| Identification | More | [Name]
5-Bromo-7-azaindole | [CAS]
183208-35-7 | [Synonyms]
5-BROMO-1H-PYRROLO[2,3-B]PYRIDINE
5-BROMO-7-AZAINDOLE
5-BROMO AZAINDOLE
1H-Pyrrolo[2,3-b]pyridine, 5-bromo-
5-Bromo-1H-pyrrolo2,3-büpyridine | [EINECS(EC#)]
629-247-8 | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD06659677 | [Molecular Weight]
197.03 | [MOL File]
183208-35-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
176-180 °C | [Boiling point ]
357.4±42.0 °C(Predicted) | [density ]
1.79±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
6.25±0.20(Predicted) | [color ]
White to yellow | [InChI]
InChI=1S/C7H5BrN2/c8-6-3-5-1-2-9-7(5)10-4-6/h1-4H,(H,9,10) | [InChIKey]
LPTVWZSQAIDCEB-UHFFFAOYSA-N | [SMILES]
C12NC=CC1=CC(Br)=CN=2 | [LogP]
1.8 at 25℃ and pH7 | [CAS DataBase Reference]
183208-35-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Acetic acid-->Government regulation-->ZINC-->tert-Butanol-->Boron trifluoride diethyl etherate-->7-Azaindole-->Manganese triacetate dihydrate-->1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]--->Acetamide, N-[5-bromo-3-[2-(trimethylsilyl)ethynyl]-2-pyridinyl]--->5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE-->3,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one-->2-Aminopyrrole-->5-bromo-3-ethynylpyridin-2-amine-->Methyl 5-bromo-7-azaindole-3-carboxylate-->5-BROMO-3-((TRIMETHYLSILYL)ETHYNYL)PYRIDIN-2-AMINE-->5-BROMO-2,3-DIHYDRO-1H-PYRROLO[2,3-B]PYRIDINE-->4-(2-amino-5-bromo-pyridin-3-yl)-2-methyl-but-3-yn-2-o | [Preparation Products]
1-PropanesulfonaMide, N-[3-[[5-broMo-1-(2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl]-2,4-difluorophenyl]- |
| Hazard Information | Back Directory | [Chemical Properties]
White to light brown powder or crystal | [Uses]
5-Bromo-7-azaindole is a chemical reagent used in organic syntheses. Used in the synthesis of Venetoclax (A112430), a potent and selective BCL-2 inhibitor that achieves potent antitumour activity while sparing platelets. Also used in other 7-azaindole derivatives such as for PDK1 inihibtors. | [Synthesis]
In the 250 ml flask is sequentially added in 50 ml ethanol and 5-bromo-1-hydrogen pyrrolo [2,3 - the b] pyridine -2 - ketone (4.2g, 20
mmol), Sn powder (4.7 g, 40 mmol) and 5 mol/L hydrochloric acid (14 ml),
40 ℃ stirring for 2 hours, the reaction is completed, to remove the
ethanol, add 50 ml of water residue is completely dissolved,
saturated NaHCO3 solution and to pH=8, and filtering the resulting solid,
after drying, dissolved in 50 ml chloroform, adding CuBr2(13.4 g,
60mmol), 60 Cstirring for 2 hours, the reaction is completed, the end of
the reaction, rotary evaporated to remove chloroform, adding 50 ml
saturated NaHCO3 solution, ethyl acetate (3 × 100 ml), the combined
organic phase with water (50 ml) for washing and then the saturated salt
water (50 ml) washing, anhydrous Na2SO4 drying, filtering, the filtrate
is concentrated to obtain 5-bromo-1H-pyrrolo [2,3 - the b]
pyridine the crude product, the crude product is chloroform: hexane=2:1
(volume ratio) mixed solution recrystallize to get 3.1 g of pale yellow 5-Bromo-7-azaindole pure product, yield
77.6%, melting point:176.8-177.3 ℃. | [Solubility in organics]
The solubility of 5-Bromo-7-azaindole in pure solvents increases with increasing temperature. Among them 5-Bromo-7-azaindole showed the best solubility in methyl acetate and the worst solubility in hexane. The maximum change in solubility of 5-Bromo-7-azaindole in DCM was observed at T = 298.15-313.15 K. The solubility of 5-Bromo-7-azaindole in DCM was found to be the most variable. |
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