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CAS No. : | 38835-18-6 | MDL No. : | MFCD03421603 |
Formula : | C14H13ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 248.70 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 | UN#: | 1759 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
With thionyl chloride; In chloroform; | c) 7 ml of thionyl chloride were cautiously added to a solution of 2.3 g of 2-(6-methoxy-2-naphtyl)propionic acid in 15 ml of anhydrous chloroform. The reaction mixture was stirred for 40 minutes at room temperature and then the solvent was evaporated at a reduced pressure, obtaining 2.23 g of 2-(6-methoxy-2-naphtyl)propionylchloride. | |
With thionyl chloride; for 4h;Heating / reflux; | A solution of commercially available racemic <strong>[23981-80-8]naproxen</strong> (0.92g, 4.0 mmol) in thionyl chloride [(5ML)] was refluxed until the evolution of the [HCL] gas had ceased (ca. 4 h). The excess thionyl chloride was removed in vacuo and a 1: 1 mixture of ethanol (3mL): [DICHLOROMETHANE] (3mL) was added with refluxing for further 2h. The solution was cooled and the solvent removed in vacuo to give <strong>[23981-80-8]naproxen</strong> ethyl ester as a colourless oil (1.03g, 80%) after purification via flash chromatography (96: 4) ) (hexane: ethyl acetate). | |
With thionyl chloride; In benzene;Reflux; | General procedure: A solution of NSAIDs having carboxylic acid group (1a-h) (1 mmol) in dry benzene (5-8 mL) was refluxed with freshly distilled thionyl chloride (1.2 mmol) for 2-3 h. After the completion of reaction, excess of thionyl chloride was removed under reduce pressure to afford the acid chlorides (2a-h) which were dissolved in anhydrous acetone for further use. The acid chlorides (2a-h) were then treated with a solution of (+)-6-aminopenicillanic acid (6-APA, 1 mmol) in 2% NaHCO3 (40 mL) diluted with acetone (30 mL). The reaction mixture was stirred for 2-4 h at room temperature and then concentrated under reduced pressure and washed with ethyl acetate (25 mL). The aqueous layer was then acidified with HCl (0.1 M), extracted with ethyl acetate and then washed with distilled water dried over anhydrous Na2SO4. The ethyl acetate was rotary evaporated and triturated with n-hexane to afford the title compounds (4a-h). |
With thionyl chloride; In N,N-dimethyl-formamide; at 25 - 75℃;Inert atmosphere; | General procedure: A solution of the carboxylic acid drug (3) (0.031 mol) and DMF in dry SOCl2 (3-10 mL) was heated at 25-75 C for 2-5 h under a nitrogen atmosphere. Then the reaction mixture was concentrated by evaporation. The residue was added to a solution of (2) (0.012 mol) in 40 mL acetonitrile and stirred for 2-4 h at room temperature, while monitoring the reaction by TLC. Finally, the reaction product was concentrated in vacuo and purified by silica gel with CH2Cl2/CH3OH (70:1-10:1) as eluent to obtain the proposed compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7 EXAMPLE 7 EXAMPLE 7 N-[2-(6-Methoxy-2-naphthyl)-2-methylethyl]-N-[3-(diisobutylamino)-1-propyl]amine, prepared by reaction of d,l-α-(6-methoxy-2-naphthyl)propionyl chloride with N,N-diisobutyl-1,3-propanediamine and reduction of the resulting N-[α-(6-methoxy-2-naphthyl)propionyl]-N-[3-(diisobutylamino)-1-propyl]amine with lithium aluminum hydride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With pyridine; In dichloromethane; at 20℃; | Example 12 - DPX-2-0001 (ALE 406) 4-( dimethylamino)phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate. 2-(6-methoxynaphthalen-2-yl)propanoyl chloride (acid chloride of Naproxen) (1 g, 4 mmol) was dissolved in dichloromethane (20 mL) and pyridine (30 mL) was added, and finally a solution of the 2-(4-(dimethylamino)phenyl) ethanol (0.64 g, 4 mmol) in dichloromethane (10 mL) was added. The mixture was left over night under stirring at room temperature. After addition of dichloromethane the reaction mixture was washed with first a saturated bicarbonate solution (100 mL) and second water (100 mL). The organic phase was dried and concentrated to yield an oily residue. The crude product was purified by vacuum liquid chromatography on silica (20-45 pm) using heptane (60 mL) followed by heptane-ethyl acetate (4:1 v/v) as eluent. Yield 0.52 g (35 %). 1H R (300MHz, CDCI3): delta 7.70-7.64 (3H, m); 7.37 (1 H, dd, J=6.60; 1.5 Hz); 7.15 - 7.1 1 (2H, m); 6.9 (2H, d, J=8.8 Hz); 6,52 (2H, d, J=8,56); 4,27(2H, t, J=6,88 Hz); 3,92 (3H,s); 3.84 (1 H, q, J=7.15 Hz); 2.88 (6H, s); 2.76 (2H, t, J=7.15 Hz); 1.57 (3H, d, J=7.15 Hz). 13C NMR (400 MHz, DMSO-d6) delta 173.76, 157.18, 135.60, 135.60, 129.24, 126.96, 126.23, 125.73, 1 18.66, 105.69, 65.29, 55.15, 44.51 , 33.30, 18.17. |
35% | With pyridine; In dichloromethane; at 20℃; | 4-(dimethylamino)phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate 2-(6-methoxynaphthalen-2-yl)propanoyl chloride (acid chloride of Naproxen) (1 g, 4 mmol) was dissolved in dichloromethane (20 mL) and pyridine (30 mL) was added, and finally a solution of the 2-(4-(dimethylamino)phenyl) ethanol (0.64 g, 4 mmol) in dichloromethane (10 mL) was added. The mixture was left over night under stirring at room temperature. After addition of dichloromethane the reaction mixture was washed with first a saturated bicarbonate solution (100 mL) and second water (100 mL). The organic phase was dried and concentrated to yield an oily residue. The crude product was purified by vacuum liquid chromatography on silica (20-45 mum) using heptane (60 mL) followed by heptane-ethyl acetate (4:1 v/v) as eluent. Yield 0.52 g (35%). 1H NMR (300 MHz, CDCl3): delta 7.70-7.64 (3H, m); 7.37 (1H, dd, J=6.60; 1.5 Hz); 7.15-7.11 (2H, m); 6.9 (2H, d, J=8.8 Hz); 6.52 (2H, d, J=8.56); 4.27 (2H, t, J=6, 88 Hz); 3.92 (3H, s); 3.84 (1H, q, J=7.15 Hz); 2.88 (6H, s); 2.76 (2H, t, J=7.15 Hz); 1.57 (3H, d, J=7.15 Hz). 13C NMR (400 MHz, DMSO-d6) delta 173.76, 157.18, 135.60, 135.60, 129.24, 126.96, 126.23, 125.73, 118.66, 105.69, 65.29, 55.15, 44.51, 33.30, 18.17. |
35% | With pyridine; In dichloromethane; at 20℃; | 2-(6-methoxynaphthalen-2-yl)propanoyl chloride (acid chloride of Naproxen) (1 g, 4 mmol) was dissolved in dichloromethane (20 mL) and pyridine (30 mL) was added, and finally a solution of the 2-(4-(dimethylamino)phenyl) ethanol (0.64 g, 4 mmol) in dichloromethane (10 mL) was added. The mixture was left over night under stirring at room temperature. After addition of dichloromethane the reaction mixture was washed with first a saturated bicarbonate solution (100 mL) and second water (100 mL). The organic phase was dried and concentrated to yield an oily residue. The crude product was purified by vacuum liquid chromatography on silica (20-45 muetaeta) using heptane (60 mL) followed by heptane-ethyl acetate (4:1 v/v) as eluent. Yield 0.52 g (35%). 1H NMR (300MHz, CDCI3): delta 7.70-7.64 (3H, m); 7.37 (1H, dd, J=6.60; 1.5 Hz); 7.15 - 7.11 (2H, m); 6.9 (2H, d, J=8.8 Hz); 6,52 (2H, d, J=8,56); 4,27(2H, t, J=6,88 Hz); 3,92 (3H,s); 3.84 (1H, q, J=7.15 Hz); 2.88 (6H, s); 2.76 (2H, t, J=7.15 Hz); 1.57 (3H, d, J=7.15 Hz). 13C NMR (400 MHz, DMSO-d6) delta 173.76, 157.18, 135.60, 135.60, 129.24, 126.96, 126.23, 125.73, 118.66, 105.69, 65.29, 55.15, 44.51, 33.30, 18.17. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With pyridine In 1,4-dioxane for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With pyridine In 1,4-dioxane for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.9% | diethylaminoethanol 11.7 g (0.1 mol) was dissolved in 10% sodium bicarbonate (200ml) and acetone (100ml). 2-(6-methoxy-2-naphthyl)propionyl chloride 24.9g (0.1mol) was added to the reaction mixture. The mixture is stirred for 3 hours at room temperature. The solvent is evaporated. The residue is suspended in ethyl acetate (500ml). 5% sodium bicarbonate (200ml) is added to the reaction mixture while stirring. The ethyl acetate layer was collected, washed with water (3 × 500ml). The resulting ethyl acetate solution was dried over anhydrous sodium sulfate. the sodium sulfate was removed by filtration. With stirring, acetic acid 6g was added to the reaction mixture. The organic solution was evaporated. After drying, the desired product 36g (89.9%) was obtained. | |
89.9% | 11.7 g (0.1 mol) of diethylaminoethanol was dissolved in 10% sodium bicarbonate (200 ml) and acetone (100 ml).24.9 g (0.1 mol) of 2- (6-methoxy-2-naphthyl) propionyl chloride was added to the reaction mixture.The residue is suspended in ethyl acetate (500 ml). 5% sodium bicarbonate (200 ml) is added to the reaction mixture with stirring. The ethyl acetate layer is collected and washed with water (3 × 500 ml). The resulting ethyl acetate solution was dried over anhydrous sodium sulfate. The sodium sulfate is removed by filtration. 6 g of acetic acid are added to the reaction mixture with stirring. The organic solution was evaporated. After drying, 36 g (89.9%) of the desired product was obtained. Hygroscopic product, solubility in water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In dichloromethane at 20℃; Inert atmosphere; |