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[ CAS No. 179898-50-1 ] {[proInfo.proName]}

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Chemical Structure| 179898-50-1
Chemical Structure| 179898-50-1
Structure of 179898-50-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 179898-50-1 ]

CAS No. :179898-50-1 MDL No. :MFCD08277278
Formula : C7H8BClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VHQABGUEHFRBRI-UHFFFAOYSA-N
M.W : 186.40 Pubchem ID :15766875
Synonyms :

Calculated chemistry of [ 179898-50-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.77
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 0.03
Log Po/w (MLOGP) : 0.6
Log Po/w (SILICOS-IT) : -0.1
Consensus Log Po/w : 0.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.37 mg/ml ; 0.00734 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.56 mg/ml ; 0.00834 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.03
Solubility : 1.73 mg/ml ; 0.00927 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 179898-50-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 179898-50-1 ]

* 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 [ 179898-50-1 ]
  • Downstream synthetic route of [ 179898-50-1 ]

[ 179898-50-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 174913-10-1 ]
  • [ 5419-55-6 ]
  • [ 179898-50-1 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With tert.-butyl lithium In tetrahydrofuran at -78 - 20℃; for 1 h;
Stage #2: for 3 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1.5 h;
1-Bromo-3-chloro-2-methoxybenzene(113.2 g, 426.4 mmol) was dissolved in tetrahydrofuran (1000 mL), the temperature was lowered to -78 ° C, and 1.7 M tert-butyllithium (t-BuLi) (251.7 mL, 426.4 mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropyl borate (B (OiPr) 3) (113.2 mL, 852.4 mmol) was added and stirred for 3 hours while gradually warming to room temperature. To the reaction mixture was added a 2 N aqueous hydrochloric acid solution (800 mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether, and vacuum dried. After drying, the product was recrystallized from chloroform and ethyl acetate and dried to obtain (3-chloro-2-methoxyphenyl) boronic acid (89.6 g, yield 91percent; MS: [M + H] + = 230).
Reference: [1] Patent: KR2018/10165, 2018, A, . Location in patent: Paragraph 0207-0210
  • 2
  • [ 174913-10-1 ]
  • [ 5419-55-6 ]
  • [ 7732-18-5 ]
  • [ 179898-50-1 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃; for 3 h;
Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; for 1.5 h;
1-Bromo-3-chloro-2-methoxybenzene (113.2 g, 426.4 mmol)The mixture was dissolved in tetrahydrofuran (1000 mL), the temperature was lowered to -78 ° C, and 1.7 M tert-butyllithium (t-BuLi) (251.7 mL, 426.4 mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropyl borate (B (OiPr) 3) (113.2 mL, 852.4 mmol) was added and stirred for 3 hours while slowly warming to room temperature. To the reaction mixture was added a 2 N aqueous hydrochloric acid solution (800 mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether, and vacuum dried. After drying, recrystallization from chloroform and ethyl acetate and drying afforded (3-chloro-2-methoxyphenyl) boronic acid (89.6 g, yield 91percent;
Reference: [1] Patent: KR2018/10166, 2018, A, . Location in patent: Paragraph 0203; 0204; 0205
  • 3
  • [ 174913-10-1 ]
  • [ 121-43-7 ]
  • [ 179898-50-1 ]
YieldReaction ConditionsOperation in experiment
91% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid EXAMPLE 217
7-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl)
3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91percent) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.
91% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid 3-Chloro-2-methoxyphenylboronic Acid (Structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91percent) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.
91% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid EXAMPLE 217
7-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl)
3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91percent) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.
91% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid EXAMPLE 217
7-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl)
3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H).
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91percent) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.

Reference: [1] Patent: US5688808, 1997, A,
[2] Patent: US5693646, 1997, A,
[3] Patent: US5693647, 1997, A,
[4] Patent: US5696127, 1997, A,
[5] Patent: US5688810, 1997, A,
  • 4
  • [ 174913-10-1 ]
  • [ 121-43-7 ]
  • [ 6942-36-5 ]
  • [ 89694-48-4 ]
  • [ 179898-50-1 ]
  • [ 179898-51-2 ]
YieldReaction ConditionsOperation in experiment
35% With n-butyllithium In methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate; (5-fluoro-2-methoxyphenyl)boronic acid EXAMPLE 217
7-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl)
3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H).
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91percent) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.
Methyl (3'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate).
This compound was prepared in a manner similar to that of methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate) (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (0.58 g, 2.2 mmol), (PPh3)4 Pd (77 mg, 0.066 mmol), and 5-chloro-2-methoxyphenylboronic acid (0.54 g, 2.9 mmol) to afford 245 mg (35percent) of methyl (3'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate) as a clear oil.
35% With n-butyllithium In methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate; (5-fluoro-2-methoxyphenyl)boronic acid EXAMPLE 217
7-Chloro-1,2-dihydro-2,2,4-trimethl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl) 3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 H).
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91percent) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.
Methyl (3'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate).
This compound was prepared in a manner similar to that of methyl (5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate) (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (0.58 g, 2.2 mmol), (PPh3)4 Pd (77 mg, 0.066 mmol), and 5-chloro-2-methoxyphenylboronic acid (0.54 g, 2.9 mmol) to afford 245 mg (35percent) of methyl (3'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate) as a clear oil.
Reference: [1] Patent: US5696130, 1997, A,
[2] Patent: US5696133, 1997, A,
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