| Identification | More | [Name]
2-Bromo-3-nitropyridine | [CAS]
19755-53-4 | [Synonyms]
2-BROMO-3-NITROPYRIDINE
2-Bromo-3-nitropyridine ,98% | [EINECS(EC#)]
625-152-0 | [Molecular Formula]
C5H3BrN2O2 | [MDL Number]
MFCD00955613 | [Molecular Weight]
202.99 | [MOL File]
19755-53-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to cream crystalline powder | [Melting point ]
122-125 °C (lit.) | [Boiling point ]
244.0±20.0 °C(Predicted) | [density ]
1.8727 (rough estimate) | [refractive index ]
1.6200 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
-3.24±0.10(Predicted) | [color ]
Light orange to Yellow to Green | [Detection Methods]
HPLC | [BRN ]
124504 | [InChIKey]
ZCCUFLITCDHRMG-UHFFFAOYSA-N | [CAS DataBase Reference]
19755-53-4(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to cream crystalline powder | [Uses]
2-Bromo-3-nitropyridine may be used in the synthesis of the following:
- 3-nitropyridine-2-carbonitrile
- pyrrolo[3,2-b]pyridine
- 3-(hetero)arylated phenothiazines
- 7-anilino-6-azaindole-1-benznesulfonamides
| [General Description]
2-Bromo-3-nitropyridine is a pyridine derivative. It can be synthesized from 3-nitropyridine-2-amine. | [Synthesis]
General procedure for the synthesis of 2-bromo-3-nitropyridine from 2-amino-3-nitropyridine: 3-nitropyridin-2-amine (1.0 g, 7.19 mmol) was dissolved in 35 mL of DMSO, KNO2 (2.45 g, 28.75 mmol) and CuBr (0.206 g, 1.44 mmol) were added. A 48% aqueous HBr solution (3.60 mL, 32.0 mmol) dissolved in DMSO (35 mL) was slowly added dropwise to the above mixture at 35 °C. After the dropwise addition was completed, the reaction mixture was stirred at 35°C for 4 hours. Subsequently, the reaction solution was transferred to 100 mL of ice water solution containing K2CO3 (7 g). The reaction mixture was extracted with ether, the ether layer was washed with water and dried over anhydrous Na2SO4. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: 100% dichloromethane) to afford 2-bromo-3-nitropyridine as a beige powder (0.662 g, 45% yield). Thin-layer chromatography Rf value was 0.75 (dichloromethane); melting point was 121-122 °C (literature value: 123-124 °C); IR (KBr) νmax (cm-1): 3042 (νCHar), 1578 and 1562 (νC=C), 1524 (νasNO2), 1350 (νsyNO2); 1H NMR (400 MHz. DMSO-d6): δ 8.73 (dd, 1H, J1=1.6Hz, J2=4.8Hz, H-6), 8.54 (dd, 1H, J1=1.6Hz, J3=8.0Hz, H-4), 7.79 (dd, 1H, J2=4.8Hz, J3=8.0Hz, H-5); 13C NMR (100MHz, DMSO -d6): δ 153.26 (C-6), 147.08 (C-3), 134.48 (C-4), 132.08 (C-2), 124.44 (C-5); MS (ESI) m/z (%): 202.9 (100) [M+H]+, 204.9 (100) [M+H+2]+. Calculated elemental analysis (C5H3BrN2O2): C, 29.58; H, 1.49; N, 13.80. measured values: C, 29.63; H, 1.50; N, 13.83. | [References]
[1] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 171 - 183
[2] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
[3] Canadian Journal of Chemistry, 2005, vol. 83, # 3, p. 213 - 219 |
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