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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 51934-41-9 |
Formula : | C9H9IO2 |
M.W : | 276.07 |
SMILES Code : | O=C(OCC)C1=CC=C(I)C=C1 |
MDL No. : | MFCD00017344 |
InChI Key : | YCBJOQUNPLTBGG-UHFFFAOYSA-N |
Pubchem ID : | 142891 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 55.25 |
TPSA ? Topological Polar Surface Area: Calculated from | 26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.6 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 3.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 3.11 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.99 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 2.89 |
Log S (ESOL):? ESOL: Topological method implemented from | -3.8 |
Solubility | 0.0441 mg/ml ; 0.00016 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -3.52 |
Solubility | 0.0838 mg/ml ; 0.000304 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.83 |
Solubility | 0.0411 mg/ml ; 0.000149 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 | -5.65 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 | 0.0 |
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 | 1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.91 |
* 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 |
---|---|---|
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;palladium diacetate; In 1,4-dioxane;Sonographic reaction; Inert atmosphere; | A mixture of 5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), BINAP (0.1 eq), 4-Iodo-benzoic acid ethyl ester (1.5 eq) and 1,4-dioxane was sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1200C or in a flasked equipped with a cooling system for 16 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The product was used in the next step without futher purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.9% | With potassium carbonate;palladium on carbon; In ethanol; water; toluene; for 2h;Reflux; Inert atmosphere; | Ethyl 4-iodoethylbenzoate (1) (25.0 g), <strong>[212386-71-5]4-ethoxy-2,3-difluorophenylboronic acid</strong> (2) (20.1 g), potassium carbonate (25.0 g), Pd/C (0.25 g), toluene (100 ml), ethanol (100 ml) and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25 C, and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases. The extraction to an organic phase was carried out. The organic phase obtained was washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel; toluene). The product was further purified by means of recrystallization from ethanol and dried, giving 18.8 g of ethyl 4-ethoxy-2,3-difluoro-4'-biphenylcarboxylate (3). The yield based on the compound (1) was 67.9%. |
67.9% | With potassium carbonate;5% Pd(II)/C(eggshell); In ethanol; water; toluene; for 2h;Inert atmosphere; Reflux; | Example 1; Synthesis of 4-ethoxy-2,3-difluoro-4'-[2,3-difluoro-4-(4-pentylcyclohexyl)phenoxymethyl]-1,1'-biphenyl (No. 1123) [Show Image] First Step: 4-Iodoethyl benzoate (1) (25.0 g), <strong>[212386-71-5]4-ethoxy-2,3-difluorophenylboronic acid</strong> (2) (20.1 g), potassium carbonate (25.0 g), palladium on carbon (NX type of 5%Pd/C; 50% wet; made by N. E. Chemcat; hereinafter referred to as Pd/C) (0.25 g), toluene (100 ml), ethanol (100 ml) and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25 C, and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The product was further purified by means of recrystallization from ethanol and dried, giving 18.8 g of ethyl 4-ethoxy-2,3-difluoro-4'-biphenylbenzoate (3). The yield based on the compound (1) was 67.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With silver(I) acetate; palladium diacetate; acetic acid; at 50℃; for 12h; | General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium acetate; palladium diacetate; In dimethyl sulfoxide; at 120℃; for 24h;Schlenk technique; | General procedure: A mixture of benzoyl aminoacetic acid 1a (90 mg, 0.5 mmol), 4-iodo-toluene 2a (218 mg, 1.0 mmol), Pd(OAc)2(11 mg, 0.05 mmol), anhydrous NaOAc (82 mg, 1.0 mmol), and DMSO (2 mL) wasplaced in a 25 mL Schlenk tube with a rubber plug in air. The tube was heatedat 120 for 24 h. The reaction mixture was cooled, diluted with alcohol, filtered through Celite, and concentrated in vacuo. Theresidue was purified by silica gel column chromatographywith ethyl acetate/ acetic acid (v:v = 80:1) to afford the desired product 3a (120 mg, 89percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 115℃; for 16h;Inert atmosphere; | General procedure: Compound 4 (5.0g, 18mmol) was dissolved in 96 toluene (100mL), followed by the addition of 97 piperidin-2-one (3.6g, 36mmol), anhydrous 98 potassium phosphate (7.8g, 36mmol), 99 CuI (0.34g, 1.8mmol) and 100 N,N′-dimethylethanediamine (0.39mL, 3.6mmol). The mixture was degassed and refilled with N2 three times and was heated to 115C under N2 for 16h, cooled, and quenched with water (100mL). The organics were extracted with ethyl acetate (2×75mL) and dried with Na2SO4. Purification by silica gel column chromatography (n-hexane/ethyl acetate, 6/1-2/1, as eluent) afforded compound 101 5a as off-white solid (3.5g, 65%). |
Tags: 51934-41-9 synthesis path| 51934-41-9 SDS| 51934-41-9 COA| 51934-41-9 purity| 51934-41-9 application| 51934-41-9 NMR| 51934-41-9 COA| 51934-41-9 structure
A202441 [103440-53-5]
Methyl 4-iodo-2-methylbenzoate
Similarity: 0.94
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