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CAS No. : | 5912-35-6 | MDL No. : | MFCD09702034 |
Formula : | C8H6BrN3 | Boiling Point : | 407.187°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 224.06 | Pubchem ID : | 10704335 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | 51.8 | H-Bond Acceptor Count : | 3 |
XLogP3 : | 1.8 | H-Bond Donor Count : | 1 |
SP3 : | 0.00 | Rotatable Bond Count : | 0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: at 0℃; for 0.50 h; Stage #2: With sodium hydrogencarbonate In water |
(3) 8-bromo-l,7-naphthyridin-6-amine.; To a 50 mL round-bottomed flask was added hydrobromic acid, 30percent in acetic acid (317 μl, 5868 μmol). 3-(cyanomethyl)picolinonitrile (280 mg, 1956 μmol) in AcOH (0.5 mL) was then added at 0 0C. The reaction mixture was stirred at 0 0C for 30 min. The solid was filtered out and washed with 50percent EtOAc/hexanes. The solid was treated with sat. NaHCO3 (5 mL) and the mixture was extracted with EtOAc (2 x 50 mL). The organic extract was washed with satd NaCl (5 mL), dried over Na2SO4, filtered and <n="130"/>concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 40percent EtOAc/hexanes to give 8-bromo-l,7-naphthyridin-6-amine (312 mg, 71percent yield). MS (ESI pos. ion) m/z calc'd for C8H6BrN3: 223.0, 225.0; found 224.0, 226.0. 1H NMR (300 MHz, CHLOROFORM-^) δ ppm 4.63 (s, 2 H) 6.61 (s, 1 H) 7.42 (dd, J=8.48, 4.09 Hz, 1 H) 7.85 (dd, J=8.48, 1.61 Hz, 1 H) 8.78 (dd, J=3.95, 1.61 Hz, 1 H) |
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