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[ CAS No. 1261675-06-2 ] {[proInfo.proName]}

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Chemical Structure| 1261675-06-2
Chemical Structure| 1261675-06-2
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Product Details of [ 1261675-06-2 ]

CAS No. :1261675-06-2 MDL No. :MFCD18391952
Formula : C10H11BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BPPNXHOUQPFBCW-UHFFFAOYSA-N
M.W : 259.10 Pubchem ID :75355402
Synonyms :

Calculated chemistry of [ 1261675-06-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.99
TPSA : 46.53 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 2.47
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 2.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.275 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.286 mg/ml ; 0.00111 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.56
Solubility : 0.0707 mg/ml ; 0.000273 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.67

Safety of [ 1261675-06-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1261675-06-2 ]

* 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 [ 1261675-06-2 ]

[ 1261675-06-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 139102-34-4 ]
  • [ 1261675-06-2 ]
  • 2
  • [ 17102-63-5 ]
  • [ 1261675-06-2 ]
  • 3
  • [ 43192-33-2 ]
  • [ 1261675-06-2 ]
  • 4
  • [ 1528736-48-2 ]
  • [ 1261675-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen; 5% rhodium on activated aluminium oxide / methanol / 3 h / 1034.32 Torr 2: potassium hydroxide / methanol / 60 °C / Inert atmosphere
  • 5
  • [ 1261653-54-6 ]
  • [ 1261675-06-2 ]
YieldReaction ConditionsOperation in experiment
86% With potassium hydroxide In methanol at 60℃; Inert atmosphere; 5.2.17 3-(4-Bromo-2-methoxyphenyl)propionic acid (34b) General procedure: Methyl 3-(4-bromo-2-methoxyphenyl)propionate (1.38g, 5.1mmol) was dissolved in a 1.0M solution of KOH in MeOH (25mL, 25mmol, 5equiv), and the combined solution was heated at 60°C overnight. The solvent was evaporated, and the resulting solid was dissolved in water (15mL). The aqueous solution was washed with CHCl3 (2×20mL), and the pH of the aqueous portion was adjusted to 3 with 3M aqueous HCl. The precipitate that formed was filtered and washed with water. The solid was dissolved in diethyl ether and the solution was dried (MgSO4), filtered, and evaporated to give 1.12g (86%) of product as a white powder: Rf 0.31 (25% EtOAc/hexane; mp 112°C (subl.); 1H NMR (DMSO-d6) δ 12.1 (b, 1H), 6.9-6.83 (m, 3H), 3.58 (s, 3H), 2.51 (t, 2H), 2.22 (t, 2H).
  • 6
  • [ 1261675-06-2 ]
  • [ 1528736-51-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; triphenylphosphine; sodium carbonate / water; isopropyl alcohol / 4 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 2 h / Inert atmosphere
  • 7
  • [ 1261675-06-2 ]
  • [ 1528736-50-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; triphenylphosphine; sodium carbonate / water; isopropyl alcohol / 4 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere
  • 8
  • [ 1261675-06-2 ]
  • [ 329214-79-1 ]
  • [ 1528736-49-3 ]
YieldReaction ConditionsOperation in experiment
34% With palladium diacetate; sodium carbonate; triphenylphosphine In water; isopropyl alcohol at 80℃; for 4h; Inert atmosphere; 5.2.18 3-(2-Methoxy-4-(pyridin-3-yl)phenyl)propionic acid (36) A mixture of 3-(4-bromo-2-methoxyphenyl)propionic acid (34; 520mg, 2.0mmol), pyridine-3-boronic acid pinacol ester (470mg, 2.11mmol, 1.05equiv), palladium acetate (14mg, 0.06mmol, 3%), triphenylphosphine (48mg, 0.18mmol, 9%), and sodium carbonate (254mg, 2.40mmol, 1.2equiv) in 10% i-PrOH/water (20mL) was heated to 80°C in a sealed vessel under argon for 4h. The mixture was then cooled and filtered through celite. The filtrate was diluted with EtOAc (100mL) and washed with water (45mL). The organic layer was dried (MgSO4), filtered, and evaporated. The crude solid was purified by preparative TLC using 1% AcOH in EtOAc to provide 117mg (34%) of product as a white solid: Rf 0.11 (25% EtOAc/hexane; mp >300°C; 1H NMR (DMSO-d6) δ 12.12 (br s, 1H), 8.91 (d, 1H), 8.55 (d, 1H), 8.1-8.06 (m, 1H), 7.47 (dd, 1H), 7.28-7.20 (m, 3H), 3.90 (s, 3H), 2.82 (t, 2H), 2.52 (t, 2H, partially under DMSO).
  • 9
  • [ 1261675-06-2 ]
  • [ 1528735-24-1 ]
  • [ 1528735-58-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; General procedure: Mixtures of 4-(di-tert-butoxycarbonylamino)-6-amino-2-methylquinoline (100mg, 0.27mmol), the respective carboxylic acid (0.53mmol, 2equiv), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 190mg, 0.500mmol, 2.0equiv) and di-iso-propylethylamine (0.5mL, 2.9mmol, 10equiv) in DMF (5mL) were stirred at room temperature for 16h. The mixtures were poured into 50mL of 5% aq Na2CO3 and extracted with EtOAc (3×50mL). The combined organic layers were washed with 5% aq Na2CO3 (1×50mL), brine (1×50mL), dried (MgSO4), and evaporated. The residual materials were co-evaporated with diethyl ether and treated without further purification with 1:1 TFA/DCM (5mL) for 30min-2h. Removal of solvents gave crude materials as solids or oils that were triturated with diethyl ether and recrystallized from CH3CN/MeOH) to yield the final product as a TFA salt or purified using prep TLC (80:18:2 CHCl3/MeOH/aq CH3NH2) to provide the free base. Some of the free bases were further reacted with a slight excess of p-toluenesulfonic acid in diethyl ether to provide the corresponding p-TsOH salts.
  • 10
  • [ 1261675-06-2 ]
  • [ 1528735-24-1 ]
  • N-(4-amino-2-methylquinolin-6-yl)-3-(4-bromo-2-methoxyphenyl)propionamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: dichloromethane
  • 11
  • [ 1261675-06-2 ]
  • [ 74-88-4 ]
  • [ 1261653-54-6 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; C.C.1.60.C.1.60.1 C.1.60.1. Methyl 3-(4-bromo-2-methoxyphenyl)propanoate To a solution of 3-(4-bromo-2-methoxyphenyl)propanoic acid (1.000 g, 3.86 mmol) in anh. DMF (10 mL) at RT are added cesium carbonate (2.515 g, 7.72 mmol) and iodomethane (0.485 mL, 7.72 mmol) and the mixture is stirred at RT, under nitrogen, for 1 h. Water and Et20 are added and the layers are separated. The aqueous layer is extracted twice with Et20 and the combined organic layers are washed with brine, dried over anh. MgSC>4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords methyl 3-(4-bromo-2-methoxyphenyl)propanoate as a clear oil (0.899 g, 85%). LC-MS B: tR = 0.96 min; no ionization.
85% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; A.2.67.1 A.2.67. 1. Methyl 3-(4-bromo-2-methoxyphenyl)propanoate To a solution of 3-(4-bromo-2-methoxyphenyl)propanoic acid (1.000 g, 3.86 mmol) in anh. DMF (10 mL) atRT are added cesium carbonate (2.515 g, 7.72 mmol) and iodomethane (0.485 mL, 7.72 mmol) and themixture is stirred at RT, under nitrogen, for 1 h. Water and Et20 are added and the layers are separated. Theaqueous layer is extracted twice with Et20 and the combined organic layers are washed with brine, driedover anh. MgSO4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords methyl 3-(4-bromo-2-methoxyphenyl)propanoate as a clear oil (0.899 g, 85%). LC-MS B: tR = 0.96 mm; no ionization.
85% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; I.A.3.63.1 A.3.63.1. Methyl 3-(4-bromo-2-methoxyphenyl)propanoate To a solution of 3-(4-bromo-2-methoxyphenyl)propanoic acid (1.000 g, 3.86 mmol) in anh. DMF (10 mL) at RT are added cesium carbonate (2.515 g, 7.72 mmol) and iodomethane (0.485 mL, 7.72 mmol) and the mixture is stirred at RT, under nitrogen, for 1 h. Water and Et20 are added and the layers are separated. The aqueous layer is extracted twice with Et20 and the combined organic layers are washed with brine, dried over anh. MgS04, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords methyl 3-(4-bromo-2-methoxyphenyl)propanoate as a clear oil (0.899 g, 85%). LC-MS B: tR = 0.96 min; no ionization.
  • 12
  • [ 1261675-06-2 ]
  • methyl 3-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C / Inert atmosphere
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