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2-Bromo-5-amino-4-picoline

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2-Bromo-5-amino-4-picoline manufacturers
2-Bromo-5-amino-4-picoline Basic information
Product Name:2-Bromo-5-amino-4-picoline
Synonyms:5-Amino-2-bromo-4-methylpyridine;3-Pyridinamine, 6-bromo-4-methyl-;6-Bromo-4-methyl-3-pyridinamine;2-BROMO-5-AMINO-4-PICOLIN...;2-BROMO-5-AMINO-4-PICOLINE ISO 9001：2015 REACH;5-Amino-2-bromo-4-methylpyridine,98%;2-Bromo-5-amino-4-methylpyridine;6-BroMo-4-Methyl-pyridin-3-ylaMine
CAS:156118-16-0
MF:C6H7BrN2
MW:187.04
EINECS:
Product Categories:Heterocycle-Pyridine series;Amino-pyridine series;Pyridine;Boronic Acid
Mol File:156118-16-0.mol
2-Bromo-5-amino-4-picoline Structure
2-Bromo-5-amino-4-picoline Chemical Properties
Boiling point 306.9±37.0 °C(Predicted)
density 1.593±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
pka2.38±0.18(Predicted)
form Powder
color Brown
InChI1S/C6H7BrN2/c1-4-2-6(7)9-3-5(4)8/h2-3H,8H2,1H3
InChIKeyMVDBPMJQCXZKRB-UHFFFAOYSA-N
SMILESBrc1ncc(c(c1)C)N
CAS DataBase Reference156118-16-0
Safety Information
RIDADR UN2811
HazardClass 6.1
HS Code 2933399990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
2-Bromo-5-amino-4-picoline Usage And Synthesis
Synthesis
2-Bromo-5-nitro-4-picoline

23056-47-5

2-BROMO-5-AMINO-4-PICOLINE

156118-16-0

A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq.) was formed with NH4Cl (240 g, 4.49 mol, 4.87 eq.) in EtOH (3.50 L) and water (150 mL). The mixture was heated to 50 °C with stirring. Subsequently, Fe (120 g, 2.15 mol, 2.33 eq.) and HCl (10.2 g, 279 mmol, 0.30 eq.) were added to the mixture. The suspension was heated to 80 °C and kept for 3 hours. After completion of the reaction, the mixture was cooled to 25 °C and filtered through a diatomaceous earth plug. The filtrate was concentrated under reduced pressure to give a residue. The residue was dissolved in EtOAc (1L x 3) and washed with brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-4-methylpyridin-3-amine (XV) as a brown solid (167.9 g, 898 mmol, 97.4% yield), which could be used for the next reaction without further purification.1H NMR (CDCl3,400 MHz) δ ppm 2.15 (s, 3H), 3.44 (br s 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS m/z 186.8 ([M + H]+).

References[1] Patent: WO2017/23975, 2017, A1. Location in patent: Paragraph 0610; 0611
[2] Patent: WO2017/24026, 2017, A1. Location in patent: Paragraph 0614; 0615
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3441 - 3446
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5258 - 5264
[5] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 6, p. 2441 - 2452
2-Bromo-5-amino-4-picoline Preparation Products And Raw materials
Raw materials2-Bromo-5-nitro-4-picoline-->Ammonium chloride-->Hydrochloric acid-->Water-->Iron-->Ethanol
Tag:2-Bromo-5-amino-4-picoline(156118-16-0) Related Product Information
2-Bromo-5-amino-6- picoline 3-Amino-2-bromo-6-picoline 2-Bromo-5-amino-4-picoline 5-Amino-3-bromo-2-methylpyridine 4-Bromo-2-methyl-3-pyridinamine 2-BROMO-5-AMINO-3-PICOLINE 6-BROMO-3-AMINO-2-PICOLINE (5-AMINO-2-BROMO-6-PICOLINE),6-Bromo-5-amino-2-picoline 2-BROMO-3-AMINO-4-PICOLINE 2-BROMO-3-AMINO-5-PICOLINE 2-Bromo-5-Amino-6-Picoline 2-Bromo-5-Amino-6-Methyl Pyridine 4-Chlorophenethylamine 2-Bromo-5-nitro-4-picoline