| Identification | More | [Name]
3,5-Dibromo-2-pyridylamine | [CAS]
35486-42-1 | [Synonyms]
2-AMINO-3,5-DIBROMOPYRIDINE
2-PYRIDINAMINE, 3,5-DIBROMO-
3,5-DIBROMOPYRIDIN-2-AMINE
AKOS BB-8249
AKOS BBS-00001351
ASISCHEM X26831
AURORA KA-520
LABOTEST-BB LT00000217
SALOR-INT L495980-1EA
TIMTEC-BB SBB000910
2-amino-3,5-dibromopyridinehydrate
3,5-dibromo-2-pyridylamine
3,5-Dibromo-pyridin-2-ylamine
2-Amino-3,5-dibromo
2-Amino-3,5-dibromopyridine
2-Amino-3,5-dibromo pyridine ,99%
3,5-Dibromo-2-pyridinamine | [EINECS(EC#)]
252-590-6 | [Molecular Formula]
C5H4Br2N2 | [MDL Number]
MFCD00038041 | [Molecular Weight]
251.91 | [MOL File]
35486-42-1.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to brown fine crystalline powder | [Melting point ]
104-105 °C (lit.) | [Boiling point ]
253.9±35.0 °C(Predicted) | [density ]
2.147±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
1.89±0.49(Predicted) | [Detection Methods]
HPLC | [BRN ]
119390 | [InChI]
InChI=1S/C5H4Br2N2/c6-3-1-4(7)5(8)9-2-3/h1-2H,(H2,8,9) | [InChIKey]
WJMJWMSWJSACSN-UHFFFAOYSA-N | [SMILES]
C1(N)=NC=C(Br)C=C1Br | [CAS DataBase Reference]
35486-42-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
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 .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow to brown fine crystalline powder | [General Description]
The synthesis of 2-amino-3,5-dibromopyridine complexes and their analysis by single crystal X-ray diffraction has been studied. | [Synthesis]
General procedure for the synthesis of 2-amino-5-bromopyridine and 2-amino-3,5-dibromopyridine from 2-aminopyridine: 28.2 g (0.3 mol) of 2-aminopyridine was dissolved in 50 ml of acetic acid. The solution is cooled to below 20°C by means of an ice bath and 48 g (15.4 ml, 0.3 mol) of bromine dissolved in 30 ml of acetic acid is added slowly and dropwise over a period of 1 h under vigorous stirring. The temperature was maintained below 20°C at the beginning of the reaction. Upon addition of half of the bromine solution, the reaction temperature was raised to 50°C to promote precipitation of 2-amino-5-bromopyridine hydrobromide. At 50°C, the hydrobromide typically begins to crystallize when about three-quarters of the bromine is added. After completion of the bromine addition, stirring of the reaction mixture was continued for 1 hour, followed by dilution with 75 mL of water to dissolve the hydrobromide. The reaction solution is transferred to a 500 ml beaker and neutralized by the slow addition of 120 ml of 40% sodium hydroxide solution under stirring and cooling conditions. Filtration and drying gave a crude product of 2-amino-5-bromopyridine containing a small amount of 2-amino-3,5-dibromopyridine. The 2-amino-3,5-dibromopyridine was removed from the crude product by washing with 500 ml of hot petroleum ether in three passes. The final yield of 2-amino-5-bromopyridine was 32-34.7 g (62-67% yield) with a melting point of 134°C (literature value: 132-135°C). | [Purification Methods]
Steam distil it and recrystallise it from aqueous EtOH or pet ether. [Beilstein 22 H 431, 22 II 333, 22 III/IV 4041.] | [References]
[1] Synthetic Communications, 1986, vol. 16, # 13, p. 1641 - 1646
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 2, p. 146 - 149
[3] Synthesis (Germany), 2015, vol. 47, # 20, p. 3169 - 3178
[4] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2455 - 2478 |
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