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type | HazMat fee |
Excepted Quantity | Free |
Inaccessible (Haz class 6.1), Domestic | USD 41.00 |
Inaccessible (Haz class 6.1), International | USD 64.00 |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 83.00 |
Accessible (Haz class 3, 4, 5 or 8), International | USD 133.00 |
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CAS No. : | 372198-49-7 | MDL No. : | MFCD09741164 |
Formula : | C8H6ClNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 215.66 | Pubchem ID : | 16794335 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | - | H-Bond Acceptor Count : | - |
XLogP3 : | - | H-Bond Donor Count : | - |
SP3 : | - | Rotatable Bond Count : | - |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | 3-Amino-4-methylbenzonitrile (407 mg, 3.09 mmol) was suspended in concentrated HCl (3 mL) at 0 C. A solution of NaNO2 (320 mg, 4.64 mmol) in water (1 mL) was added dropwise over 5 min, and the solution stirred for 45 min. Meanwhile, AcOH (3 mL) was saturated with SO2, then CuCl2·2H2O (158 mg, 0.93 mmol) was added and SO2 bubbled through for a further 5 min. The AcOH mixture was cooled to 5 C, then the diazonium solution added over 5 min. The resulting mixture was stirred for a further 1.5 h, then the precipitate filtered off, washed with a little water and dried to leave 5-cyano-2-methylbenzenesulfonyl chloride as a yellow solid (167 mg, 25%). 1H NMR delta (400 MHz, CDCl3) 8.36 (d, J = 1.7 Hz, 1H), 7.87 (dd, J = 7.9, 1.7 Hz, 1H), 7.58 (d, J = 7.9 Hz, 1H), 2.88 (s, 3H). LC-MS (APCI-) 196 (M-Cl+O, 100%). Reaction of 2 (30 mg, 0.18 mmol) and the above sulfonyl chloride (45 mg, 0.21 mmol) using NaHCO3, after chromatography (eluting with CH2Cl2:MeOH 99.75:0.25) gave 6j as a yellow solid (32 mg, 48%). | |
25% | Step 21.1 : 3-Amino-4-methylbe?zonitrile (52: X = Me1 Y = CN) (407 mg, 3.09 mmol) was suspended in concentrated HCI (3 mL) at 0 0C. A solution of NaNO2 (320 mg, 4.64 mmol) in water (1 mL) was added dropwise over 5 mins, and the solution stirred for 45 mins. Meanwhile, AcOH (3 mL) was saturated with SO2, then CuCI2.2H2O (158 mg, 0.93 mmol) was added and SO2 bubbled through for a further 5 mins. The AcOH mixture was cooled to 5 0C, then the diazonium solution added over 5 mins. The resulting mixture was stirred for a further 1.5h, then the precipitate filtered off, washed with a little water and dried to leave 5-cyano-2-methylbenzenesulfonyl chloride (53: X = Me, Y = CN) as a yellow solid (167 mg, 25%). 1H NMR delta (400 MHz, CDCI3) 8.36 (d, J 1.7 Hz, 1 H), 7.87 (dd, J 7.9, 1.7 Hz, 1 H), 7.58 (d, J 7.9 Hz, 1 H), 2.88 (s, 3H). LCMS (APCI ) 196 (M-CI+O, 100%). | |
A solution of 3-amino-4-methyl-benzonitrile (454mg) in cone. HCl (3.5mL) and AcOH (4mL) was cooled to -10C. To this was added a solution OfNaNO2 (284mg) in water (2.1ml) dropwise. After stirring for 15 minutes the mixture was added to a cooled (5C) solution of CuCl (85mg) in AcOH (7mL) that had previously been saturated with SO2 gas. The reaction mixture was warmed to room temperature, SO2 was removed in vacuo and then water was added to yield the title compound as a white solid which was collected by filtration. (520mg). |
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