23676-08-6|Methyl 4-ethoxybenzoate| Ambeed

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Quality Control of [ 23676-08-6 ] Purity: 98% SDS Specification

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Product Details of [ 23676-08-6 ]

CAS No. :	23676-08-6
Formula :	C₁₀H₁₂O₃
M.W :	180.20
SMILES Code :	O=C(OC)C1=CC=C(OCC)C=C1
MDL No. :	MFCD00017264
InChI Key :	RNHXTCZZACTEMK-UHFFFAOYSA-N
Pubchem ID :	90231

Safety of [ 23676-08-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312-P330

Computational Chemistry of [ 23676-08-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	49.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.53
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.87
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.94
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.7
Solubility	0.361 mg/ml ; 0.002 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.04
Solubility	0.166 mg/ml ; 0.000919 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.0
Solubility	0.178 mg/ml ; 0.000989 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.52 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.32

Application In Synthesis of [ 23676-08-6 ]

* 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 [ 23676-08-6 ]

[ 23676-08-6 ] Synthesis Path-Downstream 1~35

1
[ 619-86-3 ]
[ 23676-08-6 ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 3960.

2
[ 908094-01-9 ]
[ 619-86-3 ]
[ 23676-08-6 ]

References: [1]Magnetic Resonance in Chemistry,1989,vol. 27,p. 585 - 591.
[2]Organic Letters,2015,vol. 17,p. 5276 - 5279.

3
[ 98546-40-8 ]
[ 922-67-8 ]
[ 23676-08-6 ]
[ 108593-47-1 ]

References: [1]Chemische Berichte,1987,vol. 120,p. 1339 - 1346.

4
[ 6018-41-3 ]
[ 927-80-0 ]
[ 23676-08-6 ]

References: [1]Chemische Berichte,1987,vol. 120,p. 1347 - 1356.

5
[ 23676-08-6 ]
[ 60175-29-3 ]
1-(4'-Decyl-biphenyl-4-yl)-3-(4-ethoxy-phenyl)-propane-1,3-dione [ No CAS ]

References: [1]Molecular Crystals and Liquid Crystals (1969-1991),1987,vol. 151,p. 93 - 108.

6
[ 23676-08-6 ]
[ 619-86-3 ]

Yield	Reaction Conditions	Operation in experiment
98.40%		General procedure: To the stirred solution of the ester was prepared above treated with sodium hydroxide (2.0 eq) in methanol at 60-65 C for 3 h. Acidified the reaction mixture with hydrochloric acid and isolated the corresponding product in good yield and methanol was recovered.
	With potassium hydroxide; In ethanol; water; for 2h;Reflux;	General procedure: 4-dodecyloxy methylbenzoate(13.3 g, 0.04mol)was placed in a one liter single-necked round-bottom flask equippedwith double wall water condenser. Ethanol (250 ml) and potassium hydroxide (6 g, 0.1 mol)dissolved in distilled water (250 ml) were added to the flask. The solution was refluxed for2 hours and allowed to cool down at r.t. and then neutralized with 10% hydrochloric acidto get a white precipitate. It was purified by recrystallizing from methanol.
	With potassium hydroxide; In ethanol; water; for 2h;Reflux;	General procedure: 4-n-alkoxy benzoic acids (3c) were prepared by dissolving comp.3b in ethanol (40 ml) and10% aq.KOH(2ml)was added. The resultant mixturewas heated at reflux for 6 to 7 hours thencooled to room temperature, poured into ice cold water (80 ml) and then acidified with dil.HCl. The crude product obtained by filtration was recrystallized by usingMeOH/DCM [51].

With potassium hydroxide; In ethanol; water;Reflux;

General procedure: 4-n-alkoxy benzoic acids (3c) were prepared by dissolving comp.3b in ethanol (40 ml)and 10% aq. KOH (2 ml) was added. The resultant mixture was heated at reflux for 6 to 7 hours then cooled to room temperature, poured into ice cold water (80 ml) and thenacidified with dil.HCl. The crude product obtained by filtration was recrystallized byusing MeOH/DCM

References: [1]Asian Journal of Chemistry,2018,vol. 30,p. 85 - 88.
[2]Journal of Organic Chemistry,1981,vol. 46,p. 1991 - 1993.
[3]Journal of Organic Chemistry,2021,vol. 86,p. 4254 - 4261.
[4]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1995,vol. 268,p. 21 - 44.
[5]Journal of Mass Spectrometry,2008,vol. 43,p. 1224 - 1234.
[6]Molecular Crystals and Liquid Crystals,2013,vol. 582,p. 1 - 14.
[7]Langmuir,2015,vol. 31,p. 10831 - 10842.
[8]Molecular Crystals and Liquid Crystals,2017,vol. 656,p. 32 - 47.
[9]Molecular Crystals and Liquid Crystals,2018,vol. 665,p. 100 - 118.
[10]Molecular Crystals and Liquid Crystals,2019,vol. 681,p. 58 - 70.
[11]Molecular Crystals and Liquid Crystals,2019,vol. 682,p. 8 - 26.

7
[ 74-96-4 ]
[ 99-76-3 ]
[ 23676-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 4.5h;	General procedure: In a representative experiment,4-hydroxy methyl benzoate (7.6 g, 0.05 mol) was placed in a 500 mlthree-necked round-bottom flask equipped with stirrer and thermometer. To that, N,N-dimethylformamide (150 ml) and potassium carbonate (10.36 g, 0.075 mol) were added.The resulting mixture was stirred while maintaining the temperature at 90C, then nbromododecane(12 ml, 0.05 mol) was added through a pressure equalizing droppingfunnel over a period of 30 minutes and the stirring was continued for about 4 hours andthen the reaction mixture was allowed to cool down at r.t. poured into a 2-l beaker [16].The contents were diluted with water (250 ml) and then transferred to a 500 ml separatingfunnel and diethyl ether was added. The ether layer collected was washed twice using 10%potassium hydroxide solution and followed by distilled water. The organic layer was driedwith anhydrous sodium sulfate. Upon evaporation of ether, 4-dodecyloxy methyl benzoateresulted as a liquid.
	With potassium hydroxide; In methanol;Reflux;	General procedure: Methyl-4-n-alkoxy benzoate(3b) were prepared by alkylation of Methyl-4-hydroxy benzoate(3b) with alkyl bromide (R-Br) in MeOH (C1 to C8) and EtOH (C10 to C18) and reflux at3 to 4 hrs. and then dump into ice-cold water to get final Methyl-4-n-alkoxy benzoate (3b)derivatives [50].
	In methanol;Reflux;	General procedure: Methyl-4-n-alkoxy benzoate(3b) were prepared by alkylation of Methyl-4-hydroxybenzoate (3b) with alkyl bromide (R-Br) in MeOH (C1 to C8) and EtOH (C10 to C18)and reflux at 3 to 4 hrs. and then dump into ice-cold water to get final Methyl-4-nalkoxybenzoate (3b) derivatives

References: [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1995,vol. 268,p. 21 - 44.
[2]Journal of Mass Spectrometry,2008,vol. 43,p. 1224 - 1234.
[3]Molecular Crystals and Liquid Crystals,2013,vol. 582,p. 1 - 14.
[4]Langmuir,2015,vol. 31,p. 10831 - 10842.
[5]Molecular Crystals and Liquid Crystals,2017,vol. 656,p. 32 - 47.
[6]Molecular Crystals and Liquid Crystals,2018,vol. 665,p. 64 - 81.
[7]Molecular Crystals and Liquid Crystals,2018,vol. 665,p. 100 - 118.

8
[ 67-56-1 ]
[ 619-86-3 ]
[ 23676-08-6 ]

Yield	Reaction Conditions	Operation in experiment
88.7%	With sulfuric acid; for 0.133333h;Microwave irradiation;	General procedure: The methyl benzoates, 2a-h were prepared following reportedmethod27 (Table 1).Microwave method: The same procedure as stated abovewas adopted using 100 ml methanol following the other conditionsof microwave irradiated esterification in reactor at 350Watt (power) for 5-8 min. All the esters were recrystallizedusing rectified spirit except 2a, a fluoro compound which wasa liquid (Table 1).
	With sulfuric acid; for 4h;Reflux;	General procedure: Each substituted benzoic acid (1) (0.04 mol) was heated at reflux for 4 hours in 50.0 mL (1.23 mol) of anhydrous methanol and 1.0 mL (2.0 mmol) of sulfuric acid. The solvent was concentrated and the product obtained washed with cold water. In some cases, as for non-substituted compounds, the ester showed an oily aspect and, to promote its precipitation, the compound was cooled by immersion in dry ice-ethanol bath.
60%Spectr.	With monolith-SO3H; In toluene; at 80℃; for 24h;Inert atmosphere;	General procedure: To atest tube were added the carboxylic acid (500 mol), monolith-SO3H (100 wt%), and toluene (0.5 mL). Then, MeOH (30.3 L,750 mol) and additional toluene (0.5 mL) were added. Thereaction mixture was stirred under an Ar atmosphere (balloon)at 80 C for 24 h, then passed through a cotton filter to removemonolith-SO3H and washed with Et2O (15 mL). The filtratewas concentrated in vacuo. The residue was purified by silica gel flash column chromatography (n-hexane/Et2O) to give thecorresponding methyl ester, if necessary. The 1H and 13CNMRspectra of the product were identical to those in the literature.

References: [1]Journal of the Indian Chemical Society,2018,vol. 95,p. 661 - 666.
[2]Bollettino Chimico Farmaceutico,1997,vol. 136,p. 244 - 249.
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6292 - 6301.
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 2423 - 2435.
[5]Pharmaceutical Chemistry Journal,2018,vol. 51,p. 907 - 917.
[6]Bulletin of the Chemical Society of Japan,2021,vol. 94,p. 2702 - 2710.

9
[ 23676-08-6 ]
[ 58586-81-5 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With hydrazine hydrate; In methanol; for 0.0833333h;Microwave irradiation;	General procedure: The benzoic acid hydrazides, 3a-h were prepared accordingto reported method in literature28,29 with some desirablemodifications. The ester (2a-h, 0.1 mol) dissolved inappropriate volume of methanol was transferred to a flaskwith a reflux condenser. Hydrazine hydrate (99%, 0.15 mol) was slowly added to the mixture and then kept on reflux forabout 5-6 h. The excess of solvent and hydrazine hydratewere distilled off. On addition of water the product separatedout which was washed several times with distilled water anddried. The product was recrystallized from 80% aqueous ethanoland melting points determined (Table 2).Microwave method: The same procedure as stated abovewas adopted using 100 ml methanol following the other conditionsof microwave in a microwave reactor at 350 Watt(power) for 3-5 min. Precipitation and separation of precipitatewas done as for conventional method (Table 2).
	With hydrazine hydrate; In water; at 75℃; for 0.166667h;	General procedure: Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 C. The methyl ester 3 (0.01 mol) was added and the mixture was heated at reflux for 10 min. The cooling was performed sequentially in water bath, followed by ice bath and dry ice-ethanol bath. The precipitate was filtered and washed with cold water.
	With hydrazine hydrate; In methanol; at 10 - 80℃; for 6h;	General procedure: 13.5 mmol of the methyl benzoate derivatives were added to 100 mL of methanol at the 250 mL double-mouth bottle. Add 6.75 mL (108 mmol) of hydrazine hydrate to the reactive mixture gradually between 10 and 25 C over 2 h. Then the temperature increased to 80 C and refluxed for 4 h, subsequently lowered to room temperature. After the methanol is removed by decompression concentration, 300 mL of added water was mixed at 5 C to decrystallize, and the white solid (b) is obtained by filtration and drying.

References: [1]Journal of the Indian Chemical Society,2018,vol. 95,p. 661 - 666.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4842 - 4850.
[3]Bollettino Chimico Farmaceutico,1997,vol. 136,p. 244 - 249.
[4]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6292 - 6301.
[5]Pharmaceutical Chemistry Journal,2018,vol. 51,p. 907 - 917.
[6]Bioorganic and Medicinal Chemistry Letters,2021,vol. 34.
[7]Pharmaceutical Chemistry Journal,2021,vol. 55,p. 556 - 565.

Yield	Reaction Conditions	Operation in experiment
88%		EXAMPLE 3 Preparation of methyl 4-ethoxybenzoate Cupric chloride dihydrate (0.125 g; 0.733 m. moles) and 1,10-phenanthroline hydrate (0.375 g; 1.9 m. moles) were added to a solution of sodium (1.15 g; 50 m. moles) in methanol (75 ml). A stream of dry oxygen was passed through the mixture, 1-(4-ethoxyphenyl)-2,2,2-trichloroethanol (11.72 g; 43.6 m. moles) added and the mixture stirred at 30-35 C. for 1 hour. The reaction mixture was diluted with water (200 ml), acidified with hydrochloric acid and extracted with ether (3*50 ml). The combined ether extracts were washed with dilute aqueous sodium carbonate and water, dried (MgSO4) and evaporated. The residue was distilled to give methyl 4-ethoxybenzoate (7.5 g; yield 88%), b.p. 142-143 C./12 mm, m.p. 35-37 C. Analysis: Calculated for C10 H12 O3: C 66.65; H 6.7%. Found: C 66.9; H 6.7%.
88%		EXAMPLE 4 Preparation of methyl 4-ethoxybenzoate Cupric chloride dihydrate (0.064 g; 0.38 m. mole) and 2,2'-bipyridyl (0.15 g; 0.96 m. mole) were added to a solution of sodium (0.582 g; 25.3 m. moles) in methanol (42 ml) and a stream of dry oxygen was passed through the stirred mixture. 1-(4-Ethoxyphenyl)-2,2,2-trichloroethanol (6.9 g; 25.4 m. moles) was added and the mixture heated (bath temp. 30-25 C.) for a period of 11/4 hours. The reaction mixture was then diluted with water (100 ml), acidified with hydrochloric acid and extracted with ether (3*50 ml). The combined ether extracts were washed with saturated aqueous sodium carbonate (50 ml) and water (50 ml), dried (MgSO5) and evaporated. The residue was distilled to give methyl 4-ethoxybenzoate (4.05 g; 88%), b.p. 143 C./12 mm.
85%	Sealed tube; Inert atmosphere;	General procedure: 1. To an oven-dried 10-50 mL test-tube equipped with a teflon coated magnetic stir bar, carboxylic acid (1 mmol) were added. Then DEE or methanol or ethanol or THF (0-10 ml) were added using a syringe and further the tube was sealed with septa and additional nitrogen balloon placed over the tube. 2. Next, the diazo-methane solution was added through the above designed diazo-pen for 0- 21 min. (equivalent to 1 mmol of diazomethane). 3. After diazo exposure for 0-21 min, product was washed with aq. NaHCCh (3x20 mL), then washed with brine (30 mL). 4. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to provide a formula 5.

11
[ 35387-93-0 ]
[ 20398-06-5 ]
[ 214360-78-8 ]
[ 23676-08-6 ]
methyl 6-methoxy-2',4',6'-trimethylbiphenyl-3-carboxylate [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9655 - 9662.

12
[ 23676-08-6 ]
[ 84159-98-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4842 - 4850.
[2]Pharmaceutical Chemistry Journal,2018,vol. 51,p. 907 - 917.
[3]Journal of the Indian Chemical Society,2018,vol. 95,p. 661 - 666.

13
[ 23676-08-6 ]
2-(4-ethoxy-phenyl)-5-(2-phenyl-[1,3]dioxolan-2-ylmethylsulfanyl)-[1,3,4]oxadiazole [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4842 - 4850.

14
[ 23676-08-6 ]
4-ethoxy-N’-((5-nitrofuran-2-yl)methylene)benzohydrazide [ No CAS ]

References: [1]Bollettino Chimico Farmaceutico,1997,vol. 136,p. 244 - 249.

15
[ 23676-08-6 ]
[ 53146-73-9 ]