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CAS No. : | 71838-16-9 | MDL No. : | MFCD00079718 |
Formula : | C7H6BrI | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PLAKKSAFIZVHJP-UHFFFAOYSA-N |
M.W : | 296.93 | Pubchem ID : | 626634 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.82 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
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) : | -5.53 cm/s |
Log Po/w (iLOGP) : | 2.53 |
Log Po/w (XLOGP3) : | 3.63 |
Log Po/w (WLOGP) : | 3.36 |
Log Po/w (MLOGP) : | 4.25 |
Log Po/w (SILICOS-IT) : | 3.95 |
Consensus Log Po/w : | 3.54 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.46 |
Solubility : | 0.0103 mg/ml ; 0.0000346 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.32 |
Solubility : | 0.143 mg/ml ; 0.000481 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.58 |
Solubility : | 0.00786 mg/ml ; 0.0000265 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.03 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
92% | Stage #1: With hydrogenchloride; sodium nitrite In water; acetonitrile at 0 - 5℃; for 0.5 h; Stage #2: With potassium iodide In water; acetonitrile at 20℃; |
General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 °C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 °C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere; | General procedure: Et2NH (20 mL), THF (20 mL), 1-bromo-2-iodobenzene (2.2 mL g,18 mmol), and trimethylsilylacetylene (2.9 mL, 21 mmol) weresuccessively added to a flask containing PdCl2(PPh3)2 (0.25 g,0.35 mmol) and CuI (0.067 g, 0.35 mmol). The mixture was stirredat room temperature for 12 h and then evaporated. The residuewasdiluted with hexane/AcOEt (5:1) and washed with 1M aqueousHCl. The organic layer was dried over Na2SO4 and evaporated. Purificationof the residue by silica-gel column (hexane) gave 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzene [38274-16-7] (1a?) asa pale yellow clear liquid (4.12 g, 16.3 mmol, 92% yield).nBuLi (2.65M in hexane, 701 mL, 1.86 mmol) was added to astirred solution of 1a? (472 mg, 1.86 mmol) in THF (4 mL) at 78 C.After 0.5 h, Me2SiCl2 (223 mL, 1.86 mmol) was added to the mixtureat that temperature. Then the mixture was warmed to room temperatureand stirred for 2 h. MeOH (0.5 mL) and Et3N (290 mL,2.08 mmol) were successively added to the reaction mixtureat 78 C. After removing the cooling bath, the resultant mixturewas stirred at room temperature for 1 h. The mixturewas quenchedwith water and extracted with hexane/AcOEt (30:1) three times.The combined organic layer was dried over Na2SO4 and evaporated.The residuewas purified by flash column chromatography (hexane/AcOEt 40:1). The title compound,1-(methoxydimethylsilyl)-2-[2-(trimethylsilyl)ethynyl]benzene (1a), was obtained as a pale yellowliquid (0.721 g, 2.75 mmol, 71% yield). 1H NMR (500 MHz, CDCl3,7.26 ppm) d 0.25 (s, 9H), 0.47 (s, 6H), 3.56 (s, 3H), 7.30e7.34 (m, 2H),7.48e7.50 (m, 1H), 7.59e7.61 (m, 1H); 13C NMR (125 MHz, CDCl3,77.0 ppm) d 1.8, 0.3, 50.9, 96.9, 106.4, 127.7, 127.7, 129.2, 132.8,134.0, 140.8; IR (neat) 3073, 3052, 2959, 2831, 2155, 1429 cm1;HRMS (EI) calcd for C14H22OSi2 [M] 262.1209, found 262.1209.The substrates 1b-l, and 1p were synthesized by the samemanner as described for the preparation of 1a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | [(2-Bromo-4-methyl~phenyl)-difluoromethyl]-phosphonic acid diethyl ester (D): To activated zinc (12g, 190 mmol) in DMA (70 mL) was added bromodifluoromethyldiethyl-phosphonate (50g, 190mmol) in DMA (70 mL). The resulting mixture was stirred at 45 C for 3 hours, after which copper (I) bromide (27g, 190 mmol) was added and stirring was continued for 0.5 hours at room temperature. 3-Bromo-4-iodotoluene (28g, 94mmol) was then added and the mixture was sonicated at room temperature for 12 hours. The reaction mixture was partitioned between ether and H2O, filtered through Celite, and the organic layer was dried over MgSO4 and concentrated in vacuo to yield 21g (63%) of a clear, colorless oil. | |
63% | To activated zinc (1.2g, 19mmol) in DMA (7mL) was added bromodifluoromethyldiethyl-phosphonate (5.0g, 19mmol) in DMA (7mL). The resulting mixture was stirred at 450C for 3 hours, after which copper (I) bromide (2.7g, 19mmol) was added and stirring was continued for 0.5 hours at room temperature. 3-Bromo-4-iodotoluene (2.8g, 9.4mmol) was then added and the mixture was sonicated at room temperature for 12 hours. The reaction mixture was partitioned between ether and H2O, filtered through Celite, and the organic layer was dried over MgSO4 and concentrated in vacuo to yield 2.1g (63%) of a clear, colorless oil. 1HNMR (300 MHz, CDCl3) delta 7.51 (d, J= 6 Hz, 1 H), 7.27 (s, 1 H), 7.20 (d, J- 7.5 Hz, 1 H), 4.27 (m, 4 H), 1.36 (t, J= 8.1 Hz). | |
The cadmium reagent was generated as in Example 1 using Cd metal (8.5 g, 0.075 mole), diethyl bromodifluoromethylphosphonate (18 g, 0.068 mole) and AcOH (1.0 niL) in DMF (80 mL). A 40 mL aliquot of this solution was added to CuCl (6.72 g, 0.068 mole) followed after 2 minutes by the addition of <strong>[71838-16-9]3-bromo-4-iodotoluene</strong> (5.0 g, 0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with additional ether (300 mL) and the combined ether layer was washed with saturated ammonium chloride (500 mL) and water (500 mL) then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/ hexanes afforded 4.4 g of (2-bromo-4-methyl-phenyl)difluoromethylphosphonic acid diethyl ester. To the diethyl ester material obtained, (1.8 g, 0.005 mole) in carbon tetrachloride (CCl4, 30 mL), were added AIBN (0.033 g, 0.0002 mole) and N- bromosuccinimide (NBS, 0.89 g, 0.005 mole). The reaction was heated at reflux for 2 hours (a thin white suspension formed). The reaction was allowed to reach room temperature and the solvent was removed under vacuum. The residue was taken up in ethyl acetate (EtOAc, 120 mL) and washed with saturated NaHCtheta3 (60 mL) and brine (60 mL) then dried over MgSO4. Filtration and solvent evaporation afforded 2.1 g of crude product. Flash chromatography on silica gel using 20-30% ethyl acetate/hexanes afforded 1.11 g of (2- bromo-4-bromomethyl-phenyl)-difluoro-methylphosphonic acid diethyl ester.; Example 25 - Synthesis of Compound 25(2-Bromo-4-methylphenyl) difluoromethylphosphonic acid diethyl ester 25 To a suspension of 8.5 g Cd metal (0.075 mole), in 80 mL DMF (dried over 4A molecular sieves for 24 hours) was added 18 g of diethyl bromodifluoro-methylphosphonate (0.068 mole) and 1 mL glacial acetic acid. Within 4 minutes an exotherm started and lasted EPO <DP n="54"/>? for 20 minutes. The suspension was stirred for 3 hours and allowed to stand at room temperature for 30-40 minutes. A 40 mL aliquot of this solution was added to 6.72 g of CuCl (0.068 mole) followed after 2 minutes by the addition of 5 g of <strong>[71838-16-9]3-bromo-4-iodotoluene</strong> (0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with 300 mL of ether and the combined ether layer was washed with 500 mL of saturated ammonium chloride and 500 mL of water, then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/hexanes afforded 4.4 g of Compound 25. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 80℃; for 18h; | To <strong>[71838-16-9]3-bromo-4-iodotoluene</strong> (14g ; 47.15mmol) and 4-(trifluoromethyl)benzeneboronic acid (9.85g ; 51.8mmol) in 1,4-dioxan (100ml) and saturated sodium carbonate solution (40ml) under nitrogen was added [l,l'-bis(diphenylphosphino)ferrocene]palladium(II) chloride (1.73g ; 2.36mmol). The reaction mixture was heated at 800C for 18h, diluted with water and ethyl acetate and filtered through hyflo. The filtrate was separated, the organic extracts were combined, washed with brine, dried over magnesium sulphate filtered and evaporated under reduced pressure to give an oil. The oil was absorbed onto silica and purified by flash chromatography using iso-hexane as eluant. The appropriate fractions were combined and evaporated under reduced pressure to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | [(2-Bromo-4-methyl-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester: A solution of (bromo-difluoro-methyl)-phosphonic acid diethyl ester (25.00 g, 93.6 mmol) in N,N-dimethylacetamide (50 mL) was added drop wise into a suspension of activated zinc (6.12 g, 93.6 mmol) under Argon. The reaction was initiated by heating and kept under 50 C. After the mixture was stirred for 3 h, copper (I) bromide (13.43 g, 93.6 mmol) was added and stirred for 1 h. A solution of 2-bromo-l-iodo-4-methyl-benzene (11.88 g, 40.0 mmol) in N,N-dimethylacetamide (25 mL) was added slowly to the reaction mixture. The resulting suspension was then stirred at room temp for 18 h. Water (100 mL) was added to the reaction mixture and the solution filtered through celite. The filtrate was diluted with EtOAc (250 mL) and organic layer was washed with H20 (50 mL), NaHC03 (5%, 50 mL) and H20 (50 mL). The solvent was removed and the residue was purified by column chromatography on silica gel, eluting with hexanes/EtOAc (4:1) to provide a colorless oil (11.75 g, 82%): .H NMR (300 MHz, CDC13) 8 7.51 (d, 1H), 7.49 (s, 1H), 7.19 (d, 1H), 4.26 (m, 4H), 2.36 (s, 3H), 1.48 (s, 9H), 1.37 (m, 6 H). | |
63% | To activated Zn (1.2g, 19mmol) in DMA (7mL) was added bromodifluoromethyldiethyl- phosphonate (5.0g, 19mmol) in DMA (7mL). The resulting mixture was stirred at 45C for 3 hours, after which copper(I) bromide (2.7g, 19mmol) was added and stirring was continued for 0.5 hours at room temperature. 3-Bromo-4-iodotoluene (2.8g, 9.4mmol) was then added and the mixture was sonicated at room temperature for 12 hours. The reaction mixture was partitioned between ether and H2O, filtered through Celite, and the organic layer was dried over MgSO4 and concentrated in vacuo to yield 2.1 g (63%) of 27 as a clear, colorless oil;1H NMR (300 MHz, CDCl3) delta 7.51 (d, J = 6 Hz, 1 H), 7.27 (s, 1 H), 7.20 (d, J= 7.5 Hz, 1 H), 4.27 (m, 4 H), 1.36 (t, J = 8.1 Hz) |
Tags: 71838-16-9 synthesis path| 71838-16-9 SDS| 71838-16-9 COA| 71838-16-9 purity| 71838-16-9 application| 71838-16-9 NMR| 71838-16-9 COA| 71838-16-9 structure
[ 869500-07-2 ]
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[ 26670-89-3 ]
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[ 260558-15-4 ]
4-Bromo-2-iodo-1-methylbenzene
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Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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