6-Amino-5-bromo-3-pyridinecarbonitrile
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6-Amino-5-bromo-3-pyridinecarbonitrile
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CAS No:
477871-32-2
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Formula:
C6H4BrN3
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Chemical Name:
6-Amino-5-bromo-3-pyridinecarbonitrile
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Synonyms:
3-Pyridinecarbonitrile,6-amino-5-bromo-;6-Amino-5-bromo-3-pyridinecarbonitrile;6-Amino-5-bromonicotinonitrile;6-Amino-5-bromopyridine-3-carbonitrile
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CAS No:
Safety Information
IRRITANT
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
6-Amino-5-bromo-3-pyridinecarbonitrile Use and Manufacturing
8- [ (3-Methyl-butylamino)-methyl]-10, 11-dihydro-5-oxa-4-aza- dibenzo [a, d] cycloheptene-2-carboxylic acid amide; Step 1; 6-Amino-5-bromo-nicotinonitrile; To a solution of 6-Amino-nicotinonitrile (102 mg, 0.86 mmol) in AcOH (2 mL) add a solution of Br2 l. OM in AcOH (0.86 mmol). Stir the mixture at room temperature for 2 hours. Eliminate the solvent. Purify by flash chromatography on silica gel (eluent: hexane/EtOAc 3/1) to afford the title compound (110 mg, 65percent). 'H-NMR (DMSO, 300 MHz): 8.26 (d, 1 H, J= 2.0 Hz), 8.10 (d, 1H, J= 2.0 Hz), 7.24 (bs 2H). MS (APCI Neg) : 196, 198To a well stirred solution of 6-aminopyridine-3-carbonitrile (8.0 g, 67.15 mmol) in tetrahydrofuran (100 ml) was added N-bromosuccinimide (17.92 g, 100.72 mmol) and stirred at room temperature for 1 h. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (2 x 200 ml). The combined organic layers were washed with 2N sodium hydroxide solution (100 ml) and brine (100 ml). The mixture was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue obtained was crystallized from a mixture of diethyl ether and n-pentane to yield 11.2 g of product as a white solid.To a solution of 6-aminonicotinonitrile (5.0 g) in acetic acid (50 mL) was added bromine (4.3 mL) under ice-cooling. Reference Example 341
Computed Properties
Molecular Weight:198.02
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:62.7
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-Amino-5-bromo-3-pyridinecarbonitrile
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