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CAS No. : | 637-87-6 | MDL No. : | MFCD00001053 |
Formula : | C6H4ClI | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GWQSENYKCGJTRI-UHFFFAOYSA-N |
M.W : | 238.45 | Pubchem ID : | 12510 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.17 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.18 cm/s |
Log Po/w (iLOGP) : | 2.23 |
Log Po/w (XLOGP3) : | 3.62 |
Log Po/w (WLOGP) : | 2.94 |
Log Po/w (MLOGP) : | 3.79 |
Log Po/w (SILICOS-IT) : | 3.51 |
Consensus Log Po/w : | 3.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.15 |
Solubility : | 0.0167 mg/ml ; 0.0000701 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.31 |
Solubility : | 0.117 mg/ml ; 0.000492 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.97 |
Solubility : | 0.0256 mg/ml ; 0.000107 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.08 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302+H312+H332 | 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 bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1 h; | General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65°C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 50℃; for 7 h; Stage #2: With sodium tetrahydroborate In DMF (N,N-dimethyl-formamide) at 5℃; for 0.5 h; |
EXAMPLE 1Pd Coupling Reaction and Reduction of Aldehyde 95.38 g (400 mmol) of p-chloroiodobenzene, 34.85 g (600 mmol) of ally alcohol, 0.089 g (0.4 mmol) of palladium acetate and 47.99 g (2,000 mmol) of sodium hydrogencarbonate, were added to 200 ml of dimethylformamide (DMF), followed by heating until the internal temperature of the suspension became 50° C. The heating was continued for 7 hours, and after confirming the formation of the aldehyde compound by gas chromatogram, the suspension was cooled to 5° C. Then, 4.54 g (120 mmol) of sodium borohydride was added, followed by stirring for 30 minutes. Then, 100 ml of a saturated ammonium chloride aqueous solution, 100 ml of water and 200 ml of toluene were added, followed by stirring for one hour. After removing insolubles by Celite filtration, liquid separation was carried out, and the water layer was extracted again with 200 ml of toluene. The tolune layers were put together, concentrated and then distilled (107° C./1 mmHg) to obtain 63.4 g (y 93percent) of 3-(p-chlorophenyl)-1-propanol {compound (1)} as a colorless oily substance. From the analysis by gas chromatography, this product was found to contain 6percent of the branched isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: With copper(l) iodide; caesium carbonate In tetrahydrofuran at 20℃; for 0.0833333 h; Inert atmosphere Stage #2: at 35℃; Inert atmosphere |
a) (4-Chloro-phenyl)-propynoic acid ethyl ester (Va) Under argon atmosphere, a four neck flask was charged with 1-chloro-4-iodo-benzene (130.0 g, 0.55 mol), bis(triphenylphosphine) palladium(II) chloride (7.57 g, 10.8 mmol, 2 mol percent), copper(I) iodide (4.19 g, 22.0 mmol, 4 mol percent) and dry THF (1.4 l). At r.t., cesium carbonate (355.3 g, 1.09 mol, 2 eq.) was added over 5 min. Afterwards propynoic acid ethyl ester (111.3 ml, 1.09 mol, 2 eq.) was added, and the reaction mixture was stirred overnight at 35° C. An additional portion of propynoic acid ethyl ester (11.1 ml, 0.11 mol, 0.2 eq.) was added, and the reaction was stirred for another 3 h at 35° C. The reaction mixture was evaporated to dryness, and the residue was taken up in toluene (0.5 l) and heptane (1 l). The resulting suspension was stirred at 40° C. for 1 h and filtered over celite. The filtrate was concentrated, and the product purified by silica gel filtration (toluene/heptane 1:2) to yield 72.6 g (61percent) of Va as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With copper In dimethyl sulfoxide at 80℃; for 20 h; | To a stirred solutIon of I-chioro-4-iodobenzene (15.0 g, 63 mmo) and ethyl 2-bromo- 2,2—ditluoroacetate (12.8g. 63 mmo1 in DMS() (300 mL) was added Cu powder (8.0g. 126 nimol). i’he mixture was heated to 80 °C, and stirred for 20 hrs. The mixture was cooled to it, and poured into an aqueous solution of K2HPO4.3N20 (1 1.0 g) in water (1.5 L) under sdrring After stirring for 30 mm at rt, the mixture was filtered through a pad of celite. The filter cake was extracted with ether.The conibned organic phases were washed with waler and brine, dried over Na2SO4 and concentrated, The concentrate was purified column chromatography over silica gel (eluent: hexane) to afford the title compound as a colorless oil (6.8 g, 46percent). K NMR. (400 MHz, CDCI3) 67.55 jd, ,J 8.4 Hz, 211), 7.44 (d, .1 8.4 Hz, 2K), 4.30 (q, J 7.1 Hz,2H), 1.31 (t,J7.l Hz,3H). |