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[ CAS No. 1037298-24-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1037298-24-0
Chemical Structure| 1037298-24-0
Chemical Structure| 1037298-24-0
Structure of 1037298-24-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1037298-24-0 ]

CAS No. :1037298-24-0 MDL No. :MFCD27978469
Formula : C6H5ClINO Boiling Point : -
Linear Structure Formula :- InChI Key :SHJLQMPWDJBRDG-UHFFFAOYSA-N
M.W : 269.47 Pubchem ID :92135481
Synonyms :

Calculated chemistry of [ 1037298-24-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.6
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.33
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 2.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.13 mg/ml ; 0.000484 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.464 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.251 mg/ml ; 0.000933 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.0

Safety of [ 1037298-24-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1037298-24-0 ]

* 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.

  • Downstream synthetic route of [ 1037298-24-0 ]

[ 1037298-24-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1037298-24-0 ]
  • [ 1629270-06-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C 3: methanol; sodium cyanoborohydride / toluene
Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C
  • 2
  • [ 1037298-24-0 ]
  • [ 1629270-07-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C 3: methanol; sodium cyanoborohydride / toluene 4: water; lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C
Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 60 °C
  • 3
  • [ 1037298-24-0 ]
  • [ 1629267-87-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C 3: methanol; sodium cyanoborohydride / toluene 4: water; lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 5: potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 60 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
  • 4
  • [ 1037298-24-0 ]
  • [ 1629267-96-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / methanol; toluene / 2 h / 20 °C 3.1: methanol; sodium cyanoborohydride / toluene 4.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 5.1: chloroformic acid ethyl ester; 4-methyl-morpholine / tetrahydrofuran / 0.75 h / -10 °C 5.2: 0.5 h / -10 - 20 °C
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2.1: acetic acid / toluene; methanol / 2 h / 20 °C 2.2: 15 h / 40 °C 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 60 °C 4.1: chloroformic acid ethyl ester; 4-methyl-morpholine / tetrahydrofuran / 0.75 h / -10 °C 4.2: 0.5 h / 20 °C
  • 5
  • [ 1037298-24-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran / 15 h / Inert atmosphere; Reflux 2: acetic acid / methanol; toluene / 2 h / 20 °C
  • 6
  • [ 1037298-24-0 ]
  • [ 23719-80-4 ]
  • [ 1629270-05-8 ]
YieldReaction ConditionsOperation in experiment
63% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In tetrahydrofuran for 15h; Inert atmosphere; Reflux; 44 2-Amino-5-chloro-4-cyclopropylphenol Example 44 2-Amino-5-chloro-4-cyclopropylphenol To a mixture of 2-amino-5-chloro-4-iodophenol (500 mg, 1.9 mmol), PdCl2(dppf) (136 mg, 0.19 mmol) in THF (10 mL) under argon at RT, cyclopropylmagnesium bromide (16 mL, 11.4 mmol, 0.7 M in THF) was added and the mixture was stirred at reflux for 15 h. The mixture was allowed to cool to RT, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (10-20% ethyl acetate/hexanes) to afford the desired product (220 mg, 63% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.27 (s, 1H), 6.62 (s, 1H), 6.22 (s, 1H), 4.53 (s, 2H), 1.89-1.93 (m, 1H), 0.83-0.87 (m, 2H), 0.46-0.49 (m, 2H).
63% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 15h; Inert atmosphere; Reflux; 56 2-Amino-S -chloro-4-cyclopropylphenol To a mixture of 2-amino-S-chloro-4-iodophenol (500 mg, 1.9 mmol), PdC12(dppf) (136 mg, 0.19 mmol) in THF (10 mL) under argon at RT, cyclopropylmagnesium bromide (16 mL, 11.4 mmol, 0.7 M in THF) was added and the mixture was stirred at reflux for 15 h. The mixture was allowed to cool to RT, and partitioned between ethyl acetate and water. The organic layer was washed with brine,dried over Na2504 and concentrated. The residue was purified by flash column chromatography on silica gel (10-20% ethyl acetate / hexanes) to afford the desired product (220 mg, 63% yield) as a brown solid. ‘H NMR (400 MHz, DMSO-d6) ö: 9.27 (s, 1H), 6.62 (s, 1H), 6.22 (s, 1H), 4.53(s, 2H), 1.89-1.93 (m, 1H), 0.83-0.87 (m, 2H), 0.46-0.49 (m, 2H).
  • 7
  • [ 6627-53-8 ]
  • [ 1037298-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trifluoromethanesulfonic acid anhydride; sulfuric acid; N-iodo-succinimide / 400 min / 20 °C 2: iron; ammonium chloride / ethanol; water; tetrahydrofuran / 2 h / 70 °C 3: boron tribromide / dichloromethane / 3 h / 20 °C / Cooling with ice
  • 8
  • [ 1508278-48-5 ]
  • [ 1037298-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: iron; ammonium chloride / ethanol; water; tetrahydrofuran / 2 h / 70 °C 2: boron tribromide / dichloromethane / 3 h / 20 °C / Cooling with ice
  • 9
  • [ 1508278-49-6 ]
  • [ 1037298-24-0 ]
YieldReaction ConditionsOperation in experiment
257 mg With boron tribromide In dichloromethane at 20℃; Cooling with ice; 2.3 (Step 3)
2-Amino-5-chloro-4-iodophenol
A solution of 4-chloro-5-iodo-2-methoxyaniline (400 mg) obtained in the preceding step 2 in dichloromethane (4.0 mL) was cooled in an ice bath, and boron tribromide (1 M solution in dichloromethane, 2.8 mL) was added thereto. The mixture was warmed to room temperature and stirred for 3 hours. Water and chloroform were added to the reaction mixture, and then, the mixture was neutralized with an aqueous sodium hydroxide solution, followed by extraction with chloroform/methanol (5/1). The organic layer was washed with water and saturated saline and dried over sodium sulfate, then the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (hexane:ethyl acetate) to obtain the title compound (257 mg) .
  • 10
  • [ 1011460-68-6 ]
  • [ 1037298-24-0 ]
  • [ 2648340-01-4 ]
YieldReaction ConditionsOperation in experiment
4 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 100℃; 57.1 (Step 1) 2-Amino-5-chloro-4-(1-(trifluoromethyl)vinyl)phenol To a solution of 2-amino-5-chloro-4-iodophenol (50 mg) obtained in Production Example 2 in 1,4-dioxane (1 mL), 4,4,6-trimethyl-2-(1-(trifluoromethyl)vinyl)-1,3,2-dioxaborinane (91.5 mg), Pd(PPh3)4 (32 mg), and a 2 M aqueous sodium carbonate solution (186 µL) were added, and the mixture was stirred overnight at 100°C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with saturated saline. The resultant product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to obtain the title compound (4.0 mg) .
4 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 100℃; 57.1 (Step 1) 2-Amino-5-chloro-4-(1-(trifluoromethyl)vinyl)phenol To a solution of 2-amino-5-chloro-4-iodophenol (50 mg) obtained in Production Example 2 in 1,4-dioxane (1 mL), 4,4,6-trimethyl-2-(1-(trifluoromethyl)vinyl)-1,3,2-dioxaborinane (91.5 mg), Pd(PPh3)4 (32 mg), and a 2 M aqueous sodium carbonate solution (186 µL) were added, and the mixture was stirred overnight at 100°C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with saturated saline. The resultant product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to obtain the title compound (4.0 mg) .
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