A solution of diethyl 2,6-pyridine dicarboxylate (25 g, 112 mmol) in ethanol (250 mL) was treated with sodium borohydride (2.33 g, 0.55 equiv) and was refluxed for 2 h. After being cooled to RT, the solution was concentrated to a volume of 50 mL and water (50 mL) was added. The solution was further concentrated to a final volume of about 50 mL and extracted with several 50 mL portions of DCM. The combined DCM extracts were dried with sodium sulfate and concentrated by rotary evaporation to yield compound 13A (18.3 g of). HPLC purity 95%. LC/MS m/z 182 (M+H+). | |
26.6 g | With sodium tetrahydroborate In ethanol at 20℃; | |
With sodium tetrahydroborate In ethanol | ||
With sodium tetrahydroborate | ||
With sodium tetrahydroborate; ethanol at 90℃; for 5h; Inert atmosphere; | 1.1 Synthesis of ethyl 6-hydroxymethyl-2-carboxylatepyridine 5 g of ethyl 2,6-dicarboxylate pyridine and 0.424 g of sodium borohydride were added to a round-bottomed flask containing 95 mL of absolute ethanol under nitrogen at a flow rate of 1 mL / s, and 2,6-dicarboxylate The molar ratio of pyridine to sodium borohydride was 1: 0.5. The mixture was refluxed at 90 ° C for 5 h, then adjusted to pH 5, extracted with trichloromethane, dried over anhydrous sodium sulfate, evaporated to remove the chloroform and then mixed with methanol and chloroform at a volume ratio of 1:15 Liquid as the mobile phase and silica gel as the stationary phase to obtain ethyl 6-hydroxymethyl-2-formylpyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | 6-Hydroxymethyl-pyridine-2-carboxylic acid ethylester (200 mg, 1.1 mmol) (J. Amer. Chem. Soc, 1982, 104,2251-2257) was dissolved in methanol (1 ml). Thereafter, therein 2N NAOH aqueous solution (1 ml) was slowly added dropwise, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was acidified (pH=3) with 2N HC1. Solvent was concentrated under reduced pressure, then, dissolved in methanol and filtered. The filtrate was concentrated under reduced pressure to give 150 mg (yield: 89percent, white solid) of the target compound. 1H NMR (400MHZ, CD30D) : 55. 05 (s, 2H), 8.34 (d, J=8. OHZ, 1H), 8.47 (d, J=8. OHZ, 1H) 8.73 (d, J=8. OHz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium(IV) oxide; hydroxylamine hydrochloride 1.) dioxane, reflux, 3 h; 2.) H2O-dioxane, RT, 30 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride | |
100% | With thionyl chloride In dichloromethane at 0℃; for 1.5h; | A001.2 Thoroughly dried 6-(hydroxymethyl) pyridine-2-carboxylic acid ethyl ester (28 g, 154 mmol) was dissolved in DCM (400 mL) was added dropwise of 50C12 (56 mL) at 0°C. After 90 mm the solution was allowed to reach room temperature and the excess of 50C12 was removedunder reduced pressure without heating. DCM (500 mL) was added to the oily residue, and the solution was washed with saturated aqueous of NaHCO3 and dried over Na2504. Evaporation of the solvent afforded 2-(chloromethyl)pyridine-6-carboxylic acid ethyl ester (31 g in 100% yield) as an orange oil. ‘H NMR (DMSO-d6) 8.0 1-8.08 (m, 2H), 7.81 (d, 1H, J=7.2 Hz), 4.86 (s, 2H), 4.37 (q, 2H, J=6.0 Hz), 1.34 (t, 3H, J=7.2 Hz). |
96% | With thionyl chloride at 0℃; for 1h; |
96% | With thionyl chloride at 0℃; | |
91% | With thionyl chloride; sodium carbonate In water | |
85.6% | With thionyl chloride at 0 - 20℃; for 18h; | |
83% | With thionyl chloride at 0℃; for 1.5h; | |
With thionyl chloride In chloroform at 20℃; for 1h; | ||
With thionyl chloride In dichloromethane at 10 - 20℃; for 1.25h; | 3 Ethyl 6-(chloromethyl)-2-pyridinecarboxylate; Thionyl chloride (13.8ml) was added over - 15 minutes to a stirred solution of ethyl 6- (hydroxymethyl)-2-pyridinecarboxylate (28.5g) in MDC (200ml) maintaining the temperature at 10-150C using an ice-water bath. On completion of the addition the mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue partitioned between toluene (200ml)/saturated bicarb (sodium bicarbonate solution, 200ml). The layers were separated and the organic phase washed with water (150ml). The solvent was evaporated to leave a pale oil which solidified on standing. (31.3g). | |
29.5 g | With thionyl chloride In dichloromethane at 10 - 25℃; for 1h; | |
With thionyl chloride In dichloromethane | ||
With thionyl chloride In dichloromethane at 20℃; for 5.5h; Cooling with ice; | 1.2 synthesis of ethyl 6-chloromethyl-2-pyridinecarboxylate 1.81 g of ethyl 6-hydroxymethyl-2-formate pyridine and 730 yL of thionyl chloride were added to a round bottom flask containing 28 mL of dry methylene chloride, 6-hydroxymethyl-2-formylpyridine and The molar ratio of thionyl chloride was 1: 1, stirred for 30 min on an ice bath, and then stirred at room temperature for 5 h. After the completion of the reaction, the methylene chloride was evaporated to dryness, and the toluene was dissolved. The organic layer was washed with water (0.1 m? / L sodium hydrogencarbonate solution) and then the organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to remove 6- Chloromethyl-2-carboxylate pyridine. | |
Stage #1: ethyl 6-(hydroxymethyl)pyridine-2-carboxylate With thionyl chloride In dichloromethane at 10 - 20℃; for 1.25h; Stage #2: With sodium hydrogencarbonate In water; toluene | 1.b Step (b) Ethyl 6-(chloromethyl)-2-pyridinecarboxylate; Thionyl chloride (13.8ml) was added over - 15 minutes to a stirred solution of ethyl 6- (hydroxymethyl)-2-pyridinecarboxylate (28.5g) in MDC (200ml) maintaining the temperature at 10-150C using an ice-water bath. On completion of the addition the mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue partitioned between toluene (200ml)/saturated bicarb (sodium bicarbonate solution, 200ml) The layers were separated and the organic phase washed with water (150ml). The solvent was evaporated to leave a pale oil which solidified on standing (31.3g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 96 percent / SOCl2 / 0 °C 2: 92 percent / dimethylformamide / 20 °C 3: 100 percent / H2NNH2*H2O / ethanol / Heating 4: 67 percent / K2CO3 / acetonitrile / 19 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 96 percent / SOCl2 / 0 °C 2: 92 percent / dimethylformamide / 20 °C 3: 100 percent / H2NNH2*H2O / ethanol / Heating 4: 67 percent / K2CO3 / acetonitrile / 19 h / 80 °C 5: 45 percent / Et3N / [Pd(PPh3)2Cl2] / 17 h / 70 °C / 760 Torr 6: NaOH / methanol; H2O / 17 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 96 percent / SOCl2 / 0 °C 2: 92 percent / dimethylformamide / 20 °C 3: 100 percent / H2NNH2*H2O / ethanol / Heating 4: 67 percent / K2CO3 / acetonitrile / 19 h / 80 °C 5: 45 percent / Et3N / [Pd(PPh3)2Cl2] / 17 h / 70 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / SOCl2 / 0 °C 2: 92 percent / dimethylformamide / 20 °C 3: 100 percent / H2NNH2*H2O / ethanol / Heating | ||
Multi-step reaction with 3 steps 1: 96 percent / SOCl2 / 1 h / 0 °C 2: dimethylformamide / 2 h / Ambient temperature 3: hydrazine / ethanol / Heating | ||
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 1.5 h / 0 °C 2: N,N-dimethyl-formamide / 20 °C 3: hydrazine hydrate / ethanol / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / CHCl3 / 1 h / 20 °C 2: K2CO3 / dimethylformamide / 16 h / 20 °C 3: LiOH / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / CHCl3 / 1 h / 20 °C 2: K2CO3 / dimethylformamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 16 h / 20 °C 2: LiOH / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 100 percent / SOCl2 2.1: K2CO3; KI / acetonitrile / 16 h / Heating 2.2: 32 percent / aq. HCl / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / SOCl2, Na2CO3 / H2O 2: 72 percent / acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / SOCl2, Na2CO3 / H2O 2: 72 percent / acetonitrile 3: 88 percent / acetic acid 4: 95 percent / NaOH / 15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 91 percent / SOCl2, Na2CO3 / H2O 2: 72 percent / acetonitrile 3: 88 percent / acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 24 h 2: 69 percent / NaBH4 / ethanol / 48 h / -20 °C | ||
Multi-step reaction with 2 steps 2: NaBH4 / ethanol / 2 h / Heating | ||
Multi-step reaction with 2 steps 1: ethanol / 16 h / Reflux 2: sodium tetrahydroborate / ethanol / 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / 12 h / Heating 2: toluene / 24 h 3: 69 percent / NaBH4 / ethanol / 48 h / -20 °C | ||
Multi-step reaction with 3 steps 1: SOCl2 / Heating 3: NaBH4 / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 96 percent / SOCl2 / 1 h / 0 °C 2: dimethylformamide / 2 h / Ambient temperature 3: hydrazine / ethanol / Heating 4: 61 percent / triethylamine / CHCl3 5: 60 percent / 1M NaOH / dioxane; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 96 percent / SOCl2 / 1 h / 0 °C 2: dimethylformamide / 2 h / Ambient temperature 3: hydrazine / ethanol / Heating 4: 61 percent / triethylamine / CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) selenium dioxide; 2.) hydroxylamine hydrochloride / 1.) dioxane, reflux, 3 h; 2.) H2O-dioxane, RT, 30 min 2: Et3N / acetonitrile / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1 M OH- / 2 h 2: 20 percent / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1 M OH- / 2 h 2: 50 percent / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1 M OH- / 2 h 2: 50 percent / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride In dichloromethane | |
With thionyl chloride In dichloromethane for 0.5h; | 3.1; 3.2 Ethyl 6-(chloromethyl)-2-pyridinecarboxylate hydrochloride; Reaction 1; 28.56g (0.24mol) of thionyl chloride were added over 5 minutes to a stirred solution of 36.2g (0.2mol) of ethyl 6-(hydroxymethyl)-2-pyridinecarboxylate in dichloromethane (250ml) with water bath cooling and stirred for 30 minutes. Evaporated in vacuo, and re- evaporated with 100ml toluene to give 48g of white oil, which was used immediately; Reaction 2; EPO As for Reaction 1, using 45.14g of ethyl 6-(hydroxymethyl)-2-pyridinecarboxylate and 33g thionyl chloride in 500ml dichloromethane. Yield 59.9g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In methanol; N,N-dimethyl-formamide | 20.1.1 Step 1. Step 1. Synthesis of 6-tert-butyldiphenylsilyloxymethylpyridine-2-carboxylic acid To a solution of 1.8 g of ethyl 6-hydroxymethylpyridine-2-carboxylate in 55 ml of N,N-dimethylformamide, 1.4 g of imidazole and 3.9 g of tert-butyldiphenylsilane chloride were added under cooling with ice, sequentially, followed by stirring for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, water and then brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was dissolved in 60 ml of methanol. To the solution 7.5 ml of 4N aqueous sodium hydroxide solution was added, stirred for 20 hours at room temperature and for further 2 hours at 60° C. Distilling the methanol off under reduced pressure, the residue was made acidic with 1N hydrochloric acid. The system was extracted with chloroform, washed with water and then brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to provide 895 mg of the title compound as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: ethyl 6-(hydroxymethyl)pyridine-2-carboxylate With phosphorus tribromide In dichloromethane at 0℃; for 2h; Stage #2: With sodium hydrogencarbonate In dichloromethane | 13 To a solution of compound 13A (2.86 g, 15.74 mmol) in DCM (100 mL) was added phosphorus tribromide (3.20 g, 11.80 mmol) at 0° C. The solution was stirred for 2 h at 0° C. under nitrogen, then quenched with 100 mL of saturated NaHCO3 solution. The DCM layer was separated, and the aqueous layer was extracted with DCM (3×100 mL). The combined extracts were washed with brine, dried over MgSO4, and evaporated to yield compound 13B (2.65 g). HPLC purity 93%. LC/MS: m/z 244 (M+H). | |
With tetrabutylammomium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 1 h / 10 - 25 °C 2: water; sodium hydroxide / ethanol / 0.17 h 3: aluminum (III) chloride / 6 h / 180 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; sulfuric acid; hydrogen; zinc dibromide / ethyl acetate / 6 h / 65 °C / 1520.1 Torr | ||
Multi-step reaction with 3 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane 2: ethylmagnesium bromide / dichloromethane 3: hydrogen; palladium on activated charcoal; zinc dibromide / ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C | ||
Multi-step reaction with 2 steps 1: sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane 2: ethylmagnesium bromide / dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; sulfuric acid; hydrogen; zinc dibromide / ethyl acetate / 6 h / 65 °C / 1520.1 Torr 4.1: potassium carbonate / ethanol / 2 h / Reflux 5.1: water; sodium hydroxide / ethanol / 70 - 82 °C / Large scale reaction 6.1: water; acetic acid / toluene / 60 - 70 °C | ||
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 1 h / 10 - 25 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; DavePhos / ethanol; toluene / 3 h / 86 °C / Inert atmosphere; Large scale reaction 3.1: water / ethanol / 5 h / Reflux 3.2: 65 - 78 °C | ||
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 1 h / 10 - 25 °C 2: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; DavePhos / ethanol; toluene / 3 h / 86 °C / Inert atmosphere; Large scale reaction 3: water; sodium hydroxide / ethanol / 70 - 82 °C / Large scale reaction 4: water; acetic acid / toluene / 60 - 70 °C |
Multi-step reaction with 5 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: 10% palladium on activated charcoal; sulfuric acid; hydrogen; zinc(II) chloride / ethanol / 14 h / 50 °C 4.1: potassium carbonate / ethanol / 2 h / Reflux 5.1: water / ethanol / 5 h / Reflux 5.2: 65 - 78 °C | ||
Multi-step reaction with 5 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; sulfuric acid; hydrogen; zinc dibromide / ethyl acetate / 6 h / 65 °C / 1520.1 Torr 4.1: potassium carbonate / ethanol / 2 h / Reflux 5.1: water / ethanol / 5 h / Reflux 5.2: 65 - 78 °C | ||
Multi-step reaction with 6 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: 10% palladium on activated charcoal; sulfuric acid; hydrogen; zinc(II) chloride / ethanol / 14 h / 50 °C 4.1: potassium carbonate / ethanol / 2 h / Reflux 5.1: water; sodium hydroxide / ethanol / 70 - 82 °C / Large scale reaction 6.1: water; acetic acid / toluene / 60 - 70 °C | ||
Multi-step reaction with 5 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane 2.1: ethylmagnesium bromide / dichloromethane 3.1: hydrogen; palladium on activated charcoal; zinc dibromide / ethyl acetate 4.1: potassium carbonate / ethanol 4.2: Reflux 5.1: acetic acid / toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; sulfuric acid; hydrogen; zinc dibromide / ethyl acetate / 6 h / 65 °C / 1520.1 Torr 4.1: potassium carbonate / ethanol / 2 h / Reflux 5.1: water; sodium hydroxide / ethanol / 70 - 82 °C / Large scale reaction | ||
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 1 h / 10 - 25 °C 2: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; DavePhos / ethanol; toluene / 3 h / 86 °C / Inert atmosphere; Large scale reaction 3: water; sodium hydroxide / ethanol / 70 - 82 °C / Large scale reaction | ||
Multi-step reaction with 5 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: 10% palladium on activated charcoal; sulfuric acid; hydrogen; zinc(II) chloride / ethanol / 14 h / 50 °C 4.1: potassium carbonate / ethanol / 2 h / Reflux 5.1: water; sodium hydroxide / ethanol / 70 - 82 °C / Large scale reaction |
Multi-step reaction with 4 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane 2.1: ethylmagnesium bromide / dichloromethane 3.1: hydrogen; palladium on activated charcoal; zinc dibromide / ethyl acetate 4.1: potassium carbonate / ethanol 4.2: Reflux | ||
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 1.25 h / 10 - 20 °C 2: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene / 1 - 6 h / 80 - 90 °C 3: ethanol; water / 0.5 h / Heating / reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; sulfuric acid; hydrogen; zinc dibromide / ethyl acetate / 6 h / 65 °C / 1520.1 Torr 4.1: potassium carbonate / ethanol / 2 h / Reflux | ||
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / 10 - 25 °C 2: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; DavePhos / ethanol; toluene / 3 h / 86 °C / Inert atmosphere; Large scale reaction | ||
Multi-step reaction with 4 steps 1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 - 20 °C 2.1: ethylmagnesium bromide / dichloromethane; tert-butyl methyl ether / 0 - 23 °C 2.2: 2 h / 20 °C 3.1: 10% palladium on activated charcoal; sulfuric acid; hydrogen; zinc(II) chloride / ethanol / 14 h / 50 °C 4.1: potassium carbonate / ethanol / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine In dichloromethane at 4 - 20℃; | ||
With sulfur trioxide pyridine complex; dimethyl sulfoxide In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane 2: potassium carbonate; potassium iodide / acetonitrile / 18 h / Inert atmosphere; Reflux 3: water; sodium hydroxide / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 1.5 h / 0 °C 2: sodium phthalimide / N,N-dimethyl-formamide / 2 h / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 2 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 1.5 h / 0 °C 2: sodium phthalimide / N,N-dimethyl-formamide / 2 h / 20 °C 3: triethylamine / dichloromethane / 2 h / 2 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane 2: toluene / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: thionyl chloride / 18 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 16 h / 80 °C 3: trifluoroacetic acid / 22 h / 0 - 20 °C 4: sodium hydroxide / methanol / 12 h / 20 °C / pH 12 5: sodium hydroxide / methanol; water / pH 6 - 6.5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: thionyl chloride / 18 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 16 h / 80 °C 3: trifluoroacetic acid / 22 h / 0 - 20 °C 4: potassium carbonate / acetonitrile / 18 h / 80 °C / Inert atmosphere 5: sodium hydroxide / methanol; water / pH 6 - 6.5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: thionyl chloride / 18 h / 0 - 20 °C 2.1: potassium carbonate / acetonitrile / 16 h / 80 °C 3.1: trifluoroacetic acid / 22 h / 0 - 20 °C 4.1: sodium hydroxide / methanol / 12 h / 20 °C / pH 12 5.1: tin(ll) chloride; citric acid / 0.5 h / 20 °C 5.2: 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 18 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 18 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 16 h / 80 °C 3: trifluoroacetic acid / 22 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 18 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 16 h / 80 °C 3: trifluoroacetic acid / 22 h / 0 - 20 °C 4: sodium hydroxide / methanol / 12 h / 20 °C / pH 12 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 18 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 16 h / 80 °C 3: trifluoroacetic acid / 22 h / 0 - 20 °C 4: potassium carbonate / acetonitrile / 18 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 1.25 h / 10 - 20 °C 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene / 1 - 6 h / 80 - 90 °C 3.1: lithium borohydride / tetrahydrofuran; ethanol / 1 h / 20 °C / Heating / reflux 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: thionyl chloride / dichloromethane / 1.25 h / 10 - 20 °C 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene / 1 - 6 h / 80 - 90 °C 3.1: lithium borohydride / tetrahydrofuran; ethanol / 1 h / 20 °C / Heating / reflux 3.2: 20 °C 4.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / dichloromethane / 1.25 h / 10 - 20 °C 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene / 1 - 6 h / 80 - 90 °C 3.1: lithium borohydride / tetrahydrofuran; ethanol / 1 h / 20 °C / Heating / reflux 3.2: 20 °C 4.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C |
Tags: 41337-81-9 synthesis path| 41337-81-9 SDS| 41337-81-9 COA| 41337-81-9 purity| 41337-81-9 application| 41337-81-9 NMR| 41337-81-9 COA| 41337-81-9 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
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P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
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P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
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P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
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P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
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P285 | In case of inadequate ventilation wear respiratory protection. |
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P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
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P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
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P337 | If eye irritation persists: |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
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P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
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P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
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P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
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P402 | Store in a dry place. |
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P420 | Store away from other materials. |
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P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
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Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
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H220 | Extremely flammable gas |
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H223 | Flammable aerosol |
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H228 | Flammable solid |
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H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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