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CAS No. : | 827-08-7 | MDL No. : | MFCD00039209 |
Formula : | C6Br2F4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IPLUWQPTPKNBRD-UHFFFAOYSA-N |
M.W : | 307.87 | Pubchem ID : | 70007 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.67 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.54 cm/s |
Log Po/w (iLOGP) : | 2.15 |
Log Po/w (XLOGP3) : | 3.71 |
Log Po/w (WLOGP) : | 5.45 |
Log Po/w (MLOGP) : | 5.46 |
Log Po/w (SILICOS-IT) : | 4.94 |
Consensus Log Po/w : | 4.34 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.46 |
Solubility : | 0.0108 mg/ml ; 0.000035 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.4 |
Solubility : | 0.122 mg/ml ; 0.000397 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.2 |
Solubility : | 0.00192 mg/ml ; 0.00000625 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.77 |
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 |
---|---|---|
In n-butyllithium; diethyl ether; chloroform-d1; hexane; water; pentane; | EXAMPLE 1 Synthesis of 2,2'-dibromooctafluorobiphenyl 10 g of <strong>[827-08-7]1,2-dibromotetrafluorbenzene</strong> (32 mmol) together with 100 ml of diethyl ether are placed in a reaction vessel and cooled to -78 C. 15 ml of n-butyllithium (2.5 M in hexane) are added dropwise and the mixture is stirred for 1 hour. An excess of titanium tetrachloride is subsequently added and the mixture is stirred for another 4 hours at -78 C. The suspension is allowed to warm to room temperature and is stirred for another 10 hours. It is then hydrolyzed using H2O. The aqueous phase is shaken a number of times with diethyl ether and the organic phases are subsequently combined and dried over magnesium sulfate. The solvent is taken off and the residue is recrystallized from a 1:1 mixture of diethyl ether/n-pentane. 19F-NMR CDCl3: -127.5 ppm (m, 2F, 3,3'-F), -134.6 ppm (m, 2F, 6,6'-F), -149.9 ppm (m, 2F, 4,4'-F), -154.3 ppm (m, 2F, 5,5'-F) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Butyllithium (1.6 M in hexanes, 12.6 mL, 20.16 mmol) was added dropwise to a stirred solution of <strong>[827-08-7]1,2-<strong>[827-08-7]dibromotetrafluorobenzene</strong></strong> (2.6 g, 8.44 mmol) in ether (50 mL) at -78 C. After 2 hours this solution was slowly added to a pre-cooled solution (-78 C.) of trimethylborate (2.3 mL, 20.52 mmol) in ether (25 mL). The resulting suspension was stirred at -78 C. for two hours then gradually warmed to room temperature and hydrolyzed with 20 mL of 10% HCl. The yellow organic phase was separated and the aqueous phase was extracted with dichloromethane (3*15 mL). The combined organic phases were washed with water (3*10 mL) and dried over magnesium sulfate. Removal of solvent under reduced pressure gave a yellow oil that was recrystallized from water at a pH of 4 to afford a crystalline solid. (1.5 g, 75%) 19F NMR (D2O/HCl) delta: -136.6 (d, JF-F=28.3 Hz, 2F, C6F4), -156.5 (d, JF-F=28.3 Hz, 2F, C6F4). 11B NMR (D2O/HCl) delta: 16.9 (br). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; ethyl acetate; toluene; | Step 1 Preparation of 1,2,3,4-tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene Under nitrogen, 1 g of Pd(PPh3)4 was added to a stirred solution of 4.85 g (15.8 mmol) of <strong>[827-08-7]1,2-dibromo-3,4,5,6-tetrafluorobenzene</strong> (Aldrich), 2.65 g (18.9 mmol) of 4-fluorophenylboronic acid, and 3.17 g (18.9 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) in 80 mL of toluene, 50 mL of ethanol, and 35 mL of 2M Na2 CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed water, and dried over Na2 SO4. Concentration in vacuo gave 7.3 g of 1,2,3,4-tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene as a yellow oil which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In hexane; | EXAMPLE 1 1,4-bis(dipentafluorophenylboryl)-2,3,5,6-tetrafluorobenzene 1.54 g (5 mmol) of <strong>[827-08-7]dibromotetrafluorobenzene</strong> are dissolved in 40 ml of n-hexane and cooled to -78 C. 6.4 ml of n-BuLi (10 mmol) are slowly added dropwise to the solution and the mixture is stirred for 1 hour. Subsequently, 1.90 g (5 mmol) of bis(pentafluorophenyl)borylchloride are dissolved in 40 ml of n-hexane and likewise added dropwise to the above solution. The suspension obtained is slowly warmed to room temperature, forming a white precipitant. This is separated off by filtration and the filtrate obtained is evaporated to dryness under reduced pressure. The yield of the resulting 1,4-bis(dipentafluorophenylboryl)-2,3,5,6-tetrafluorobenzene obtained as a yellow oil is 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | To a cooled solution of 1,2-Dibromotetrafluorobenzene (5.00 g, 16.2 mmol, 1.00 equiv) in Et20 (162 mL) at -78 C was added n-BuLi (7.75 mL, 2.10 M in hexanes, 16.2 mmol, 1.00 equiv) dropwise over 30 mm under N2. The reaction mixture was stirred for another 30 minutes before pentanal (1.90 mL, 17.9 mmol, 1.10 equiv) was added dropwise. The reaction mixture was stirred for 5 h at -78 C before it was warmed to 0 C and quenched with H2O (75 mL). The aqueous phase extracted with Et2O (3 x 30 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. Flash chromatography (2% to 5% ethyl acetate in hexanes) provided 4.34 g (85% yield) of the perfluorinated bromo benzylic alcohol. | |
85% | To a cooled solution of 1,2-Dibromotetrafluorobenzene (5.00 g, 16.2 mmol, 1.00 equiv) in Et20 (162 mL) at -78 C was added n-BuLi (7.75 mL, 2.10 M in hexanes, 16.2 mmol, 1.00 equiv) dropwise over 30 mm under N2. The reaction mixture was stirred for another 30 minutes before pentanal (1.90 mL, 17.9 mmol, 1.10 equiv) was added dropwise. The reaction mixture was stirred for 5 h at -78 C before it was warmed to 0 C and quenched with H20 (75 mL). The aqueous phase extracted with Et20 (3 x 30 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. Flash chromatography (2% to 5% ethyl acetate in hexanes) provided 4.34 g (85% yield) of the perfluorinated bromo benzylic alcohol. |
Tags: 827-08-7 synthesis path| 827-08-7 SDS| 827-08-7 COA| 827-08-7 purity| 827-08-7 application| 827-08-7 NMR| 827-08-7 COA| 827-08-7 structure
[ 811713-01-6 ]
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[ 811713-01-6 ]
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[ 811713-80-1 ]
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[ 139215-43-3 ]
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[ 811713-01-6 ]
1,2-Dibromo-3,4-difluorobenzene
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[ 811713-80-1 ]
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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