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CAS No. : | 947144-53-8 | MDL No. : | MFCD22574137 |
Formula : | C6H2ClF3N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 242.54 | Pubchem ID : | - |
Synonyms : |
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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#: | 2811 |
Hazard Statements: | H301-H311-H331 | Packing Group: | Ⅲ |
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 |
---|---|---|
73.4% | In tetrahydrofuran; at 20 - 50℃; for 18.5h; | 4-Chloro-3-nitro-6-trifluoromethyl-pyridin-2-ol (65.1 gm 268 mmol) was dissolved in tetrahydrofuran (350 ml_) and stirred at room temperature under N2. Benzylamine (86.3 gm 805 mmol) in tetrahydrofuran (50 ml.) was added drop wise over 30 minutes to give a bright yellow solution. The reaction was heated in an oil bath at 500C for 18 hours, (a solid formed during the reaction). Cooled to ambient temperature, diluted the reaction mixture with diethyl ether (200 ml_) and filtered off the solid (benzylamine hydrochloride). The filtrate was evaporated to low bulk under reduced pressure to give a thick yellow slurry. Added diethyl ether (300 ml.) and filtered off the yellow solid, dried on the filter pad to give the benzylamine salt (96.5 gm). The desired product was liberated by partition of the solid between aqueous 2N HCI and dichloromethane and crystallization from ethyl acetate/n-pentane gave 4-benzylamino- 3-nitro-6-trifluoromethyl-pyridin-2-ol as a pale yellow solid (61.7 gm 73.4% yield). |
73.4% | In tetrahydrofuran; at 20 - 50℃; for 18.5h; | PREPARATION 33; 4-Benzylamino-3-nitro-6-trifluoromethyl-pyridin-2-ol; 4-Chloro-3-nitro-6-trifluoromethyl-pyridin-2-ol (65.1 gm 268 mmol) was dissolved in tetrahydrofuran (350 mL) and stirred at room temperature under N2. Benzylamine (86.3 gm 805 mmol) in tetrahydrofuran (50 mL) was added drop wise over 30 minutes to give a bright yellow solution. The reaction was heated in an oil bath at 50 C. for 18 hours, (a solid formed during the reaction). The resulting mixture was then cooled to ambient temperature, diluted with diethyl ether (200 mL) and the resulting solid (benzylamine hydrochloride) was then filtered off. The filtrate was evaporated to low bulk under reduced pressure to give a thick yellow slurry. Added diethyl ether (300 mL) and filtered off the yellow solid, dried on the filter pad to give the benzylamine salt (96.5 gm). The desired product was liberated by partition of the solid between aqueous 2N HCl and dichloromethane and crystallization from ethyl acetate/n-pentane gave the title compound as a pale yellow solid (61.7 gm 73.4% yield).1H NMR (DMSO d6 9.04 (broad s, 1H), 7.38-7.25 (m, 5H), 6.54 (s,1H), 4.67 (d, 2H); LRMS (ES+) m/z 314 (MH+). |
Example 1; 5-amino-l-benzyl-7-(trifluoromethyl)pyridoi4 -b]pyrazine-2,3(lH,4 )-dione (5)Preparation of starting material 4-(benzylamino)-3-nitro-6-(trifluoromethyl)pyridin-2-ol (1)[000380] 4-Chloro-3-nitro-6-trifluoromethyl-pyridin-2-ol (1.8 g) was dissolved in tetrahydrofuran (10 mL) and stirred at room temperature under N2. Benzylamine (2.4 mL) was added drop wise to give a bright yellow solution. The reaction was heated in an oil bath at 50C for 18 hours and the resulting mixture was then cooled to ambient temperature, diluted with diethyl ether (10 mL) and the resulting solid (benzylamine hydrochloride) was then filtered off. The filtrate was evaporated under reduced pressure to give a thick yellow slurry. Diethyl ether (50 mL) was added and the yellow solid was filtered and dried to give the benzylamine salt. 4-(benzylamino)-3-nitro-6- (trifluoromethyl)pyridin-2-ol was obtained by partition of the solid between aqueous 2N HCI and dichloromethane. Crystallization from ethyl acetate/n-pentane gave 4-(benzylamino)-3-nitro-6- (trifluoromethyl)pyridin-2-ol as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[947144-26-5]3-Nitro-6-trifluoromethyl-pyridine-2,4-diol</strong> (5.8 gm, 26 mmol) was heated in phenylphosphonic dichloride (3OmL) at 1000C for 19 hours. Cooled and poured on to ice (60 gm), extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were washed with aqueous sodium hydrogen carbonate solution (10%w/v) until the washings remained basic (pH ~8). The deep yellow organic layer was then washed with saturated brine, dried over sodium sulphate, filtered and evaporated to give a yellow gum. Trituration of the gum with dichloromethane gave a yellow solid which was filtered off and dried (4.65gm). The solid was dissolved in water (25mL) and acidified with 2N hydrochloric acid (7.5mL) to give a thick white precipitate which was filtered off and washed with water. The precipitate was dissolved in ethyl acetate, dried over sodium sulphate, filtered and evaporated to give 4-chloro-3-nitro-6-trifluoromethyl- pyridin-2-as a white solid (3.75gm). | ||
PREPARATION 34; 4-Chloro-3-nitro-6-trifluoromethyl-pyridin-2-ol; <strong>[947144-26-5]3-Nitro-6-trifluoromethyl-pyridine-2,4-diol</strong> (5.8 gm, 26 mmol) was heated in phenylphosphonic dichloride (30 mL) at 100 C. for 19 hours. The resulting mixure was then cooled and poured on to ice (60 gm), and then extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with aqueous sodium hydrogen carbonate solution (10% w/v) until the washings remained basic (pH 8). The deep yellow organic layer was then washed with saturated brine, dried over sodium sulphate, filtered and evaporated to give a yellow gum. Trituration of the gum with dichloromethane gave a yellow solid which was filtered off and dried (4.65 gm). The solid was dissolved in water (25 mL) and acidified with 2N hydrochloric acid (7.5 mL) to give a thick white precipitate which was filtered off and washed with water. The precipitate was dissolved in ethyl acetate, dried over sodium sulphate, filtered and evaporated to give the title compound as a white solid (3.75 gm).1H NMR (DMSOd6) 7.78 (s, 1H). 13C NMR (DMSOd6) 157.2 (s) 145.2 (q) 138.1 (s) 136.98 (s) 120.6 (q) 113.86 (s). LRMS (ES-) m/z 241/243 [MH]- |