Structure of 873-75-6
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CAS No. : | 873-75-6 |
Formula : | C7H7BrO |
M.W : | 187.03 |
SMILES Code : | OCC1=CC=C(Br)C=C1 |
MDL No. : | MFCD00004650 |
InChI Key : | VEDDBHYQWFOITD-UHFFFAOYSA-N |
Pubchem ID : | 70119 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.03 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.15 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.3 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.37 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.93 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.15 |
Solubility | 1.32 mg/ml ; 0.00706 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.17 |
Solubility | 12.7 mg/ml ; 0.0677 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.08 |
Solubility | 0.156 mg/ml ; 0.000832 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.62 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
76% | With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 2h;Heating / reflux; | 5-iso-Butyl-2- (N-tert-butylaminosulfonyl) thiophene-3-boronic acid (319.3 mg, 1.00 mmol; see Example L (c) above), 4-bromobenzyl alcohol (374.1 mg, 2.00 mmol), toluene (20 mL), ethanol (4 ML), NAOH (1. OM, 4 mL, 4 mmol) and Pd (PPh3) 4 (34 mg, 0. 030MMOL) were mixed together under N2. The mixture was warmed to reflux for 2 hours and was then diluted with EtOAc (50 mL), washed with water and brine and dried over MGS04. The solvent was removed and the residue was separated by column chromatography using CHCL3 : MeOH (40: 1) as eluent to give 289 mg of the sub-title compound (yield: 76%). IR (neat): 3465, 3162,2952, 2867,1441 CM' LH NMR 8 (CD30D): 7.59 (2H, d, J= 8. 2 Hz), 7.45 (2H, d, J= 8.2 Hz), 6.75 (1H, s), 4.75 (2H, s), 4.11 (1H, brs), 2.69 (2H, d, J= 7.1 Hz), 1.92 (1H, m), 0.99 (6H, d, J= 7.2 Hz), 0.98 (9H, s) 3C NMR 8 (CD30D): 148.3, 142.9, 141.1, 134.2, 130.3, 128.9, 127. 6, 126.8, 64. 8, 54.5, 39.2, 30.5, 29.5, 22.1 MS (EI+) m/z: 382.0 Anal. Calcd. for CLGH27NO3S2 : C, 59.8 ; H, 7.3 ; N, 3.7. Found: C, 59.6 ; H, 7.0 ; N, 3.5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h; | A typical synthetic procedure is as follows. 1,7-dibromo perylene diimide (1, 77 mg, 0.1 mmol) was dissolved into 5 mL of dimethylformamide (DMF). To which alkyl alcohol (R-OH, 0.5 mmol) and potassium carbonate (K2CO3, 70 mg, 0.5 mmol) were added. The resulted mixture was then allowed reacted under 80C for 1-4 hours. The reaction mixture was then powered into 15 mL water and the red solid was then re-dissolved in 20 mL dichloromethane (DCM) and washed with 1N hydrochloric acid and then water each for 3 times. Then, DCM layer was dried over Na2SO4. After removal of DCM, the residue was applied to chromatography with CH2Cl2/ethyl acetate (100:0-100:2) as eluents to afford the desired products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In water; dimethyl sulfoxide; at 85℃; for 18h;Inert atmosphere; | The compound 1(1 eq, 0.53 mmol) was dissolved in DMSO (2 mL) followed by the addition of potassium acetate (3 eq, 1.59 mmol), bis(pinacolato)diboron (1.1 eq, 0.59 mmol) and Pd(dppf)Cl2 (0.2 eq, 0.11 mmol). The mixture was deoxygenated by three successive argon bubbling/vaccum cycles. The reaction was then heated at 85C under argon for 18h. Water (5 mL) was added and the resulting black solution was extracted 3 times with EtOAc (3 x 10 mL). The combined organic extracts were washed with brine, dried, filtered and evaporated under vaccum. The resulting paste was purified using column chromatography (silica gel, 70/30 Hex/EtOAc) to afford the desired compound (Rf = 0.3) as a colourless oil (113 mg, 91%). 1H-NMR (CDCI3, 600 MHz) delta 7.79 (d, J = 7.7 Hz, 2H), 7.36 (d, J = 7.7 Hz, 2H), 4.71 (s, 2H), 1.35 (s, 12H); 13C-NMR (CDC13, 150 MHz) delta 144.1, 135.2, 126.2, 83.9, 65.4, 25.0. |
90% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 85℃;Inert atmosphere; | p-Bromobenzyl alcohol (Compound 1, 1.0 g, 5.35 mmol) was dissolved in 10 mL of dry 1,4-dioxane solution, and boranoic acid pinacol ester (247 mg, 5.88 mmol), potassium acetate and pdCl 2 ( Dppf), under N2 protection, heat to 85 C to stir the reaction. After the reaction was completed by thin layer chromatography, the solvent was evaporated under reduced pressure, and ethyl acetate (200 ml) was added and thenThe organic phase was dried over anhydrous sodium sulfate and concentrated under reduced vacuo.The crude product was purified by column chromatography (mobile phase ethyl acetate: petroleum ether = 1:8-1:4)Obtained 181 mg of a pale yellow oily liquid with a yield of 90%. |
With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 80℃; for 24h;Inert atmosphere; | Under an argon atmosphere, (4-bromophenyl)methanol (3.0 g) and bis(pinacolato)diboron (4.5 g) was dissolved in dioxane (35 ml), and dichlorobis(triphenylphosphine)palladium(II) (567 mg) and potassium acetate (4.7 g) were added thereto, followed by stirring at 80 C. for 1 day. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was dissolved in DME (35 ml) and water (18 ml), and tert-butyl {2-[(3-bromobenzyl)(methyl)amino]-2-oxoethyl}carbamate (3.5 g) was added thereto under an argon atmosphere. In addition, sodium carbonate (3.1 g) and tetrakis(triphenylphosphine)palladium (339 mg) were added thereto, followed by stirring at 70 C. for 1 day. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl {2-[[4'-(hydroxymethyl)biphenyl-3-yl]methyl}(methyl)amino]-2-oxoethyl}carbamate (2.8 g). |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 6h;Inert atmosphere; | (3) 1 g of 1- (4-bromobenzene) ethanol was dissolved30 ml 1,4-dioxane solution,Two equivalents of bis (pinacolato) diboron,3 equivalents of potassium acetate,5% equivalent of [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride Under argon atmosphere at 80 C,After 6 hours of reaction, the product was obtained by column chromatography. | |
1500 mg | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 16h; | A mixture of (4-bromophenyl)methanol (1 g, 5.35 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (4.07 g, 16.04 mmol), KOAc (1.05 g, 10.69 mmol) and Pd(dppf)Cl2.CH2Cl2 (873.27 mg, 1.07 mmol) in 1,4-Dioxane (20 mL) was stirred at 90 C for 16 hours. After cooling to r.t., the mixture was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0 to 50%) to give the product (1500 mg) as oil. H NMR (400MHz DMSO-d6) _ = 7.63 (d, 2H), 7.32 (d, 2H), 5.23 (t, 1H), 4.51 (d, 2H), 1.29 (s, 12H). |
16 g | With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 85℃; for 3h;Inert atmosphere; | 4-Bromobenzyl alcohol (15 g, 80.2 mmol), bis(pinacolato)diboron (30.6 g, 120.3 mmol), potassium acetate (23.6 g, 240 mmol) and Pd (PPh3)2Cl2 (5.6 g, 8 mmol) were added to 150 mL of dioxane, and the mixture was stirred at 85 C. for 3 hours under a nitrogen atmosphere. The reaction solution was filtered and concentrated under reduced pressure, and then extracted with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residues were purified by column chromatography (eluent: petroleum ether:ethyl acetate 60:1-10:1) to give 16 g of title product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | General procedure: Under a nitrogen atmosphere 0.075 g (0.2 mmol) of2,5-dibromo-3,4-dinitrothiophene were dissolved in 8 mLof anhydrous toluene and treated with 10 molpercent of the catalyst(catalysts I?IV). The mixture was then subjected toultrasound irradiation for 5 min and then stirred at roomtemperature for additional 25 min. Then, 0.5 mmol of theboronic acid, 1.6 mmol of potassium phosphate, and 2 mLof water were added, and the mixture was heated underreflux at 100°C for 48 h. After cooling to room temperature,the mixture was dried over magnesium sulfate andchromatographed (petroleum ether/dichloromethane 1:3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In water; at 150℃; for 0.333333h;Sealed tube; | Compound 1 (1 eq, 5.35 mmol), 4-(Trifluoromethyl)phenylboronic acid (1 eq, 5.35 mmol), TBAB (1 eq, 5.35 mmol), Na2C03 (3 eq, 16.05 mmol) were dissolved in 11 mL of water. Palladium acetate (0.4 % eq, 0.021 mmol) was then added and the reaction was stirred in a scelled tube and heated at 150C. After 20 min, the tube is slowly cooled down to rt and opened with caution. The biphase mixture is poured onto 10 mL of EtOAc and extracted (3 x 10 mL). The combined organic phases were dried and filtered. After removal of the solvent under reduced pressure, the remaining black oil was purified using column chromatography (silica gel, 80/20 Hex/EtOAc) to afford the desired compound (Rf = 0.2) as a colourless solid (1.29 g, 96%). 1H-NMR (CDC13, 600 MHz) delta 7.69 (s, 4H), 7.60 (d, J = 8.1Hz, 2H), 7.47 (d, J = 8.1Hz, 2H), 4.77 (s, 2H); 13C-NMR (CDCI3, 150 MHz) delta: 144.5, 141.1, 139.3, 129.1, 127.7, 127.6, 127.5, 125.9, 124.4, 65.1;ESI-MS m/z for C14HnF30 [MH]+, [MNa]+; |
Tags: 873-75-6 synthesis path| 873-75-6 SDS| 873-75-6 COA| 873-75-6 purity| 873-75-6 application| 873-75-6 NMR| 873-75-6 COA| 873-75-6 structure
A122781 [51760-22-6]
(5-Bromo-1,3-phenylene)dimethanol
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A136800 [68120-35-4]
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A122781 [51760-22-6]
(5-Bromo-1,3-phenylene)dimethanol
Similarity: 0.97
A136800 [68120-35-4]
(3-Bromo-4-methylphenyl)methanol
Similarity: 0.97
A122781 [51760-22-6]
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H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
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 |
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