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Excepted Quantity | Free |
Inaccessible (Haz class 6.1), Domestic | USD 41.00 |
Inaccessible (Haz class 6.1), International | USD 64.00 |
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CAS No. : | 65996-17-0 | MDL No. : | MFCD16610942 |
Formula : | C9H10BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 244.09 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 | UN#: | 2810 |
Hazard Statements: | H301-H311-H331 | Packing Group: | Ⅲ |
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 |
---|---|---|
In ethanol at 100℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.5% | With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
/BRN= 778458/ (2O), CH3COOH, 30percent HBr-CH3COOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: ethanol / 6 h / 100 °C 2: 1.) DMPU, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min 3: 88percent aq. HCOOH / CH2Cl2 / 2 h / Ambient temperature 4: aq. NaOH / ethanol / 1.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ethanol / 6 h / 100 °C 2: 1.) DMPU, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min 3: 88percent aq. HCOOH / CH2Cl2 / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 6 h / 100 °C 2: 1.) DMPU, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 58 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran / 24 h / Heating 2: 80 percent / polyphosphoric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / Pd(PPh3)4 / tetrahydrofuran / 24 h / Heating 2: 80 percent / polyphosphoric acid | ||
Multi-step reaction with 2 steps 1: 94.5 percent / Pd(PPh3)4 / tetrahydrofuran / 24 h / Heating 2: 80 percent / polyphosphoric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropylamine In tetrahydrofuran; hexane; water; ethyl acetate | 27 (Table D, cpd. no. 523) EXAMPLE 27 Preparation of ethyl 2-bromo-4-[(4,6-dimethoxy-2-pyrimidinyl)methyl]nicotinate (Table D, cpd. no. 523) 7.32 g of ethyl 2-bromo-4-methyl nicotinate and 150 ml of THF are cooled in a dry ice/acetone bath under N2 atmosphere, 30 ml of LDA are added over 5 mins and the mixture stirred for 30 mins. 6.55 g of 2-methylsulphonyl-4,6-dimethoxypyrimidine are added as a solid, rinsing with 50 ml of THF, and the mixture stirred cold for 2 hrs and slowly allowed to warm. The THF is evaporated, ca 75 ml of water added and the mixture extracted three times with methylene dichloride. The combined extracts are evaporated and the residue taken up with 20 ml of 25% ethyl acetate/hexane and flash chromatographed using 2 l of 25% ethyl acetate/hexane in 50 ml fractions. Fractions 7 to 14 are combined, evaporated and placed in a Kugelrohr at ca 105° for 2 hrs. The residue is taken up in 20 ml of 10% ethyl acetate/hexane and flash chromatographed with 2 l 10% ethyl acetate/hexane in 50 ml portions to yield title compound (NMR) in fractions 18 to 32. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.8.4 4. 4. 2-Bromo-4-methyl-3-pyridinecarboxylic Acid 1-Oxide Ethyl Ester Prepared from 2-bromo-4-methyl-3-pyridinecarboxylic acid ethyl ester (for preparation, see Baldwin et al., Journal of Organic Chemistry, 1978, 43, 2529). 1 H NMR (CDCl3): δ 1.39 (3H, t, J=7), 2.29 (3H, s), 4.43 (2H, q, J=7), 7.07 (1H, d, J=7), 8.26 (1H, d, J=7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide for 14h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 14h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In propionic acid for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In propionic acid for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: piperidine; acetic acid / 24 h / 760.05 Torr / Reflux 2.1: ethanol / 6 h / 760.05 Torr / Reflux 3.1: hydrogen bromide; acetic acid / 2 h / 40 - 55 °C / 760.05 Torr 3.2: 760.05 Torr / Cooling with ice | ||
Multi-step reaction with 3 steps 1: piperidine; acetic acid / 24 h / Reflux 2: ethanol / 6 h / Reflux 3: hydrogen bromide; acetic acid / 2 h / 55 °C | ||
Multi-step reaction with 3 steps 1: acetic acid; piperidine / 18 h / 100 °C 2: toluene; acetic anhydride / 18 h / 50 °C 3: acetic acid; hydrogen bromide / 18 h / 55 °C |
Multi-step reaction with 3 steps 1: piperidine; acetic acid / 24 h / 90 °C 2: ethanol / 15 h / 80 °C 3: acetic acid; hydrogen bromide / 15 h / 40 - 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: ethanol / 6 h / 760.05 Torr / Reflux 2.1: hydrogen bromide; acetic acid / 2 h / 40 - 55 °C / 760.05 Torr 2.2: 760.05 Torr / Cooling with ice | ||
Multi-step reaction with 2 steps 1: ethanol / 6 h / Reflux 2: hydrogen bromide; acetic acid / 2 h / 55 °C | ||
Multi-step reaction with 2 steps 1: toluene; acetic anhydride / 18 h / 50 °C 2: acetic acid; hydrogen bromide / 18 h / 55 °C |
Multi-step reaction with 2 steps 1: ethanol / 15 h / 80 °C 2: acetic acid; hydrogen bromide / 15 h / 40 - 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene With hydrogen bromide; acetic acid at 40 - 55℃; for 2h; Stage #2: With sodium carbonate In water Cooling with ice; | ii.D General procedure: Dienoate (D-3) (148 mmol) is dissolved in AcOH (120 mL) and the mixture is stirred at 40 °C.A solution of 45% HBr-AcOH (120 mL) is added dropwise, and then the mixture is stirred at 55 °C for 2 h. The mixture is allowed to cool to RT, poured into ice -water, neutralized with solid Na2C03, and then extracted with ethyl acetate (3 x 150 mL). The combined organic layers are washed with brine (50 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on silica gel (5-20% ethyl acetate-petroether) to afford the product (D-4). | |
With hydrogen bromide; acetic acid at 55℃; for 2h; | 42 Method H; Example 42 Dienoate (H-3) (148 mmol) is dissolved in AcOH (120 mL) and the mixture is stirred at 40 °C. A solution of 45% HBr-AcOH (120 mL) is added dropwise, and then the mixture is stirred at 55 °C for 2 h. The mixture is allowed to cool to RT, poured into ice -water, neutralized with solid Na2C03, and then extracted with ethyl acetate (3 x 150 mL). The combined organic layer is washed with brine (50 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on silica gel (5- 20% ethyl acetate-petroether) to afford the product (H-4). | |
With hydrogen bromide; acetic acid at 55℃; for 18h; | 3 Step 3: Synthesis of Compound WX026-4 10379] WX026-3 (120.00 g, 576.20 mmol, 1.00 eq) was dissolved mAcOH (1.00 E), and H13r/AcOH (1.83 kg, 5.76 mol, 1.00 E, 35% purity, 10.00 eq) was added. The reaction liquid was stirred at 55° C. for 18 h. Afier reaction, the reaction liquid was dried by rotary evaporation, and the crude was purified by chromatographic column (petroleum ether:ethyl acetate=50:1-1:1) to obtain WX026-4. H NMR (400 MHz, CDC13) ö ppm: 8.25 (1H, d, J=5.27 Hz), 7.13 (1H, dd, J=5.02, 0.75 Hz), 4.45 (2H, q, J=7.03 Hz), 2.35 (3H, s), 1.42 (3H, t, J=7.15 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr 8.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr 8.2: 760.05 Torr 9.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 16 h / 20 °C / 760.05 Torr / Molecular sieve 10.1: tetrahydrofuran / -78 °C / 760.05 Torr / Inert atmosphere 10.2: 760.05 Torr 11.1: triphenylphosphine / tetrahydrofuran / 0.08 h / 0 °C / 760.05 Torr / Inert atmosphere 11.2: 2.33 h / 0 - 20 °C / 760.05 Torr / Inert atmosphere 12.1: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 20 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: ethyl 2-bromo-4-methylnicotinic acid With water; sodium hydroxide In 1,4-dioxane for 12h; Reflux; Stage #2: With hydrogenchloride In water | ii.D General procedure: To a solution of 4-substituted ethyl 2-bromolnicotinate (D-4) (52 mmol) in 1,4-dioxane (15 mL), a solution of NaOH (8.0 g, 200 mmol) in H20 (15 mL) is added and the resulting mixture is stirred at reflux for 12 h. The mixture is allowed to cool to RT, diluted with H20, and washed with ethyl acetate (3 x 30 mL). The aqueous layer is acidified with concentrated hydrochloric acid to adjust the pH to 1, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers are washed with brine (25 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo to afford the product nicotinic acid (D-5). | |
With water; sodium hydroxide In 1,4-dioxane for 12h; Reflux; | 42 Method H; Example 42 To a solution of 4 -substituted ethyl 2-bromolnicotinate (H-4) (52 mmol) in 1,4-dioxane (15 mL), a solution of NaOH (8.0 g, 200 mmol) in H20 (15 mL) is added and the resulting mixture is stirred at reflux for 12 h. The mixture is allowed to cool to RT, diluted with H20, and washed with ethyl acetate (3 x 30 mL). The aqueous layer is acidified with concentrated hydrochloric acid to adjust the pH to 1, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers are washed with brine (25 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo to afford the product nicotinic acid (H-5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr 8.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr 8.2: 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr 8.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr 8.2: 760.05 Torr 9.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 16 h / 20 °C / 760.05 Torr / Molecular sieve |
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