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CAS No. : | 73290-22-9 | MDL No. : | MFCD03095201 |
Formula : | C5H3BrIN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LLKRSJVPTKFSLS-UHFFFAOYSA-N |
M.W : | 283.89 | Pubchem ID : | 4738271 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.65 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.24 cm/s |
Log Po/w (iLOGP) : | 2.02 |
Log Po/w (XLOGP3) : | 2.53 |
Log Po/w (WLOGP) : | 2.45 |
Log Po/w (MLOGP) : | 2.18 |
Log Po/w (SILICOS-IT) : | 3.09 |
Consensus Log Po/w : | 2.45 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.75 |
Solubility : | 0.0506 mg/ml ; 0.000178 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.45 |
Solubility : | 1.01 mg/ml ; 0.00357 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.82 |
Solubility : | 0.0427 mg/ml ; 0.00015 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.39 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: With hydrogen bromide; bromine; sodium nitrite In water at 0 - 15℃; Stage #2: With sodium hydroxide In water |
Bromine (3ml) was added dropwise to a solution of 2-amino-5-iodo-pyridine (5g, 20mmol) in 48percent hydrobromic acid in water (10ml). AIL ice bath was used to cool the system. Sodium nitrite (3.4 g in 5ml of water) was then added dropwise so that the temperature does not go above 15°C. After the addition was complete, sodium hydroxide (16g) in water (40ml) was added. Brown solid precipitated and was extracted with DCM (50ml). The DCM extract was washed with water, brine, dried over MgS04 and evaporated in vacuo to give 2-bromo-5-iodo-pyridine (4.4g, 78percent). |
65.23% | With hydrogen bromide; bromine; sodium nitrite In water at 0 - 20℃; for 1 h; | To a solution of 5-iodopyridin-2-amine(0.7 g, 3.18 mmol) in HBr [(1.26 g, 15.6 mmol (48percent in water)] at 0 00 sodium nitrite (0.746 g, 10.82 mmol) in water was added drop wise, followed by addition of bromine (1 .71 g, 10.82 mmol). The reaction mixture was kept at room temperature for 1 h. The reaction mixture was quenched with NaOH solution and extracted with ethyl acetate, washed with water, and dried overanhydrous Na2SO4. The solvent was removed under vacuo. The crude product was purified by column chromatography to yield title compound (0.6 g, 65.23percent) as a white solid. LCMS: (M+H) = 284; 1H NMR: (DMSO-d6, 300MHz) 6 8.64-8.65 (d, 1 H), 8.09- 8.12 (dd, 1H), 7.50-7.53 (m, 1H). |
65.23% | With hydrogen bromide; bromine; sodium nitrite In water at 0 - 20℃; for 1 h; | To a solution of 5-iodopyridin-2-amine (0.7 g, 3.18 mmol) in HBr [(1.26 g, 15.6 mmol(48percent in water)] at 000 sodium nitrite (0.746 g, 10.82 mmol) in water was added dropwise followed by addition of bromine (1 .71 g, 10.82 mmol). The reaction mixture was at room temperature for 1 h. The reaction mixture was quenched with NaOH solution and extracted with ethyl acetate, washed with water, and dried over anhydrous Na2SO4 The solvent was removed under vacuo. The crude product was purified bycolumn chromatography to yield title compound (0.6 g, 65.23percent) as a white solid. LOMS: (M+H) = 284; 1H NMR: (DMSO-d6, 300MHz) 6 8.64-8.65 (d, 1H), 8.09-8.12 (dd, 1 H), 7.50-7.53 (m, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24 h; | General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol,), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were placed in a closed tube with a rubber stopper. The mixture was reacted at room temperature equipped with an air balloon for 24 h. The resulting suspension was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness. The crude product was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate = 20: 1 (v/v) as eluent to give 0.086 g of 2j as a light yellow solid (0.35 mmol, 87percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: With n-butyllithium In diethyl ether at -78℃; Stage #2: for 1 h; Stage #3: With hydrogenchloride; water In diethyl ether at 20℃; |
Preparation of 2-Bromo-5-formylpyridine (8)The compound was prepared following the literature procedure [van den Heuvel et al J. Org. Chem. 2004, 69, (2), 250-262.]. To a suspension of 2-bromo-5-iodopyridine (3 g, 11 mmol) is dry Et2O (10O mL) at -78 0C was added /1-BuLi (2.2 M, 5.3 mL, 1.1 eq). The reaction mixture was stirred for 1 h prior to the addition of dry DMF (1 mL). After stirring for an additional 1 h, the mixture was warmed to room temperature and quenched by the addition of dilute HCI (1 M, 20 mL). The organic layer was separated, and the aqueous layer was further extracted with Et2O (2 x 20 mL). The combined organic fraction was dried with MgSO4, filtered, and the solvent removed in vacuo. Column chromatography on silica using a gradient (7-60percent EtOAc, hexanes) yielded the product as a white solid (1.25 g, 64percent yield). Rf (1 : 1 EtOAc/hexanes): 0.39. Mp 100-101 0C. (lit. 100 0C). 1H NMR (CDCI3): δ 7.69 (d, J = 8 Hz, 1H), 8.01 (dd, J = 8 Hz and 2 Hz, 1H), 8.83 (d, J = 2 Hz, 1H), 10.10 (s, 1H1 CHO). |
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