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CAS No. : | 164650-68-4 | MDL No. : | MFCD08234653 |
Formula : | C8H7ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BMSBBELFYSUAOR-UHFFFAOYSA-N |
M.W : | 170.59 | Pubchem ID : | 21904633 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.33 |
TPSA : | 26.3 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) : | -5.47 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 2.63 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 1.71 |
Log Po/w (SILICOS-IT) : | 2.61 |
Consensus Log Po/w : | 2.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.83 |
Solubility : | 0.255 mg/ml ; 0.00149 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.83 |
Solubility : | 0.251 mg/ml ; 0.00147 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.08 |
Solubility : | 0.141 mg/ml ; 0.000824 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
25% | Stage #1: With boron tribromide In dichloromethane at 0℃; for 1.25 h; Stage #2: With water In dichloromethane |
A solution of 3-chloro-5-methoxybenzaldehyde (22.8 g, 134 mmol; see step (i) above) in [CH2CL2] (250 mL) was cooled to [0°C.] Boron tribromide (15.8 mL, 167 mmol) was added dropwise over 15 min. After stirring, the reaction mixture for 2 h, H20 (50 mL) was added slowly. The solution was then extracted with [ET2O] (2 x 100 mL). The organic layers were combined, dried [(NA2S04),] filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub-title compound (5.2 g, 25percent). 'H NMR (300 MHz, CDCl3) 8 9.85 (s, 1H), 7.35 (s, lH), 7.20 (s, lH), 7.10 (s, [LH),] 3.68 (s, [LH)] |
25% | Stage #1: With boron tribromide In dichloromethane at 0℃; for 2.25 h; Stage #2: With water In dichloromethane |
A solution of 3-chloro-5-methoxybenzaldehyde (22.8 g, 134 mmol; see step (i) above) in CH2Cl2 (250 mL) was cooled to 0° C. Boron tribromide (15.8 mL, 167 mmol) was added dropwise over 15 min. After stirring, the reaction mixture for 2 h, H2O (50 mL) was added slowly. The solution was then extracted with Et2O (2*100 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluding with Hex:EtOAc (4:1) afforded the sub-title compound (5.2 g, 25percent). 1H NMR (300 MHz, CDCl3) δ9.85 (s, 1H), 7.35 (s,1H), 7.20 (s, 1H), 7.10 (s,1H), 3.68 (s,1H) |
25% | With boron tribromide In dichloromethane at 0℃; for 2.25 h; | A solution of 3-chloro-5-methoxybenzaldehyde (22. 8 g, 134 mmol; see step (i) above) in CH2C12 (250 mL) was cooled to [0°C.] Boron tribromide (15. [8] mL, 167 mmol) was added dropwise over 15 min. After stirring, the reaction mixture for 2 h, [HA0] (50 mL) was added slowly. The solution was then extracted with Et20 (2 x 100 mL). The organic layers were combined, dried [(NA2S04),] filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub-title compound (5.2 g, [25percent).] |
25% | With boron tribromide In dichloromethane at 0℃; for 2.25 h; | A solution of [3-CHLORO-5-METHOXYBENZALDEHYDE] (22.8 g, 134 mmol; see step (i) above) in [CH2C12] (250 mL) was cooled to [0°C.] Boron [TRIBROMIDE] (15.8 mL, 167 mmol) was added dropwise over 15 min. After stirring, the reaction mixture for 2 h, [H20] (50 mL) was added slowly. The solution was then extracted with [ET20] (2 x 100 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub-title compound (5.2 g, 25percent). 'H NMR (300 MHz, CDCl3) 8 9.85 (s, [1H),] 7.35 (s, [LH),] 7.20 (s, [LH),] 7.10 (s, [LH),] 3.68 (s, [1 H)] |
25% | With boron tribromide In dichloromethane at 0℃; for 2.25 h; | [(II)] 3-Chloro-5-hydroxybenzaldehyde A solution of 3-chloro-5-methoxybenzaldehyde (22.8 g, 134 mmol; see step (i) above) in [CH2CI2] (250 mL) was cooled to [0°C.] Boron tribromide (15.8 mL, 167 mmol) was added dropwise over 15 min. After stirring, the reaction mixture for 2 h, H20 (50 mL) was added slowly. The solution was then extracted with Et20 (2 x 100 mL). The organic layers were combined, dried [(NA2SO4),] filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub-title compound (5.2 g, 25percent). 'H NMR (300 MHz, [CDC13)] 8 9.85 (s, 1H), 7.35 (s, lH), 7.20 (s, [LH),] 7.10 (s, lH), 3.68 (s, [1 H)] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: With magnesium; ethylene dibromide In tetrahydrofuran at 0 - 25℃; for 3 h; Heating / reflux Stage #3: With hydrogenchloride; water In tetrahydrofuran |
3,5-Dichloroanisole (74.0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N HCl) in THF (100 mL) at 25° C. After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to 0° C., and N,N-dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3*400 mL) and 6N HCl (500 mL). The combined organic extracts were washed with brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography (2*) on silica gel eluding with Hex:EtOAc (4:1) afforded the sub-title compound (38.9 g, 54percent/) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ9.90 (s, 1H), 7.53 (s, 1H), 7.38 (s, 1H), 7.15 (s, 1H), 3.87 (s, 3H). |
54% | Stage #1: With magnesium; ethylene dibromide In tetrahydrofuran for 3 h; Heating / reflux Stage #2: at 0℃; |
3,5-Dichloroanisole (74.0 g, 419 mmol) in THF (200 [ML)] was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N [HC1)] in THF (100 [ML)] at [25°C.] After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to [0°C,] and [N, N-DIMETHYLFORMAMIDE] (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3 x 400 mL) and 6N HCl (500 mL). The combined organic extracts were washed with brine (300 mL), dried [(NA2S04),] filtered and concentrated in vacuo to give an oil. Flash chromatography (2x) on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub- title compound (38.9 g, 54percent) as a yellow oil. [APOS;H] NMR (300 MHz, [CDC13)] [8] 9.90 (s, 1H), 7.53 (s, 1H), 7.38 (s, 1H), 7.15 (s, 1H), 3.87 (s, 3H). |
54% | Stage #1: With magnesium; ethylene dibromide In tetrahydrofuran for 3 h; Heating / reflux Stage #2: at 0℃; |
[5-DICHLOROANISOLE] (74.0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N HC1) in THF (100 mL) at [25°C.] After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to [0°C,] and N, N-dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3 x 400 mL) and 6N HCI (500 mL). The combined organic extracts were washed with brine (300 [ML),] dried [(NA2SO4),] filtered and concentrated in vacuo to give an oil. Flash chromatography (2x) on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub- title compound (38.9 g, 54percent) as a yellow oil. 'H NMR (300 MHz, [CDC13)] 8 9.90 (s, 1H), 7.53 (s, 1H), 7.38 (s, 1H), 7.15 (s, 1H), 3.87 (s, 3H). |
54% | Stage #1: With magnesium; ethylene dibromide In tetrahydrofuran for 3 h; Heating / reflux Stage #2: at 0℃; |
3, [5-DICHLOROANISOLE] (74.0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N HCI) in THF (100 mL) at [25°C.] After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to [0°C,] and N, N-dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3 x 400 mL) and 6N HCI (500 mL). The combined organic extracts were washed with brine (300 mL), dried [(NA2SO4),] filtered and concentrated in vacuo to give an oil. Flash chromatography (2x) on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub-title compound (38.9 g, 54percent) as a yellow oil. 'H NMR (300 MHz, [CDCI3)] A 9.90 (s, 1H), 7.53 (s, 1H), 7.38 (s, 1H), 7.15 (s, 1H), 3.87 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | for 1.25 h; | [00325] A mixture of 3-chloro-5-methoxybenzyl alcohol (5.0g, 28.9 mmol) and pyridiniurn chlorochromate (20percent on alumina, 4Og, 37.8 mmol) was allowed to stir for 1.25 hr. Diethyl ether (200ml) was then added followed by filtration of precipitate. The filtrate was concentrated under reduced pressure and the resulting residue was purified via silica gel chromatography using 40percent dichloromethane, 60percent petroleum ether as eluant, to give 3.8g of 3-chloro-5-methoxybenzaldehyde (78percent). 1H-NMR (CDCl3): 3.84 (s, 3H) 7.13 (s, IH), 7.28 (s, IH), 7.41 (S5 IH), 9.89 (s, IH). |
78% | With pyridinium chlorochromate In diethyl ether | Preparation of 3-chloro-5-methoxybenzaldehyde A mixture of 3-chloro-5-methoxybenzyl alcohol (5.0 g, 28.9 mmol) and pyridinium chlorochromate (20percent on alumina, 40 g, 37.8 mmol) was allowed to stir for 1.25 hr. Diethyl ether (200 ml) was then added followed by filtration of precipitate. The filtrate was concentrated under reduced pressure and the resulting residue was purified via silica gel chromatography using 40percent dichloromethane, 60percent petroleum ether as eluant, to give 3.8 g of 3-chloro-5-methoxybenzaldehyde (78percent). 1H-NMR (CDCl3): 3.84 (s, 3H) 7.13 (s, 1H), 7.28 (s, 1H), 7.41 (s, 1H), 9.89 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: With magnesium In tetrahydrofuran for 3 h; Heating / reflux Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; |
3,5-Dichloroanisole [(74.] 0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N [HCL)] in THF (100 [ML)] at [25°C.] After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to [0°C,] and [N, N-] dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3 x 400 mL) and 6N HCl (500 mL). The combined organic extracts were washed with brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography (2x) on silica gel eluting with Hex: EtOAc (4: 1) afforded the sub-title compound [(38.] 9 g, 54percent) as a yellow oil. [APOS;H] NMR (300 MHz, [CDCL3)] 8 9.90 (s, 1H), 7.53 (s, 1H), 7.38 (s, 1H), 7.15 (s, [1H),] 3.87 (s, 3H). |
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