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CAS No. : | 223576-64-5 | MDL No. : | MFCD18383028 |
Formula : | C8H6BClO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IODPQZJZPKMFKV-UHFFFAOYSA-N |
M.W : | 196.40 | Pubchem ID : | 18476279 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 51.05 |
TPSA : | 53.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.16 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.89 |
Log Po/w (WLOGP) : | 0.77 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 0.4 |
Consensus Log Po/w : | 0.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.69 |
Solubility : | 0.397 mg/ml ; 0.00202 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.64 |
Solubility : | 0.452 mg/ml ; 0.0023 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.8 |
Solubility : | 0.313 mg/ml ; 0.00159 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.71 |
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 |
---|---|---|
83% | Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; Dimethyl ether at -60 - -10℃; for 1.25 h; Stage #2: With Triisopropyl borate In hexane; Dimethyl ether at -60℃; Stage #3: With hydrogenchloride In hexane; Dimethyl ether; water for 1 h; |
5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent. [0323] To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA). The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise. It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate. After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h. The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively. The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether. All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification. [0324] yield: 9.4 g (83percent); MS 196 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With hydrogenchloride; n-butyllithium In PPA; hexane | Step A: 5-Chlorobenzofuran-2-boronic acid 5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent. To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA). The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise. It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate. After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h. The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively. The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether. All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification. yield: 9.4 g (83percent); MS 196 (M+). |
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