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[ CAS No. 14426-42-7 ] {[proInfo.proName]}

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Chemical Structure| 14426-42-7
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Product Details of [ 14426-42-7 ]

CAS No. :14426-42-7 MDL No. :MFCD00957178
Formula : C10H11ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QULRDJFRGVHKLN-UHFFFAOYSA-N
M.W : 214.65 Pubchem ID :26689
Synonyms :

Calculated chemistry of [ 14426-42-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.65
TPSA : 35.53 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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 2.94
Log Po/w (WLOGP) : 2.28
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 2.58
Consensus Log Po/w : 2.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.21 mg/ml ; 0.000977 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.0963 mg/ml ; 0.000449 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.65
Solubility : 0.0484 mg/ml ; 0.000225 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 14426-42-7 ]

Signal Word:Danger Class:9
Precautionary Statements:P273-P280-P301+P312+P330-P305+P351+P338+P310 UN#:3077
Hazard Statements:H302-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14426-42-7 ]

* 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 [ 14426-42-7 ]

[ 14426-42-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 122-88-3 ]
  • [ 64-17-5 ]
  • [ 14426-42-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;Reflux; General procedure: Each substituted benzoic acid or aroyloxy acetic acid (7a-s) 0.088 mol was refluxed for 2-12 h in 2.4 mol of HCl gas saturated anhydrous ethanol. Then a hot solution was poured into 300 mL of water (no hydrochloride separates) to which solid Na2CO3 was added until the solution turns neutral. Precipitated ester was filtered by suction, dried and recrystallized from ethanol or methanol. In case of liquid esters, the neutralized solution was extracted with chloroform (25 mL x 3), the combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a clear liquid.
With sulfuric acid; for 6h;Reflux; General procedure: The substituted acid (0.1 mole) and ethanol (50 ml) were taken with a few drops of concentrated sulfuric acid and it was refluxed for 6 hours.The reaction mixture was concentrated bydistilling of the excess of ethanol under reduced pressure and treated with a saturated solution of sodium bicarbonate. The ester obtained used for the preparation of hydrazide directly. The ester(0.1 mole) was dissolved in appropriate quantity of ethanol and to this hydrazine hydrate (0.1 mole) was added. The reaction mixture was taken in a round bottomed flask and refluxed for a period of 12-18 hours. Excess of ethanol was distilled off under reduced pressure. It was then poured into ice cold water and the solid obtained was filtered. It was crystallized from ethanol.
With acetyl chloride; for 24h;Cooling with ice; Reflux; General procedure: Compounds D1-7 were prepared by similar procedures. In atypical synthesis of D1, a mixture of phenoxyacetate(10 mmol, 1.80 g), hydrazine hydrate (80 %, 5 mL) and absoluteethanol (30 mL) was added to a 150 mL three-neckflask, then the reaction mixture was refluxed for 5 h. Themixture was cooled to room temperature. The crude productwas collected by filtration and washed several times with ethanol.After drying, white needle crystal was recrystallizedfrom ethanol and dried in vacuum
With sulfuric acid;Reflux; General procedure: The aryl/aralkyl organic acids (5.0 g, 1a-k), the absolute ethanol (20 mL), and conc.H2SO4 (1.5 mL) were taken in 250 mL round bottom flask fitted with reflux condenser. Thereaction mixture was refluxed for 3-4 h. TLC was used to check the completion of reactionby using a solvent system, n-hexane, and EtOAc. On completion, reaction contents were transferred to a separating funnel containing distilled H2O (20 mL). Sodium carbonate(Na2CO3) solution was added to neutralize the acidic pH. Diethyl ether was added to theseparating funnel followed by shaking and the contents were left to set up two layers. Thelower aqueous layer was discarded and the upper organic ether layer containing requiredester was taken into the distillation flask. The organic layer, diethyl ether was distilled offand the corresponding esters (2a-k) were collected from the flask to follow the furtherreaction.17-19

  • 2
  • [ 122-88-3 ]
  • [ 14426-42-7 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride; In ethanol; Preparation of ethyl (4-chlorophenoxy) acetate (D35) STR61 A solution of (4-chlorophenoxy) acetic acid (21.1 g, 0.113 mole) in ethanol (250 ml) containing five drops of concentrated hydrochloric acid, was heated under reflux for 21/2 h. The solution was allowed to cool, concentrated to about a third of its volume, and then diluted with water (500 ml). The mixture was extracted with ether (2*250 ml) and the organic solution washed with 10% sodium carbonate solution (2*150 ml), dilute hydrochloric acid (2*150 ml) and brine (2*150 ml); then dried and evaporated to dryness to leave a pale yellow oil. This crystallized on standing to give the title compound as a beige solid (21.5 g, 90%). NMR: delta (CDCl3) 1.27 (t, J=7 Hz, 3H), 4.21 (q, J=7 Hz, 2H), 4.53 (s, 2H), 6.82 (d, J=9 Hz, 2H), 7.26 (d, J=9 Hz, 2H).
  • 3
  • [ 14426-42-7 ]
  • [ 122-88-3 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide; In ethanol; water;Reflux; General procedure: Compounds (3a-j,0.02mol) were dissolved in ethanol (15mL), sodium hydroxide (0.035mol) in water (5mL) was added, and the mixture was refluxed for 5-9h. The reaction mixture was cooled and acidified with 2N hydrochloric acid. The precipitate was filtered, washed with water, and finally recrystallized from methanol to afford desired compounds (4a-j). Compound (4a) is takenas a representative example to explain physical and characterization data.
77% To a solution of ethyl [(4-chlorophenyl)oxy]acetate (Intermediate 2) (60 g, 0.28 mol.) in methyl alcohol was added a solution of potassium hydroxide (28 g, 0.5 mol.) in water.The solution was heated at 700C overnight. After concentration under reduced pressure, the mixture was cooled with iced water and concentrated HCI (20 ml, 10 M) was added. The resulting solid material was filtered and dried to give the title compound as a white solid (40 g, 77%).1H NMR (300 MHz, CDCI3, ppm) delta: 7.3 (d, 2H), 6.9 (d, 2H), 4.6 (s, 2H).
With sodium hydroxide; In methanol; at 20℃; for 1h; General procedure: To a stirred solution of 4j (2.5 g, 9.8 mmol) in MeOH (30 mL) was added 3N NaOH solution (13.1 mL, 39.3 mmol). After being stirred at room temperature for 1 h, the mixture was diluted with water (100 mL), acidified with 3N HCl, and extracted with dichloromethane (100 mL × 2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title compound (2.12 g, 97% yield) . 1H NMR (300MHz, DMSO-d6) delta 7.49(d, J = 8.8 Hz, 1H), 7.21 (s, 1H), 6.92 (d, J = 8.8 Hz, 1H),4.73 (s, 2H).
With water; sodium hydroxide; In ethanol; at 20℃; for 4h; General procedure: A solution of corresponding substituted ethylaryloxyacetate (3a-f, 25 mmol) in ethanol (100 mL) was treated with 10% aqueous sodium hydroxide (9 mmol). After 4 h at room temperature and evaporation under reduced pressure of ethanol, the aqueous phases were acidified at pH 4 with HCl (2 N). Removal of precipitate by filtration yielded the crude acids, which were recrystallized in ethanol to afford substituted aryloxyacetic acid 4a-f, yield 66-90%.

  • 4
  • [ 14426-42-7 ]
  • [ 10563-23-2 ]
  • <4-Chlorphenoxy>-essigsaeure-<3-ethylaminopropylamid> [ No CAS ]
  • 5
  • [ 14426-42-7 ]
  • [ 102-83-0 ]
  • [ 6738-01-8 ]
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