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CAS No. : | 344-19-4 | MDL No. : | MFCD00142845 |
Formula : | C6H4Cl2FN | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | YAUYKCFMKMZTEX-UHFFFAOYSA-N |
M.W : | 180.01 | Pubchem ID : | 2774008 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 | UN#: | 2811 |
Hazard Statements: | H301+H311+H331-H315-H319 | 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 |
---|---|---|
96% | Preparation 10 2,6 Dichloro-4-fluoro-phenylhydrazine hydrochlorideTo a 0 0C solution of 2,6 Dichloro-4-fluorophenylamine (3.0 g, 16.6 mmol) in 12 M HCl (30 mL) and TFA (20 mL) is added slowly and dropwise NaNO2 (20 mmol, 1.37 mL) in water (6 mL). The reaction is stirred at 0 0C for 1 h. A solution of SnCl2 (5.74 g, 25.6 mmol) in 12 M HCl (16 mL) is added over 15 minutes. The ice bath is removed and <n="24"/>the reaction is stirred for 18 h. The reaction is filtered and the solid is washed with isopropyl alcohol. The solid is dried to yield the title compound (3.0 g, 96 %). LC-ES/MS m/e 194.0 (M+ 1) | |
Step 1: (2,6-dichloro-4-fluorophenyl)hydrazine hydrochloride To a - 5 C solution (internal temperature, wet ice/acetone bath) of <strong>[344-19-4]2,6-dichloro-4-fluoroaniline</strong> (3.0 g, 17 mmol) in 37 % hydrochloric acid (30 mL) and trifluoroacetic acid (20 mL) was added dropwise an aqueous solution of sodium nitrite (1.4 g, 20 mmol, 6 mL water). The reaction was stirred for 90 minutes, then a solution of stannous chloride dihydrate (5.6 g, 25 mmol) in 37 % hydrochloric acid (16 mL) was added over 15 minutes, keeping the internal temperature ? 2 C. The mixture was stirred overnight at room temperature. The mixture was filtered and the collected solid was washed with isopropyl alcohol and dried under house vacuum to provide the title compound. LCMS-ESI+ (m/z): [M+H]+ calcd for C6H6Cl2FN2: 195.0; found: 194.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | PREPARATION CXXXVI; 2,6-dichloro-4-fluorobenzenesulphonyl chloride; A solution of 4.75 g (25 mM) of <strong>[344-19-4]2,6-dichloro-4-fluoroaniline</strong> in 50 ml of dichloromethane are added, at -15 C., to 4.75 ml of boron trifluoride etherate. 5 ml of tetrahydrofuran are added to dissolve the precipitate formed, then, slowly, 3.6 ml of t-butyl nitrite in solution in 25 ml of dichloromethane are added. The reaction mixture is agitated 10 minutes at -15 C. and then 20 minutes at +5 C. 200 ml of pentane are added, and agitation is maintained at 0 C. for 30 min and the precipitate is filtered off. After drying, 7.2 g of the diazonium salt are obtained. This salt is dissolved in 30 ml of acetonitrile and is added, at 10 C., to a mixture of a solution of sulphur dioxide in 90 ml of acetic acid to which 1.4 g of anhydrous copper (II) chloride and 23 ml of concentrated hydrochloric acid have been added. The reaction mixture is agitated 30 min at ambient temperature and then concentrated under reduced pressure. The residue from evaporation is taken up into 60 ml of dichloromethane and the insoluble salts are removed by filtration. The filtrate is concentrated under reduced pressure to give 4.71 g of the product sought after as orange crystals (yield=71%). M.Pt.=57 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sodium nitrite; In hydrogenchloride; water; | PREPARATION OF 2,6-DICHLORO-4-FLUOROPHENYLHYDRAZINE (INTERMEDIATE NO. 2) 9.0 g (0.05 mol) of <strong>[344-19-4]2,6-dichloro-4-fluoroaniline</strong> was added to 50 ml of concentrated hydrochloric acid, and a solution of 3.8 g (0.055 mol) of sodium nitrite in 25 ml of water was dropwise added thereto at a temperature of from 0 to 5 C. After completion of the dropwise addition, the mixture was stirred at the same temperature for further 1 hour. Insolubles were removed by filtration, and the filtrate was dropwise added at a temperature of from 0 to 10 C. to a solution of 33.8 g (0.15 mol) of stannous chloride dihydrate in 50 ml of concentrated hydrochloric acid. After completion of the dropwise addition, the mixture was stirred at the same temperature for further 2 hours. The precipitated hydrochloride was collected by filtration, and 50 ml of water was added thereto. The mixture was made alkaline with an addition of 20% sodium hydroxide, and the precipitated solid was extracted with ethyl ether. The ethyl ether layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The residue thereby obtained was washed with cold n-hexane to obtain 6.9 g (yield: 70.4%) of the desired compound as white feather-like crystals. Melting point: 117-119 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium tetrachloride; triethylamine; In dichloromethane; at 0 - 20℃; for 5h; | Method 2:Example 43 :2-(2,6-Dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)- amineStep 1 : [l-(4-Azido-5-fluoropyridin-3-yl)-meth-(£)-ylidene]-(2,6-dichloro-4-fluorophenyl)-amineTo a cooled (0 C) solution of 4-azido-5-fluoro-pyridine-3-carbaldehyde (2.44 g, 14.7 mmol), 2,6-dichloro-4- fluorophenylamine (2.65 g, 14.7 mmol) and triethylamine (6.1 mL, 44 mmol) in DCM (50 mL) was added titanium tetrachloride (1M in DCM, 8.8 mL, 8.8 mmol) dropwise. The reaction mixture was stirred at 0 C for 1 hour, warmed to room temperature, and stirred for a further 4 hours. The mixture was concentrated under reduced pressure. The residue was dissolved in toluene and filtered through Celite. The filtrate was concentrated under to dryness under reduced pressure to afford the title compound that was used without further purification. |