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[ CAS No. 164650-68-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 164650-68-4
Chemical Structure| 164650-68-4
Chemical Structure| 164650-68-4
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Product Details of [ 164650-68-4 ]

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 :

Calculated chemistry of [ 164650-68-4 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 164650-68-4 ]

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:

Application In Synthesis of [ 164650-68-4 ]

* 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.

  • Upstream synthesis route of [ 164650-68-4 ]
  • Downstream synthetic route of [ 164650-68-4 ]

[ 164650-68-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 164650-68-4 ]
  • [ 1829-33-0 ]
YieldReaction ConditionsOperation 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)]

Reference: [1] Patent: WO2003/101957, 2003, A1, . Location in patent: Page 29-30
[2] Patent: US2004/19033, 2004, A1, . Location in patent: Page/Page column 16
[3] Patent: WO2003/101423, 2003, A1, . Location in patent: Page 19-20
[4] Patent: WO2003/101424, 2003, A1, . Location in patent: Page 21-22
[5] Patent: WO2003/101956, 2003, A1, . Location in patent: Page 40
  • 2
  • [ 33719-74-3 ]
  • [ 68-12-2 ]
  • [ 164650-68-4 ]
YieldReaction ConditionsOperation 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).

Reference: [1] Patent: US2004/19033, 2004, A1, . Location in patent: Page/Page column 16
[2] Patent: WO2003/101423, 2003, A1, . Location in patent: Page 19
[3] Patent: WO2003/101424, 2003, A1, . Location in patent: Page 21
[4] Patent: WO2003/101956, 2003, A1, . Location in patent: Page 39; 40
  • 3
  • [ 82477-68-7 ]
  • [ 164650-68-4 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Patent: WO2007/25307, 2007, A2, . Location in patent: Page/Page column 306
[2] Patent: US2010/272681, 2010, A1,
[3] Patent: WO2008/106139, 2008, A1, . Location in patent: Page/Page column 475-476
  • 4
  • [ 33719-74-3 ]
  • [ 106-93-4 ]
  • [ 164650-68-4 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Patent: WO2003/101957, 2003, A1, . Location in patent: Page 29
  • 5
  • [ 33719-74-3 ]
  • [ 164650-68-4 ]
Reference: [1] Patent: US6255301, 2001, B1,
  • 6
  • [ 1984-59-4 ]
  • [ 106-93-4 ]
  • [ 164650-68-4 ]
Reference: [1] Patent: US2009/155168, 2009, A1,
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