| Identification | Back Directory | [Name]
4-Bromo-7-azaindole | [CAS]
348640-06-2 | [Synonyms]
SW-65
SWF-65
348640-06-2
4-BroMo-7-Azaindol
4-BROMO-7-AZAINDOLE
4-broMo-1H-pyrrolo[2
4-Bromo-1H-pyrrolo-[2,3]pyridine
4-BROMO-1H-PYRROLO[2,3-B]PYRIDINE
1H-PYRROLO[2,3-B]PYRIDINE, 4-BROMO- | [EINECS(EC#)]
625-999-6 | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD08272233 | [MOL File]
348640-06-2.mol | [Molecular Weight]
197.03 |
| Chemical Properties | Back Directory | [Melting point ]
178-183℃ | [density ]
1.770±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Solid | [pka]
12.95±0.40(Predicted) | [color ]
Yellow to orange | [InChI]
InChI=1S/C7H5BrN2/c8-6-2-4-10-7-5(6)1-3-9-7/h1-4H,(H,9,10) | [InChIKey]
LEZHTYOQWQEBLH-UHFFFAOYSA-N | [SMILES]
C12NC=CC1=C(Br)C=CN=2 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale yellow powder | [Description]
4-Bromo-7-azaindole(348640-06-2) is a small molecule pyridine compound containing a bromine functional group. This substance can be used as a basic structure for the synthesis of other complex organisms. It is also a good reagent and can react with amides, amines, amino acid esters and phenolic compounds through the formation of C-N and C-O bonds.
| [Synthesis]
1H-pyrrolo[2,3-b]pyridine-7-oxide (3.0 g, 22.4 mmol) was used as starting material, which was co-dissolved with tetramethyl ammonium (4.13 g, 1.2 eq.) in N,N-dimethylformamide (DMF, 30 ml). Dimethyl sulfoxide (Ms2O, 7.8 g, 2.0 eq.) was added in batches at 0 °C. The reaction mixture was stirred at 0 °C for 1 h, then brought to room temperature and continued stirring for 4 h. The reaction was carried out at 0 °C. Upon completion of the reaction, the reaction solution was diluted with water (60 ml) and the pH was adjusted with solid sodium hydroxide (NaOH) to 7. Subsequently, more than 130 ml of water was added and the resultant suspension was kept at 5 °C for 1 h. The reaction was carried out by filtration. The precipitate was collected by filtration, washed with ice water (2 x 20 ml) and dried in a vacuum oven using phosphorus pentoxide (P2O5) as a desiccant to give finally 4-bromo-1H-pyrrolo[2,3-b]pyridine (2.47 g, 56% yield). Mass spectrum (ESI) m/z 196.9 [M + H]+. 1H NMR (400 MHz, CDCl3) δ 10.77 (br s, 1H), 8.14 (d, J = 5.2 Hz, 1H), 7.42 (s, 1H), 7.31 (d, J = 5.1 Hz, 1H), 6.57 (s, 1H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1208 - 1212
[2] Patent: CN101921268, 2016, B. Location in patent: Paragraph 0257; 0265-0268
[3] Patent: WO2010/30727, 2010, A1. Location in patent: Page/Page column 120
[4] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[5] Patent: WO2009/140320, 2009, A1. Location in patent: Page/Page column 86 |
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