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CAS No. : | 112671-42-8 | MDL No. : | MFCD11505492 |
Formula : | C6H3BrINO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLUAZLDTZYHVSO-UHFFFAOYSA-N |
M.W : | 327.90 | Pubchem ID : | 13803666 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.68 |
TPSA : | 45.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.11 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 3.09 |
Log Po/w (WLOGP) : | 2.96 |
Log Po/w (MLOGP) : | 3.35 |
Log Po/w (SILICOS-IT) : | 1.35 |
Consensus Log Po/w : | 2.52 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.16 |
Solubility : | 0.0228 mg/ml ; 0.0000696 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.72 |
Solubility : | 0.0625 mg/ml ; 0.000191 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.55 |
Solubility : | 0.0916 mg/ml ; 0.000279 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.48 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
88% | Stage #1: With boron trifluoride diethyl etherate In tetrahydrofuran at -30℃; for 0.5 h; Stage #2: With tert.-butylnitrite In tetrahydrofuran; diethyl ether at -30 - -5℃; for 1.25 h; Stage #3: With iodine; potassium iodide In acetonitrile at 20℃; for 1.3 h; |
To BF3·OEt2 (16.0 mL, 126.3 mmol) at –30 °C was added a solution of 4-bromo-2-nitroaniline (6.50g, 30.0 mmol) in THF (100 mL) dropwise over 20 min. The mixture was stirred at –30 °C for 10 min andthen a solution of tBuONO (13.0 mL, 90percent, 109.3 mmol) in THF (81 mL) was added dropwise over 15min. The reaction mixture was allowed to warm to –10 °C at which time Et2O (158 mL) was addeddropwise. The mixture was allowed to stir at –5 °C for 1 h until a white pale solid precipitated. The solidwas filtered and washed with Et2O to afford a white solid which was then added in one portion to a 500mL round-bottomed flask containing, KI (5.45 g, 26.53 mmol), iodine (7.16 g, 13.27 mmol), and MeCN(120 mL). The mixture was stirred at RT for 1.3 h, quenched with sat. aq Na2S2O3 (250 mL), and22extracted with CH2Cl2 (2 x 150 mL). The organic layers were combined, dried over Na2SO4, andconcentrated in vacuo to afford 4-bromo-1-iodo-2-nitrobenzene (8.61 g, 88percent yield) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With iron; acetic acid In ethanol at 100℃; for 1.3 h; | To a solution of 4-bromo-1-iodo-2-nitrobenzene (8.38 g, 109.6 mmol) in AcOH (45 mL) and EtOH(45 mL) at RT was added Fe (6.12 g, 109.6 mmol). The mixture was stirred at 100 °C for 1.3 h andcooled to RT. The reaction mixture was diluted with Et2O (90 mL) and washed with sat. aq. NaHCO3(200 mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3 x 60 mL).The organic layers were combined, washed with brine (300 mL), dried over Na2SO4, and concentrated invacuo. The residue was purified by flash chromatography (silica gel, hexane/AcOEt = 19:1) to afford 5-bromo-2-iodoaniline 30b (6.89 g, 91percent yield) as a light yellow solid. |
39 g | With tin(ll) chloride In methanol at 0 - 80℃; for 4 h; | To a solution of 4-bromo-1 -iodo-2-nitrobenzene (66 g, 0.2 mol) in MeOH (700 mL) was added stannous chloride (226 g, 1 mol) at 0 °C. The resultant mixture was heated to reflux (80 °C) for 4 h. The solvent was removed under reduced pressure, and then the residue was diluted with ethyl acetate (1 L), washed with H2O (1 L), dried over sodium sulfate, concentrated to give a residue which was purified by column chromatography (eluent: petroleum ether: ethyl acetate= 20:1 ) to give 5-bromo-2-iodoaniline (39 g, 65percent) as a white solid. LCMS (Method B): 2.27 min m/z [MH]+=298.1 ; 300.1 |
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