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[ CAS No. 1878-91-7 ] {[proInfo.proName]}

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Chemical Structure| 1878-91-7
Chemical Structure| 1878-91-7
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Product Details of [ 1878-91-7 ]

CAS No. :1878-91-7 MDL No. :MFCD00093070
Formula : C8H7BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :SZEBGAQWWSUOHT-UHFFFAOYSA-N
M.W : 231.04 Pubchem ID :74657
Synonyms :
Chemical Name :4-Bromophenoxyacetic acid

Calculated chemistry of [ 1878-91-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.21
TPSA : 46.53 ?2

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) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 1.79
Log Po/w (SILICOS-IT) : 1.76
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.238 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.196 mg/ml ; 0.00085 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.387 mg/ml ; 0.00167 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 1878-91-7 ]

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 [ 1878-91-7 ]

* 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 [ 1878-91-7 ]

[ 1878-91-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 1878-91-7 ]
  • [ 4841-23-0 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; at 20℃; for 20h;Inert atmosphere; 2-(4-Bromophenoxy)-acetic acid 16 (1.0 g, 4.3 mmol) was added to a 3 M methanolic solution of hydrochloride (3 mL). The mixture was stirred for 20 h at room temperature under inert atmosphere. The solvent was removed under reduced pressure and the residual oil was dissolved in dichloromethane (15 mL) and was washed successively with water (10 mL), a saturated bicarbonate solution (10 mL) and then again with water (10 mL). The organic phase was dried over magnesium sulfate, filtered and then concentrated under reduced pressure to give compound 17a in the form of a colorless oil, which was sufficiently pure to be used in the rest of the synthesis without additional purification (1 g, 95%). 1H NMR (400 MHz, CDCl3) delta: 7.31 (d, J=8.5 Hz, 2H), 6.78 (d, J=8.5 Hz, 2H), 4.55 (s, 2H), 3.80 (s, 3H); 13C NMR (176 MHz, CDCl3) delta: 169.3, 157.1, 132.7, 116.7, 114.3, 65.6, 52.6; HRMS (ESI+) calculated for C9H9O3BrNa [M+Na]+, m/z 266.9633. found: 266.9622; Rf=0.65 (silica; cyclohexane-ethyl acetate 1:1).
  • 2
  • [ 1878-91-7 ]
  • [ 16738-06-0 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride;N,N-dimethyl-formamide; at 0 - 20℃; for 1h; Example 29; 2-[(Biphenyl-4-yloxy)acetyI]aminothiophene-3-carboxylic Acid; a) Methyl 2-[(4-Bromophenoxy)acetyl]aminothiophene-3-carboxylate; To a stirred solution of <strong>[1878-91-7](4-bromophenoxy)acetic acid</strong> (5.0 g, 0.022 mol) in dry methylene chloride (80 mL) at 0 0C was added catalytic amount of DMF (5 drops) followed by oxalyl chloride (5.5 mL, 0.065 mol). The resulting yellow solution was stirred at room temperature for 1 h and concentrated under reduced pressure to give the desired acid chloride as a yellow solid which was used directly for next step of reaction. Methyl 2- aminothiophene-3-carboxyIate (3.4 g, 0.022 mol) and a 1.0 M solution of sodium bicarbonate EPO <DP n="52"/>in water (30 niL) were sequentially added to a solution of the acid chloride in methylene chloride. The mixture was stirred at room temperature overnight. To the reaction mixture methylene chloride (100 mL) and water (80 mL) were added. The organic layer was separated and the aqueous layer was extracted with methylene chloride (2 x 100 mL). The combined organic solution was dried, filtered and concentrated to give 7.4 g (92%) of product as a yellowish solid. LC-MS 369.9 (M+l).
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 1h; To a solution of 4-Bromophenoxyacetic acid (1.20 g, 4.66 mmol) in anhydrous dichioromethane (10 mL) was added oxalyl chloride (0.59 g, 4.66 mmol)followed by a few drops of N,N-dimethylformamide at 0 C. After stirring at room temperature for one hour, a solution of 4-[(4-ethylpiperazin-1-yl)methyl]-3- (trifluoromethyl)aniline (2.50 g, 8.69 mmol) and triethylamine (2.63 g, 26.0 mmol) in anhydrous dichloromethane (10 mL) was added dropwise at 0 C and warmed to room temperature. After 16 h, the reaction mixture was partitioned between water (200 mL)and dichloromethane (100 mL). The aqueous layer was further extracted with dichloromethane (100 mL). The combined organic extracts were washed with brine (400 mL), dried (Na2SO4), the solvent evaporated and the residue purified by flash chromatography (Redisep silica gel, 97:3 CH2C12/MeOH) to afford 2-(4-bromophenoxy)- N- {4-[(4-ethylpiperazin- 1 -yl)methyl] -3 -(trifluoromethyl)phenyl } -acetamide (2.60 g).
With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 1h; General procedure: To a 0 C stirring solution of substituted aryloxyacetic acid (4a-f, 5.4mmol) in anhydrous dichloromethane (50 mL) was slowly added oxalyl chloride (8 mmol) dropwise. After the reagent addition was complete, the ice bath was removed and the solution was allowed to stand at room temperature for 1 h. The solvent was removed under vacuum to obtain corresponding acyl chloride 5a-f sufficiently pure to be used directly in the next step of the reaction. To a stirred solution of corresponding 1-(substitutedbenzhydryl)piperazine (9a-d, 8mmol), triethylamine (6.8 mL) in dry acetone (30 mL) was slowly added acyl chloride 5a-f, dissolved in anhydrous acetone (30 mL). The mixture was stirred at room temperature for 16h and filtered off. The filtrate was evaporated and purified by column chromatography with AcOEt/petroleum ether (2/1) to give diphenylmethyl-substituted aryloxy acetylpiperazine analogs 10a-s, yield of33-84%.
With thionyl chloride; N,N-dimethyl-formamide;Reflux; Equimolar (5-7 mmol) NaOH and substituted phenol was dissolved in 15 mL water followed by the addition of equimolar (5-7 mmol) NaOH and bromoacetic acid in 15 mL water. The solution was refluxed for 4-8 h, allowed to cool to RT, acidified with concentrated H2SO4 and extracted with ethyl acetate (3×15 mL). The organic layer was extracted with saturated NaHCO3 (3×20 mL). The aqueous layer was acidified with con. HCl followed by extraction with ethyl acetate (3×15 mL), dried over anhydrous MgSO4 and solvent removed under vacuum resulting in the substituted phenoxyacetic acid (e.g., compound 1d of Scheme 1, above). A solution of the phenoxyacetic acid in 20 mL SOCl2 and a drop of dimethyl formamide was refluxed for 3-6 h then excess SOCl2 removed by distillation to give the crude acyl chloride (e.g., compound 1e of Scheme 1, above). A solution of acyl chloride in 15 mL anhydrous acetone was added to a solution of sodium isothiocyanate in ice cold anhydrous acetone and stirred at RT for 3 h to give the acyl isothiocyanate followed by the addition of 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide. After stirring overnight, the solution was poured onto ice and recrystallized in dichloromethane and methanol to give the thiourea product. 4-Bromophenol (1 g, 5.8 mmol) to afford 10 <strong>[1878-91-7](4-bromophenoxy)acetic acid</strong> (1.27, 95%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.41 (d, J=11.1 Hz, 2H), 6.81 (d, J=9.1 Hz, 2H), 4.67 (s, 2H). 10 <strong>[1878-91-7](4-bromophenoxy)acetic acid</strong> (1.5 g, 6.5 mmol) to afford the title thiourea (0.06 g, 2%) as a white 12 solid. 1H NMR (400 MHz, DMSO-d6) delta 12.30 (s, 1H), 11.76 (s, 1H), 8.04 (d, J=8.7 Hz, 2H), 7.90 (d, J=8.7 Hz, 2H), 7.53 (d, J=9.04 Hz, 2H), 7.00 (d, J=9.08 Hz, 2H), 6.81 (s, 1H), 4.95 (s, 2H), 2.31 (1, 6H). 13C NMR (DMSO-d6) delta 178.3, 169.6, 157.0, 132.2, 128.6, 123.5, 116.8, 112.7, 66.1.

  • 3
  • [ 2555-49-9 ]
  • [ 1878-91-7 ]
  • 4
  • [ 106-41-2 ]
  • [ 79-11-8 ]
  • [ 1878-91-7 ]
YieldReaction ConditionsOperation in experiment
78% General procedure: A mixture of NaOH (0.04 mol, 1.60 g), deionized water (20 mL) and ethanol (20 mL) were poured into a 150 mL three-necked flask, then phenol (0.04 mol, 3.76 g) was slowly added under stirring. Twenty minutes later, the above sodium chloroacetate was added dropwise. The reaction solution was heated to 105 C and refluxed for 5 h. After cooling down, the pH value of the mixture was acidified to 1-2 with diluted hydrochloric acid. The precipitate was collected by filtration and washed with diluted hydrochloric acid many times. Recrystallized and dried under a vacuum, resulting in a white solid product of the phenoxyacetic acid (4a).
77% General procedure: Compounds B1-7 were prepared by similar procedures. In atypical synthesis of B1, monochloroacetic acid (0.04 mol,3.78 g) was dissolved in deionized water (15 mL) under thecondition of stirring and an ice bath. Then NaOH (25 %) wasadded dropwise until the pH value was adjusted to 9-10, thena solution of sodium chloroacetate was obtained. To a solutionof NaOH (0.03 mol, 1.20 g), deionized water (15 mL) andethanol (5 mL), phenol (0.04 mol, 3.76 g) was slowly addedunder stirring. After addition, the mixture was stirred for20 min, then the above sodium chloroacetate was addeddropwise, and heated to 105 C and refluxed for 5 h. Thereaction mixture was cooled to room temperature. The pHvalue of the mixture was acidified to 1-2 with diluted hydrochloricacid. The precipitate was filtered, washed with dilutedhydrochloric acid many times, and recrystallized and dried invacuum, resulting in a white solid product of thephenoxyacetic acid (B1)
To a solution of 1 (1 eq.) and chloro-acetic acid (0.9 eq) and acetone was added NaOH (5eq).The reaction mixture was heated at reflux for 4 h, concentrated in vacuo and the residue was diluted in 50 mL of water, stirred and acidified with 6M HCl. An oil was formed, from which the water was decanted. The oil solidified on standing and the resultant solid was washed with water and petroleum ether, and dried in vacuo to give (2) as shown in the scheme above
General procedure: Equimolar quantities of chloroacetic acid (0.05 mol) and appropriate phenol (6k-s) (0.05 mol) were taken in a conical flask, to which aqueous solution of NaOH (0.12 mol in 25 mL water) was slowly added with constant stirring. The solution was stirred for 2 h until the solution turned clear, brown or yellow and then the reaction mixture was evaporated in an evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified by adding con. HCl. The precipitated aryloxy acetic acid was filtered and recrystallized from water or ethanol.
With sodium hydroxide; In water; General procedure: Equimolar quantities of 2-chloro acetic acid/3-chloro propionicacid (0.05 mol) and appropriate phenol (1a-q) (0.05 mol) were taken in a conical flask, to which aqueous solution of NaOH(0.12 mol in 25 mL water) was slowly added with constant stirring.The solution was stirred for 2 h until the solution turned clear,brown or yellow and then the reaction mixture was evaporatedin a evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified byadding con. HCl. The precipitated aryloxy acetic/propionic acidwas filtered and recrystallized from water or ethanol
With sodium hydroxide; In water; at 85 - 90℃; for 2h; General procedure: Overall the phenoxyacetic acids were commercially available, except for 4-methylphenoxyacetic acid and 4-methoxyphenoxyacetic acid. The latter phenoxyacetic acids were synthesized via a general synthetic route as described elsewhere [1,2,3]. In short, the appropriate substituted phenol (20 mmol) was added to anaqueous solution of NaOH (10 mL). Chloroacetic acid (34 mmol) was added and the reaction was heated (85-90 C) under reflux for 2 h and subsequently cooled to room temperature to yield a thick precipitation with a pH of 12. The reaction was acidified with concentrated HCl to a pH of 2 and extracted to diethyl ether (100 mL). The organic phase was extracted thrice with 100 mL of sodium carbonate solution (5%). The pooled aqueous phases were acidified to a pH of 2 with HCl to yield a precipitate. The desired phenoxyacetic acid was collected by filtration and left to dry overnight in the fume hood. Analytical pure samples were obtained after recrystallization from methanol.

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