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2-Amino-5-bromopyridine

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2-Amino-5-bromopyridine Basic information
Product Name:2-Amino-5-bromopyridine
Synonyms:2-AMINO-5-BROMOPYRIDINE;AKOS BBS-00004444;5-BROMO-PYRIDIN-2-YLAMINE;5-BROMOPYRIDIN-2-AMINE;5-BROMO-2-AMINOPYRIDINE;5-bromo-2-pyridylamine;2-AMINO-5-BROMOPYRDIDINE;AMINO-5-BROMOPYRIDINE
CAS:1072-97-5
MF:C5H5BrN2
MW:173.01
EINECS:214-019-9
Product Categories:Amino-pyridine series;Bromopyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Organohalides;Aromatics;Heterocycles;Pyridines derivates;Organic acids;Pyridines, Pyrimidines, Purines and Pteredines;amine | alkyl bromide;FINE Chemical & INTERMEDIATES;Amines;blocks;Bromides;Pyridines;Pyridine;pyridine derivative;compounds of pyridine;bc0001
Mol File:1072-97-5.mol
2-Amino-5-bromopyridine Structure
2-Amino-5-bromopyridine Chemical Properties
Melting point 133-138 °C (lit.)
Boiling point 230.9±20.0 °C(Predicted)
density 1.6065 (rough estimate)
refractive index 1.5182 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka4.65±0.13(Predicted)
form Crystalline Powder
color White to beige
Water Solubility Soluble in methanol, chloroform, ethyl acetate. Slightly soluble in water.
BRN 108737
InChIInChI=1S/C5H5BrN2/c6-4-1-2-5(7)8-3-4/h1-3H,(H2,7,8)
InChIKeyWGOLHUGPTDEKCF-UHFFFAOYSA-N
SMILESC1(N)=NC=C(Br)C=C1
CAS DataBase Reference1072-97-5(CAS DataBase Reference)
EPA Substance Registry System2-Amino-5-bromopyridine (1072-97-5)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 26-36
RIDADR UN 2811 6.1/PG 3
WGK Germany 2
10
HazardClass IRRITANT
HS Code 29333999
MSDS Information
ProviderLanguage
2-Amino-5-bromopyridine English
ACROS English
SigmaAldrich English
ALFA English
2-Amino-5-bromopyridine Usage And Synthesis
Chemical PropertiesLight yellow Cryst
Uses2-Amino-5-bromopyridine is used for the synthesis of polycyclic azaarenes.
General Description2-Amino-5-bromopyridine is a brominated aromatic amine reagent and is used for labeling of model reducing-end oligosaccharides via reductive amination.
Synthesis
5-Bromo-2-nitropyridine

39856-50-3

2-Amino-5-bromopyridine

1072-97-5

General procedure for the synthesis of 2-amino-5-bromopyridine from 5-bromo-2-nitropyridine: 5-bromo-2-nitropyridine (0.6 mmol), 5 wt% Pd/C (0.5 mol%, 0.003 mmol), H2O (10 equiv, 6.0 mmol), B2(OH)4 (3.3 equiv, 2.0 mmol) and CH3CN ( 1.0 mL) were added to a 10 mL reaction tube. The reaction mixture was stirred at 50 °C for 24 hours. The progress of the reaction was monitored by TLC and when the reaction was complete, the mixture was cooled to room temperature. Water (5 mL) was added and extracted with EtOAc (3 x 5 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the target product 2-amino-5-bromopyridine (55 mg, 99% yield).

References[1] Tetrahedron, 2017, vol. 73, # 27-28, p. 3898 - 3904
[2] Organic Process Research and Development, 2017, vol. 21, # 2, p. 247 - 252
[3] Organic Letters, 2016, vol. 18, # 11, p. 2774 - 2776
[4] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[5] Yakugaku Zasshi, 1952, vol. 72, p. 381
Tag:2-Amino-5-bromopyridine(1072-97-5) Related Product Information
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