Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 5807-30-7 | MDL No. : | MFCD00004333 |
Formula : | C8H6Cl2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZOUPGSMSNQLUNW-UHFFFAOYSA-N |
M.W : | 205.04 | Pubchem ID : | 79874 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.01 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.36 cm/s |
Log Po/w (iLOGP) : | 1.72 |
Log Po/w (XLOGP3) : | 3.09 |
Log Po/w (WLOGP) : | 2.62 |
Log Po/w (MLOGP) : | 2.82 |
Log Po/w (SILICOS-IT) : | 2.83 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.3 |
Solubility : | 0.104 mg/ml ; 0.000506 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.54 |
Solubility : | 0.059 mg/ml ; 0.000288 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.41 |
Solubility : | 0.079 mg/ml ; 0.000385 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
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 |
---|---|---|
95% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5 h; | To an ice-cold solution of 2-(3,4-dichlorophenyl)acetic acid (19.36 g, 94.42 mmol) in THF (200 mL) was added portionwise 97percent LiAlH4 (5.54 g, 141.63 mmol). After the addition, the mixture was stirred at room temperature for 5 h. The resulting mixture was poured into ice-water (150 mL), and stirred for 0.5 h. The THF was removed under reduced pressure, then DCM (200 mL) was added. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/hexane = 1/5, V/V) to compound 6 as colourless oil (17.14 mg, 95percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | for 12 h; Heating / reflux | [0132] A solution of triphenylphosphine (11.90 g, 45.41 mmol) and imidazole (6.18 g, 90.82 mmol) in methylene chloride (80 mL) cooled to 0° C. was slowly treated with iodine (11.53 g, 45.41 mmol) followed by the dropwise addition of a solution of (tetrahydro-furan-2-yl)-methanol (4.0 mL, 41.28 mmol) in methylene chloride (5 mL). The resulting reaction mixture was allowed to warm to 25° C., where it was stirred for 4 h. The reaction mixture was then diluted with water (25 mL), and the reaction mixture was further extracted with methylene chloride (3.x.20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo at 25° C. The resulting solid was washed with pentane (4.x.50 mL) and filtered through a pad of silica gel. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 pentane/ether) afforded 2-iodomethyl-tetrahydro-furan (2.09 g, 25percent) as a clear, colorless liquid: EI-HRMS m/e calcd for C5H9IO (M+) 211.9698, found 211.9708. [0133] A solution of (3,4-dichloro-phenyl)-acetic acid (14.0 g, 0.07 mol) in methanol (71 mL) was treated with a catalytic amount of concentrated sulfuric acid. The reaction mixture was heated under reflux for 12 h. The reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded (3,4-dichloro-phenyl)-acetic acid methyl ester (15.0 g, quant.) as a white solid: mp 30-32° C.; EI-HRMS m/e calcd for C9H8Cl2O2 (M+) 217.9901, found 217.9907. [0134] A solution of diisopropylamine (0.59 mL, 4.51 mmol) in tetrahydrofuran (30 mL) was cooled to -78° C. under an argon atmosphere and then was treated with a 2.5M solution of n-butyllithium in hexanes (1.8 mL, 4.51 mmol). The reaction mixture was stirred at -78° C. for 15 min, after which time, a solution of (3,4-dichloro-phenyl)-acetic acid methyl ester (825 mg, 3.76 mmol) in tetrahydrofuran (3 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1 mL) was slowly added via a cannula. The bright yellow solution was allowed to stir at -78° C. for 1 h, after which time, a solution of 2-iodomethyl-tetrahydro-furan (798 mg, 3.76 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was added via a cannula. The reaction mixture was stirred at -78° C. for 1 h and then allowed to warm to 25° C., where it was stirred for 14 h. The reaction mixture was then quenched by the addition of a saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (3.x.20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester (501 mg, 44percent) as a colorless oil: EI-HRMS m/e calcd for C14H16Cl2O3 (M+) 302.0477, found 302.0464. [0135] A solution of 2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester (617 mg, 2.04 mmol), methylurea (302 mg, 4.07 mmol), and a solution of magnesium methoxide in methanol (7.4 wt. percent, 4.63 mL, 3.06 mmol) was heated at 100° C. for 8 h. After this time, the reaction mixture was concentrated in vacuo, dissolved in ethyl acetate (50 mL), and then filtered through a pad of silica gel. The organics were then concentrated in vacuo to give the crude product. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 1-[2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionyl]-3-methyl-urea as a white solid: EI-HRMS m/e calcd for C15H18Cl2N2O3 (M+) 344.0694, found 344.0699. |
98% | With sulfuric acid In 1,2-dichloro-ethane at 50℃; for 1.75 h; | REFERENCE SYNTHETIC EXAMPLE 1 Methyl 3,4-dichlorophenyl acetate Methanol (59 mL, 3.0 equivalent amounts) was added to a 1,2-dichloroethane (400 mL) solution of 3,4-dichlorophenyl acetic acid (100 g, 0.488 mol). The solution was heated to 50°C, and then concentrated sulfuric acid (10 mL) was dropwise added over a period of 15 minutes, followed by stirring at 50°C for 1.5 hours. The reaction solution was cooled to room temperature, followed by liquid separation to remove a sulfuric acid layer, and the obtained organic layer was sequentially washed with water, a saturated sodium hydrogencarbonate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to give the desired product as a colorless oil (105 g, yield: 98percent). 1H-NMR (300 MHz, ppm in CDCl3) δ:3.59 (s,2H), 3.71 (s,3H), 7.12(dd,J=8.4 Hz,1.8 Hz,1H), 7.38-7.41 (m,2H). |
98.58% | at 0 - 20℃; for 3 h; Inert atmosphere; Schlenk technique | General procedure: Thionyl chloride (1.06 mL, 14.63 mmol) was added to dropwise the solution of phenyl aceticacid derivatives (1 g, 4.877 mmol) in methanol (10 mL) at 0 . The reaction was allowed to room temperature for 3 h. The reaction mixture was evaporated under reduced pressure. The residue was dissolved ethyl acetate and water. The mixture was extracted with ethyl acetate and washed with sodium hydrogen carbonate aqueous solution. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6a-f. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With boric acid In 5,5-dimethyl-1,3-cyclohexadiene for 16 h; Reflux | General procedure: To a stirred solution of benzene-1,2-diamine 1 (1.85 mmol)in xylenes (10 mL) were added carboxylic acid 2 (2.77 mmol)and boric acid (0.185 mmol). The resulting solution wasrefluxed for 16 h. After cooling to room temperature, the reactionwas concentrated under reduced pressure and diluted withEtOAc (50 mL). The organic phase was washed with saturatedNaHCO3 solution (2 50 mL), dried over anhydrous Na2SO4and then concentrated under reduced pressure. The residuewas purified by silica gel flash column chromatography (elutingwith 10–15percent Ethyl acetate in hexanes) to afford the title compounds3a–y and 5.6.2.8 2-(3,4-Dichlorobenzyl)-1H-benzo[d]imidazole (3h) Yield 65percent; Off white solid; mp 189-191 °C; IR (KBr) 2851, 2758, 1508, 1451, 1410, 1241, 1183, 1027, 754 cm-1; 1H NMR (400 MHz, DMSO-d6) δ 12.30 (br s, 1H), 7.64 (d, J = 2.20 Hz, 1H), 7.59 (d, J = 8.05 Hz, 1H), 7.48-7.56 (m, 1H), 7.39-7.48 (m, 1H), 7.33 (dd, J = 2.19, 8.29 Hz, 1H), 7.08-7.18 (m, 2H), 4.21 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 152.7, 138.8, 131.0, 130.7, 129.5, 129.4, 121.5, 33.7; HRMS calcd for C14H10Cl2N2 m/z 276.0225, found 276.0221. |
[ 51719-65-4 ]
2-(3,5-Dichlorophenyl)acetic acid
Similarity: 0.91
[ 6725-44-6 ]
Methyl 2-(3,4-dichlorophenyl)acetate
Similarity: 0.89
[ 51719-65-4 ]
2-(3,5-Dichlorophenyl)acetic acid
Similarity: 0.91
[ 6725-44-6 ]
Methyl 2-(3,4-dichlorophenyl)acetate
Similarity: 0.89
[ 51719-65-4 ]
2-(3,5-Dichlorophenyl)acetic acid
Similarity: 0.91
[ 2019-34-3 ]
3-(4-Chlorophenyl)propanoic acid
Similarity: 0.88