| Identification | More | [Name]
3-Amino-6-bromopyridine | [CAS]
13534-97-9 | [Synonyms]
2-AMINO-5-BROMOPYRIDINE
2-BROMO-5-AMINOPYRIDINE
3-AMINO-6-BROMOPYRIDINE
5-AMINO-2-BROMOPYRIDINE
5-BROMO-2-AMINOPYRIDINE
5-BROMOPYRIDIN-2-AMINE
5-BROMO-PYRIDIN-2-YLAMINE
6-BROMO-3-PYRIDINAMINE
6-BROMO-PYRIDIN-3-YLAMINE
AKOS BBS-00004444
LABOTEST-BB LT00129606
TIMTEC-BB SBB003823
TIMTEC-BB SBB005540
2-Bromo-5-aminoyridine
6-BROMOPYRIDIN-3-AMINE
6-Bromo-[3]pyridylamine
2-Bromo-5
5-Amino-2-bromopyridine 96% | [EINECS(EC#)]
214-019-9 | [Molecular Formula]
C5H5BrN2 | [MDL Number]
MFCD00006323 | [Molecular Weight]
173.01 | [MOL File]
13534-97-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow needles | [Melting point ]
75 °C | [Boiling point ]
180 °C | [density ]
1.6065 (rough estimate) | [refractive index ]
1.5182 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Powder | [pka]
1.87±0.10(Predicted) | [color ]
Beige to brown-black | [Detection Methods]
GC | [BRN ]
109102 | [InChI]
InChI=1S/C5H5BrN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2 | [InChIKey]
XTHKRYHULUJQHN-UHFFFAOYSA-N | [SMILES]
C1=NC(Br)=CC=C1N | [CAS DataBase Reference]
13534-97-9(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [PackingGroup ]
III | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow needles | [Uses]
3-Amino-6-bromopyridine may undergo polymerization via Buchwald–Hartwig amination in the presence of sodium tert-butoxide and XPhos(2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) ligand yielding para-linked and meta-linked polyaminopyridines. | [General Description]
3-Amino-6-bromopyridine can be synthesized via bromination of 3-aminopyridine using N-bromosuccinimide in acetonitrile. | [Synthesis]
General procedure for the synthesis of 5-amino-2-bromopyridine from 2-bromo-5-nitropyridine: To a solution of 2-bromo-5-nitropyridine (2.03 g, 10 mmol) in ethanol (48 mL) was added sequentially iron powder (2.8 g, 50 mmol), concentrated hydrochloric acid (1.9 mL) and water (9.1 mL). The reaction mixture was stirred under reflux conditions for 5 hours. After completion of the reaction, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure, the pH was adjusted to 7-8 with base and subsequently extracted with dichloromethane (DCM). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the reddish brown solid product 5-amino-2-bromopyridine (1.58 g, 91.3% yield). | [References]
[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Green Chemistry, 2018, vol. 20, # 1, p. 130 - 135
[3] Journal of Organic Chemistry, 2011, vol. 76, # 23, p. 9841 - 9844
[4] Patent: EP2886540, 2015, A1. Location in patent: Paragraph 0143; 0144
[5] Patent: US2014/93505, 2014, A1. Location in patent: Page/Page column |
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