| Identification | More | [Name]
3-Amino-5-bromopyridine | [CAS]
13535-01-8 | [Synonyms]
3-AMINO-5-BROMOPYRIDINE
5-BROMO-3-AMINOPYRIDINE
5-BROMO-3-PYRIDINAMINE
5-BROMO-PYRIDIN-3-YLAMINE
CHEMBRDG-BB 4006048
5-BROMOPYRIDIN-3-AMINE
3-amino-5-bronopyridine
3-AMINO-5-BOROMOPYRIDINE
13535-01-8 | [EINECS(EC#)]
629-312-0 | [Molecular Formula]
C5H5BrN2 | [MDL Number]
MFCD01646060 | [Molecular Weight]
173.01 | [MOL File]
13535-01-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Cryst | [Melting point ]
65-69 °C
| [Boiling point ]
149-150 °C(Press: 12 Torr) | [density ]
1.710±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Powder | [pka]
3.81±0.20(Predicted) | [color ]
White to yellow to brown | [InChI]
InChI=1S/C5H5BrN2/c6-4-1-5(7)3-8-2-4/h1-3H,7H2 | [InChIKey]
MDQXGHBCDCOOSM-UHFFFAOYSA-N | [SMILES]
C1=NC=C(Br)C=C1N | [CAS DataBase Reference]
13535-01-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi,O | [Risk Statements ]
R22:Harmful if swallowed.
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 .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
Cool, dry,tightly closed | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow Cryst | [Uses]
3-Amino-5-bromopyridine is used in green preparation of tryptamine salicylic acid compounds as antitumor agent. | [Synthesis]
General procedure for the synthesis of 5-bromo-3-aminopyridine from 5-bromonicotinamide:
1. To a pre-cooled 340 ml aqueous solution containing 31.8 g (0.79 mol) of sodium hydroxide and 40.7 g (0.255 mol) of bromine, 42.0 g (0.209 mol) of commercially available 5-bromonicotinamide was added.
2. The reaction mixture was gradually warmed to room temperature, followed by heating the reaction at 70 °C for 1 hour.
3. Upon completion of the reaction, the resulting brown suspension was allowed to cool to room temperature.
4. The aqueous phase was treated with saturated brine and then extracted three times with a 1:1 solvent mixture of THF and tert-butyl methyl ether.
5. The organic phases were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure.
6. 39.1 g of the dark brown residue obtained from the concentration was purified by fast chromatography (eluent: heptane/ethyl acetate 1:1) to yield 5-bromo-3-aminopyridine as a brown solid (total yield 70.2 g, 70% yield). | [References]
[1] ChemMedChem, 2014, vol. 9, # 1, p. 217 - 232
[2] Patent: US2006/160857, 2006, A1. Location in patent: Page/Page column 56
[3] Patent: US2006/199960, 2006, A1. Location in patent: Page/Page column 21
[4] Patent: US2006/217387, 2006, A1. Location in patent: Page/Page column 31
[5] Patent: US2003/199511, 2003, A1. Location in patent: Page/Page column 23 |
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