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CAS No. : | 56-37-1 | MDL No. : | MFCD00011824 |
Formula : | C13H22ClN | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | HTZCNXWZYVXIMZ-UHFFFAOYSA-M |
M.W : | 227.77 | Pubchem ID : | 66133 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 trifluoroborane diethyl ether; In thionyl chloride; | Example 1 2-Chloromethyl-4-cyano-benzoyl chloride 1-Oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (25 g), boron trifluoride etherate (0.8ml), and benzyl triethyl ammonium chloride (0.72 g) were suspended in thionyl chloride (92 ml) and heated to reflux for 17 hours. Excess thionyl chloride was removed by distillation under nitrogen to give an internal temperature of 95° C., and heating to reflux was continued for another 24 hours. The product was purified by distillation under reduced pressure. Yield: 27.5 g, 92percent. Melting point 44 -44.5 C. 1H NMR (CDCl3, 400 MHz): 4.83 (2H, s), 7.74 (1H, dd, J=1, 8 Hz), 7.89 (1H, d, J=1 Hz), 8.25 (1H, d, J=8 Hz). 13C NMR (CDCl3, 100 MHz): 42.7, 116.8, 118.0, 132.2, 133.8, 134.0, 135.7, 140.0, 166.9. IR (KBr): v 3108, 3077, 2963, 2239, 1755, 1604, 1298, 1195, 1103, 944, 935, 840 cm-1. | |
With thionyl chloride; trifluoroborane diethyl ether; In 5,5-dimethyl-1,3-cyclohexadiene; | Example 2 2-Chloromethyl-4-cyano-benzoyl chloride 1-Oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (80 g), boron trifluoride etherate (4,4 ml), benzyltriethyl ammonium chloride (9,2 g), and thionyl chloride (55 ml) were suspended in xylene (320 ml). The mixture was heated to reflux for 4 hours and volatiles were removed under reduced pressure. The product was purified by distillation under high vacuum. Yield: 78,2 g, 73percent. Melting point 44 -44.5° C. 1H NMR (CDCl3, 400 MHz): 4.83 (2H, s), 7.74 1H, dd, J=1, 8 Hz), 7.89 1H, d, J=1 Hz), 8.25 1H, d, J=8 Hz). 13C NMR (CDCl3, 100 MHz): 42.7, 116.8, 118.0, 132.2, 133.8, 134.0, 135.7, 140.0, 166.9. IR (KBr): v 3108, 3077, 2963, 2239, 1755, 1604, 1298, 1195, 1103, 944, 935, 840 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; In acetonitrile; | Step A: 4-Chloro-2-hydroxy-3-nitropyridine Phosphorous oxychloride (63.4 mL, 0.68 mol) was added dropwise to a stirred mixture of 2,4-dihydroxy-3-nitropyridine (28.92 g, 0.17 mol) and benzyl triethylammonium chloride (155 g, 0.68 mol) in acetonitrile (560 mL). The reaction mixture was warmed to 60 C. for 1 h then was heated to reflux for 1 h. The reaction was cooled and the volatiles were evaporated in vacuo. An ice/water slurry (500 mL) was added to the residual oil and the mixture was stirred for 3 h at 0 C. The solids were collected by filtration, washing with water and hexanes to give the title compound as a solid; NMR (CD3 OD); d 2.33 (s, 3H), 6.39 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In chloroform; water; at 0 - 20℃; for 17h; | To a solution of <strong>[1075-35-0]5-chloro-2-methyl-1H-indole</strong> (5.00 g, 30.3 mmol) and TEBAC (0.60 g, 0.300 mmol) in CHCl3 (150 ml) was added, at 0 C., NaOH in water. The mixture was stirred at 0 C. for 3 h and then at RT for 14 h. The reaction mixture was then added gradually to ice-water and extracted with chloroform. The organic phase was washed with water, dried over Na2SO4 and concentrated on a rotary evaporator. The residue was purified by column chromatography purification with a hexane/ethyl acetate gradient as eluent. MH+: 212; 1H-NMR (400 MHz, CDCl3): δ 2.78 (s, 3H), 7.58-7.61 (dd, J=2.32 & 9.0 Hz, 1H), 7.68-7.69 (d, J=2.28 Hz, 1H), 7.91-7.94 (d, J=9.0 Hz, 1H), 8.01 (s, 1H). |