Structure of 1-(Benzyloxy)-4-bromobenzene
CAS No.: 6793-92-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su ;
Abstract: In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
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Purchased from AmBeed: 20469-65-2 ; 13675-18-8 ; 2564-83-2 ; 872-31-1 ; 192863-35-7 ; 871231-46-8 ; 192863-36-8 ; 6793-92-6 ; 3972-65-4 ; 2398-37-0 ; 850623-47-1 ; 929626-22-2 ; 705254-31-5 ; 580-13-2 ; 2635-13-4 ; 623-12-1 ; 1015082-71-9 ; 52415-29-9 ; 23145-07-5 ; 619-42-1 ; 99-90-1 ; 192863-37-9 ; 578-57-4 ; 407-14-7 ; 216434-82-1 ; 668984-08-5 ; 423118-47-2 ; 108-85-0 ; 252726-24-2 ; 101-55-3 ; 850623-36-8 ; 4923-87-9 ; 1394827-04-3 ; 850623-42-6 ; 438553-44-7 ; 460-00-4 ; 1187951-62-7 ; 705254-34-8 ; 111-83-1 ; 111-83-1 ; 906007-40-7 ; 1443282-44-7 ; 1000160-76-8 ; 1111733-01-7 ; 99-90-1
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CAS No. : | 6793-92-6 |
Formula : | C13H11BrO |
M.W : | 263.13 |
SMILES Code : | C1=C(C=CC=C1)COC2=CC=C(C=C2)Br |
MDL No. : | MFCD00028016 |
InChI Key : | OUQSGILAXUXMGI-UHFFFAOYSA-N |
Pubchem ID : | 138835 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.08 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 65.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.94 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.48 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.01 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.07 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.69 |
Solubility | 0.0054 mg/ml ; 0.0000205 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.39 |
Solubility | 0.0106 mg/ml ; 0.0000404 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.91 |
Solubility | 0.000321 mg/ml ; 0.00000122 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
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 |
-4.72 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 |
1.0 |
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) |
1.65 |
* 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 |
---|---|---|
75% | Step 1 ; 3-(4-Benzyloxy-benzoyl)-azetidine-1-carboxylic aoid tert-butyl esterTo a stirred solution of 1-(Benzyloxy)-4-bromobenzene (32.3 g, 0.12 mol) in dry THF (250 mL) was added n-Butyl lithium (83 mL. 0.13 mol. 1.6 M solution in hexane) in drops at -78 C under nitrogen and the reaction mixture was stirred at same temperature for 1 nr. To this reaction mixture, a solution of fert-butyl 3- [methoxy(methyl)amlno]carbonyl}azetidine-1-carboxylate (25 g, 0.10 mol) in dry THF (150 mL) was added in drops. The reaction mixture was stirred at -78 C for 1 nr. After completion of reaction, the reaction mixture was quenched with ice water and extracted with ethyl acetate (2 x 200 mL). The combined organic layer washed with water (200 mL), brine (100 mL) and dried over sodium sulphate. The solvent was concentrated under reduced pressure; the crude product was slurred with pet ether (100 mL) and ethyl acetate (50 mL). The solids were filtered to afford (30g, 75 %) of the titled compound as white solid. TLC-Pet ether/ Ethyl acetate (8:2), R, = 0.7; 'H NMR (400MHz, DMSO-de) δ 7.84-7.82 (t. J = 8.0 Hz, 2H). 7.46-7.31 (m, 5H), 7.14-7.10 (m, 2H), 5.20 (s, 2H), 4.35-4.28 (m, 1H), 4.10 (s, 2H), 3.93 (s, 2H). 1.36 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 110℃; for 20h;Inert atmosphere; | To the round-bottom flask 1 - (benzyloxy) - 4-bromobenzene (2.00g, 7 . 60mmol), <strong>[109-11-5]morpholine-3-one</strong> (1.15g, 11 . 37mmol), cuprous iodide (290 mg, 1 . 52mmol), N, N '-dimethyl-ethylenediamine (0.4 ml, 4 . 00mmol), potassium carbonate (2.11g, 15 . 3mmol) and toluene (20 ml)is added, under nitrogen and heated to 110 C stirring 20 hours. Cooling to room temperature, add saturated ammonium chloride solution (20 ml) quenching the reaction, ethyl acetate (50 ml × 3) extraction. Combined with the phase, saturated salt water (50 ml) to wash, dry anhydrous sodium sulfate. Filtering, distilling off the solvent under reduced pressure, the crude product purification column chromatography (petroleum ether/ethyl acetate (v/v)=1/2), get white solid (1.81g, 84.0%). |
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