| Identification | More | [Name]
4-Amino-3-bromopyridine | [CAS]
13534-98-0 | [Synonyms]
1H-PYRAZOLE-5-CARBOXYLIC ACID
2H-PYRAZOLE-3-CARBOXYLIC ACID
AKOS BBS-00005959
AKOS PAO-0460
IFLAB-BB F3250-0675
4-AMINO-3-BROMOPYRIDINE
3-Bromo-4-aminopyridine
3-Bromo-4-pyridinamine
3-Bromo-4-aminopyridine, 3-Bromo-4-pyridinamine | [EINECS(EC#)]
628-420-5 | [Molecular Formula]
C5H5BrN2 | [MDL Number]
MFCD00464252 | [Molecular Weight]
173.01 | [MOL File]
13534-98-0.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow Cryst | [Melting point ]
61-69 °C | [Boiling point ]
275.8±20.0 °C(Predicted) | [density ]
1.6065 (rough estimate) | [refractive index ]
1.5182 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Powder | [pka]
pK1: 7.04(+1) (20°C) | [color ]
White to off-white | [BRN ]
110183 | [InChI]
InChI=1S/C5H5BrN2/c6-4-3-8-2-1-5(4)7/h1-3H,(H2,7,8) | [InChIKey]
DDQYSZWFFXOXER-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(N)=C1Br | [CAS DataBase Reference]
13534-98-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT, AIR SENSITIVE | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow Cryst | [Synthesis]
General procedure for the synthesis of 4-amino-3-bromopyridine from 4-aminopyridine: To a mixture of 4-aminopyridine (20.0 g, 0.21 mol) and acetonitrile (300.0 mL) was added N-bromosuccinimide (NBS) (39.8 g, 0.22 mol) in batches at 0 °C, the reaction was to be carried out protected from light. Subsequently, the reaction mixture was stirred at room temperature for 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by fast column chromatography (silica gel as stationary phase and dichloromethane/methanol=20:1 as eluent) to afford the target compound 4-amino-3-bromopyridine (33.2 g, 91.4% yield) as a light yellow solid. Mass spectrum (ESI) m/z: 172.9 [M + H]+. | [References]
[1] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 37 - 50
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 15, p. 3216 - 3231
[3] Patent: US2003/22883, 2003, A1
[4] Journal of the American Chemical Society, 2012, vol. 134, # 31, p. 12928 - 12931 |
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