5-AMINO-3-BROMO-2-METHYLPYRIDINE
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5-AMINO-3-BROMO-2-METHYLPYRIDINE
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CAS No:
186593-43-1
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Formula:
C6H7BrN2
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Chemical Name:
5-AMINO-3-BROMO-2-METHYLPYRIDINE
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Synonyms:
5-AMINO-3-BROMO-2-METHYLPYRIDINE;3-Bromo-5-Amino-2-Picoline;5-Bromo-6-methylpyridin-3-amine;5-Amino-3-bromo-2-methylp...;2-Methyl-3-broMo-5-aMinopyridine;3-PyridinaMine, 5-broMo-2-chloro-6-Methyl-;5-BroMo-6-Methyl-pyridin-3-ylaMine;5-AMINO-3-BROMO-2-PICOLINE
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CAS No:
Characteristics
38.9
1.3
1.593±0.06 g/cm3(Predicted)
103.0 to 108.0 °C
281.3±35.0 °C(Predicted)
123.9±25.9 °C
1.617
0.00359mmHg at 25°C
Safety Information
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-AMINO-3-BROMO-2-METHYLPYRIDINE Use and Manufacturing
5-Bromo-6-methyl - pyridine-3-carboxylic acid (1 g, 4.63 mmol) wasdissolved in tert-butanol (6.6 mL) and N, N- dimethylformamide (15 mL), andthereto were added triethylamine (5.15 mL, 37.04mmol) and diphenylphosphorylazide (0.51 mL, 5.093 mmol). This mixture was heated to 100° Creaction 2h, after the end of the reaction by TLC, the solvent was evaporatedto dryness, and the residue was dissolved in saturated sodium bicarbonatesolution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and the solvent was evaporated to dryness, the residue on silica gelcolumn chromatography to give a white solid. The above white solid wasdissolved in dichloromethane (10 mL), was added 4N hydrogen chloride in dioxane, stirred for 2 hours at room temperature. After completion of the reaction, the solvent was evaporated to dryness to give 5-bromo-6-methyl -pyridin-3-ylamine (white solid, 130 mg).34d. 5-Acetoxy-3-bromo-2-methylpyridine The compound of Example 34c (12.6 g, 67 mmol) was treated with t-butyl nitrite and BF3.OEt2 followed by acetic anhydride according to the procedure of Example 1f. The crude product was chromatographed (silica gel; hexanes/EtOAc, 4:1) to afford the title compound (12.0 g, 58%): MS (CI/NH3) m/z: 230 (M+H)+.The title compound (Intermediate 48, 8.40 g, containing approximately 14% residual bis(pinacalato)diboron, 24.3 mmol) was prepared in three steps from 5-bromo-6- methylpyridin-3 -amine (Intermediate 47, 26.0 g, 139.0 mmol), sodium methanesulfinate (28.4 g, 278.2 mmol), copper iodide (26.5 g, 139.1 mmol), L-proline (16.0 g, 139.0 mmol) and NaOH (5.60 g, 140.0 mmol) in DMF (300 mL) at 110C for 18 h; fert-butyl nitrite (11.7 mL, 98.4 mmol) and CuBr2 (24.7 g, 110.6 mmol) in MeCN (180 mL) at 0C for 90 min; and [1, 1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1.24 g, 1.52 mmol), KOAc (8.95 g, 91.2 mmol) and bis(pinacolato)diboron (10.0 g, 39.4 mmol) in 1, 4-dioxane (38 mL) at 85C for 18 h, using the methods of Intermediate 46, steps 1 to 3.I2 (570 mg, 2.25 mmol) and Ag2S04 (733 mg, 2.35 mmol) were added to a mixture of
Computed Properties
Molecular Weight:187.04
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:185.97926
Monoisotopic Mass:185.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-AMINO-3-BROMO-2-METHYLPYRIDINE
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