[ CAS No. 404-98-8 ] {[proInfo.proName]}

Name: 404-98-8|2-(3-Fluorophenoxy)acetic acid|97%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 404-98-8 ]

CAS No. :	404-98-8	MDL No. :	MFCD02295721
Formula :	C₈H₇FO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DMYZZZCPJOWSNT-UHFFFAOYSA-N
M.W :	170.14	Pubchem ID :	1545717
Synonyms :

Calculated chemistry of [ 404-98-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.47
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	1.48
Log Po/w (WLOGP) :	1.71
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.52

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.0
Solubility :	1.7 mg/ml ; 0.01 mol/l
Class :	Very soluble
Log S (Ali) :	-2.06
Solubility :	1.47 mg/ml ; 0.00863 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	1.1 mg/ml ; 0.00646 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 404-98-8 ]

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

Application In Synthesis of [ 404-98-8 ]

* 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.

Upstream synthesis route of [ 404-98-8 ]
Downstream synthetic route of [ 404-98-8 ]

[ 404-98-8 ] Synthesis Path-Upstream 1~6

1
[ 777-70-8 ]
[ 404-98-8 ]

Reference： [1] Journal of Fluorine Chemistry, 2006, vol. 127, # 2, p. 291 - 295
[2] Patent: US2004/102450, 2004, A1, . Location in patent: Page/Page column 77
[3] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 173 - 179
[4] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 10, p. 2549 - 2552

2
[ 372-20-3 ]
[ 79-11-8 ]
[ 404-98-8 ]

Reference： [1] Journal of the American Chemical Society, 1943, vol. 65, p. 1555
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4336 - 4347
[3] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187

3
[ 372-20-3 ]
[ 105-36-2 ]
[ 404-98-8 ]

Reference： [1] Patent: WO2014/100730, 2014, A1, . Location in patent: Paragraph 00262

4
[ 372-20-3 ]
[ 96-32-2 ]
[ 404-98-8 ]

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387

5
[ 372-20-3 ]
[ 404-98-8 ]

Reference： [1] Journal of Fluorine Chemistry, 2006, vol. 127, # 2, p. 291 - 295
[2] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 173 - 179
[3] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 10, p. 2549 - 2552

6
[ 32376-33-3 ]
[ 79-11-8 ]
[ 404-98-8 ]

Reference： [1] Organic Mass Spectrometry, 1993, vol. 28, # 10, p. 1167 - 1178

[ 404-98-8 ] Synthesis Path-Downstream 1~46

1
[ 404-98-8 ]
[ 396-03-2 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 94,95, 97

2
[ 404-98-8 ]
[ 398-97-0 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1956,vol. 75,p. 186

3
[ 404-98-8 ]
[ 2923-61-7 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 94,95, 97

4
[ 372-20-3 ]
[ 79-11-8 ]
[ 404-98-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: An appropriately substituted phenol (50 mmol) was added to a solution of NaOH (187.5 mmol) in 15 mL of H2O. Chloroacetic acid (85 mmol) was added slowly at to the resulting solution at 40 C and the reaction mixture was heated to 85 C. Stirring was continued for 2 h, the reaction was cooled to room temperature and 100 mL H2O was added. The reaction was filtered and the filtrate was acidified with concentrated HCl to pH 1-2. The brown oil fraction which formed was extracted to diethylether (2 × 50 ml). The ether fraction, in turn, was extracted with an aqueous solution of 5% Na2CO3 (2 × 37.5 ml). The combined Na2CO3 fractions were acidified to pH 1-2 with concentrated HCl and the resulting precipitate was collected by filtration and oven dried to obtain the required acids.24

Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 1555
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4336 - 4347
[3]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 183 - 187

5
[ 67-56-1 ]
[ 404-98-8 ]
[ 129368-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 20℃; for 3h;	To a solution of [(3 -fluorophenyl)oxy] acetic acid (200 mg, 1.175 mmol) in methanol (3 ml) was added thionyl chloride (0.086 ml, 1.175 mmol) and the mixture was stirred at room temperature for 3h. The reaction mixture was evaporated to dryness to give 203 mg of colorless oil.
	With thionyl chloride; at 20℃; for 3h;	To a solution of [(3-fluorophenyl)oxy]acetic acid (200 mg, 1.175 mmol) in methanol (3 ml) was added thionyl chloride (0.086 ml, 1.175 mmol) and the mixture was stirred at room temperature for 3h. The reaction mixture was evaporated to dryness to give 203 mg of colorless oil.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 629 - 631
[2]Journal of the Indian Chemical Society,1981,vol. 58,p. 1082 - 1083
[3]Patent: WO2008/128962,2008,A1 .Location in patent: Page/Page column 64
[4]Patent: WO2009/141399,2009,A1 .Location in patent: Page/Page column 43

6
[ 32376-33-3 ]
[ 79-11-8 ]
[ 404-98-8 ]

Reference： [1]Organic Mass Spectrometry,1993,vol. 28,p. 1167 - 1178

7
[ 404-98-8 ]
[ 2906-12-9 ]
[ 84474-14-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 781 - 783

8
[ 404-98-8 ]
[ 180048-73-1 ]
(3-fluoro-phenoxy)-acetic acid 2-(4-methanesulfonyl-phenyl)-1,1-dimethyl-2-oxo-ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 3181 - 3186

9
[ 777-70-8 ]
[ 404-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; water; In tetrahydrofuran; methanol; for 16h;	B. 3-Fluorophenoxy-acetic acid. To a solution of ethyl 3-fluorophenoxy-acetate (2 g, 10 mmol) in 24 ML of a 1:1:1 solution of MeOH:H2O:THF is added lithium hydroxide monohydrate (2.25 g, 54 mmol).The solution is stirred for 16 hours.After this time, the solution is concentrated under reduced pressure to 1/3 of its volume.The remaining solution is acidified to PH=3 with 1N HCl (aq.).The aqueous solution is extracted with EtOAc. The organic layer is washed with a saturated solution NaCl (aq.).The organic layer is dried over MgSO4, filtered and concentrated to give the product (1.65 g, 9.7 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) delta9.8 (bs, 1H), 7.28 (m, 1H), 6.69 (m, 3H), 4.70 (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).

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 291 - 295
[2]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 77
[3]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 173 - 179
[4]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2549 - 2552

10
[ 404-98-8 ]
[ 95299-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 4h;Reflux;	General procedure: Phenoxyaceticacids (50 mmol) was added to thionylchloride (50 mL) at room temperature under a calcium chloride tube.The mixture was then heated under reflux for 4 h. After cooling to roomtemperature, the mixture was evaporated in vacuo. The residue was dissolved in50 mL of dichloromethaneand aluminium chloride (13 g, 98 mmol) was addedslowly to the solution at 0C. After stirring at 0C for 15min, the reactionstirred at room temperature for 30min. The mixture was then poured into icewater, extracted with portions of ethyl acetate (3×50 mL). The organic layerwas washed with brine, dried over anhydrous sodium sulfate and the solventremoved in vacuo. The residue was purified by column chromatography to get theproduct.

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 291 - 295
[2]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 173 - 179
[3]Tetrahedron Letters,2015,vol. 56,p. 4383 - 4387
[4]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 183 - 187

11
[ 372-20-3 ]
[ 404-98-8 ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 291 - 295
[2]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 173 - 179
[3]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2549 - 2552

12
[ 404-98-8 ]
O,O-dimethyl 1-(3-fluorophenoxyacetoxy)benzylphosphonate [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 291 - 295

13
[ 404-98-8 ]
O,O-dimethyl 1-(3-fluorophenoxyacetoxy)-3-nitrobenzylphosphonate [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 291 - 295

14
N-Methyl-4,5-dimethoxy-2-(1-pyrrolidinyl)cyclohexanamine [ No CAS ]
[ 404-98-8 ]
N-[4,5-dimethoxy-2-(1-pyrrolidinyl)cyclohexyl]-2-(3-fluorophenoxy)-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrachloromethane; thionyl chloride; dichloromethane;	Step 7 Preparation of N-[4,5-dimethoxy-2-(1-pyrrolidinyl)cyclohexyl]-2-(3-fluorophenoxy)-N-methylacetamide <strong>[404-98-8]3-Fluorophenoxyacetic acid</strong> (1.2 mmol) was dissolved in 5 mL of thionyl chloride. The solution was heated under reflux in an oil bath for one hour. At the end of this time, the excess thionyl chloride was removed to yield a sticky oil. This material was dissolved in carbon tetrachloride and the remaining thionyl chloride removed by azeotropic distillation under vacuum. The diamine from Step 6 (1 mmol) was dissolved in 5 mL of dichloromethane and cooled with an ice bath. The crude acid chloride was dissolved in 5 mL of cold dichloromethane, and the resulting solution was slowly added to the solution of diamine. The solid which separated was collected by filtration and purified by high pressure liquid chromatography over silica gel, eluding with dichloromethane/methanol. The title compound was obtained, mp 119-121 C. The proton magnetic resonance spectrum (CDCl3) showed peaks at delta 1.8 (multiplet) delta 2.98 (singlet, 3 protons), delta 3.28 (singlet), delta 3.31 (singlet, 6 protons), delta 4.88 (doublet, 1 proton), delta 5.12 (doublet, 1 proton), and delta 7.20 (multiplet, 4 protons). Using the methods detailed in Example 1 above, the following additional compounds were prepared.

Reference： [1]Patent: US4855316,1989,A

16
[ 5440-00-6 ]
[ 404-98-8 ]
C₁₄H₁₅FN₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The syntheses of 3a-j were accomplished using the literature procedure.22 1,3-Dimethyl-5,6-diaminouracil23 (4 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDAC; 5.36 mmol) were dissolved in 42 mL dioxane/H2O (1:1) and the appropriate phenoxyacetic acid (4 mmol) was added. A thick suspension was obtained and the pH was adjusted to 5-6 with 4 N aqueous HCl. The reaction was stirred for 2 h at room temperature and neutralized with aqueous NaOH (1 N). The precipitate was collected by filtration and subsequently dissolved in 40 mL dioxane/H2O (1:1). The reaction was heated under reflux for 2 h, cooled to 0 C and acidified to a pH of 4 with 4 N aqueous HCl. The resulting precipitate, the corresponding 1,3-dimethyl-8-substituted-7H-xanthinyl analogue, was collected by filtration, washed with 50 mL H2O and dried at 50 C. The 7H-xanthinyl analogue was used in the subsequent reaction without further purification. The corresponding 1,3-dimethyl-8-substituted-7H-xanthinyl analogue (2 mmol) was dissolved in a minimum amount of DMF (approximately 20 mL) at 90 C. K2CO3 (5 mmol), followed by iodomethane (4 mmol), and the reaction mixture was stirred at 90 C for 1 h. The reaction progress was followed with TLC employing neutral alumina sheets and ethyl acetate/dichloromethane (1:1) as mobile phase. The insoluble materials were removed by filtration. H2O (350 ml) was added to the filtrate and the mixture was cooled on ice for 3 h. The precipitate that formed was collected by filtration and dried overnight at room temperature. The products were recrystallized from methanol/ethyl acetate (7:5).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4336 - 4347

17
[ 404-98-8 ]
C₁₄H₁₃FN₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4336 - 4347

18
[ 404-98-8 ]
[ 1388725-79-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4336 - 4347

19
[ 372-20-3 ]
[ 105-36-2 ]
[ 404-98-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred mixture of 3-fluorophenol (100 mg, 0.893 mmol) in MeCN (5 mL) was added ethyl bromoacetate ( 222 mg , 1.34 mmol) and K2C03 (369 mg , 2.68 mmol). The mixture was stirred at 80 C for 4 hours. The mixture was then filtered and the filtrate concentrated. NaOH (71 mg, 1.79 mmol) and watenEtOH (1: 1, 10 mL) was added to the residue and the mixture stirred at 50 C for 4 hours. The mixture was acidified by adding 1M HC1, and then extracted with ethyl acetate (2x30 mL). The combined extracts were washed with brine (30 mL), dried over anhydrous Na2S04 and concentrated. The residue was directly for the next step. LCMS (m/z): 171.0 (M+l).
		To a stirred mixture of 55 3-fluorophenol (100 mg, 0.893 mmol) in 40 MeCN (5 mL) was added 41 ethyl bromoacetate (222 mg, 1.34 mmol) and 19 K2CO3 (369 mg, 2.68 mmol). The mixture was stirred at 80 C. for 4 hours. The mixture was then filtered and the filtrate concentrated. 42 NaOH (71 mg, 1.79 mmol) and 43 water:8 EtOH (1:1, 10 mL) was added to the residue and the mixture stirred at 50 C. for 4 hours. The mixture was acidified by adding 1M 44 HCl, and then extracted with ethyl acetate (2×30 mL). The combined extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated. The residue was directly for the next step. LCMS (m/z): 171.0 (M+1).

Reference： [1]Patent: WO2014/100730,2014,A1 .Location in patent: Paragraph 00262
[2]Patent: US2019/83482,2019,A1 .Location in patent: Paragraph 0236-0237

20
[ 404-98-8 ]
[ 954279-15-3 ]
[ 1616074-73-7 ]

Yield	Reaction Conditions	Operation in experiment
5.6%	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25℃; for 16h;	To a stirred mixture of 54 <strong>[404-98-8]2-(3-fluorophenoxy)acetic acid</strong> (252 mg, 0.893 mmol) in 31 DCM (5 mL) was added 48 DIEA (173 mg, 1.34 mmol), 6 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (183 mg, 0.893 mmol), and Bop-C1 (273 mg, 1.07 mmol). The mixture was stirred at 25 C. for 16 hours then quenched with water (20 mL), extracted with DCM (3×20 mL). The combined extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was then purified by prep-HPLC to afford the 52 product (18 mg, Yield 5.6%). 1H NMR (400 MHz, METHANOL-d4) delta=7.26-7.29 (m, 1H), 7.13-7.02 (m, 4H), 6.76-6.69 (m, 3H), 4.55 (s, 2H), 4.06-4.00 (m, 1H), 3.71 (s, 1H), 3.47-3.31 (m, 2H), 2.91-2.90 (m, 2H), 2.86-2.77 (m, 2H), 2.61 (d, J=6.0 Hz, 2H). LCMS (m/z): 359.1 (M+1).
18 mg	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25℃; for 16h;	To a stirred mixture of <strong>[404-98-8]2-(3-fluorophenoxy)acetic acid</strong> (252mg, 0.893mmol) in DCM (5 mL) was added DIEA (173 mg ,1.34 mmol), l-amino-3-(3,4-dihydroisoquinolin- 2(lH)-yl)propan-2-ol (183 mg, 0.893 mmol), and Bop-Cl (273 mg, 1.07 mmol). The mixture was stirred at 25 C for 16 hours then quenched with water (20 mL), extracted with DCM (3x20 mL). The combined extracts were washed with brine (20 mL), dried over anhydrous Na2S04 and concentrated. The residue was then purified by prep-HPLC to afford the product (18 mg, Yield 5.6%). 1H NMR (400MHz, METHANOL-d ) delta = 7.26 - 7.29 (m, 1H), 7.13 - 7.02 (m, 4H), 6.76 - 6.69 (m, 3H), 4.55 (s, 2H), 4.06 - 4.00 (m, 1H), 3.71 (s, 1H), 3.47 - 3.31 (m, 2H), 2.91 - 2.90 (m, 2H), 2.86 - 2.77 (m, 2H), 2.61 (d, J=6.0 Hz, 2H). LCMS (m/z): 359.1(M+1).

Reference： [1]Patent: US2019/83482,2019,A1 .Location in patent: Paragraph 0238-0239
[2]Patent: WO2014/100730,2014,A1 .Location in patent: Paragraph 00263

21
[ 404-98-8 ]
O,O-dimethyl 1-[(3-fluorophenoxy)acetoxy]-1-(pyridin-2-yl)methylphosphonate [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 173 - 179

22
[ 372-20-3 ]
[ 96-32-2 ]
[ 404-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h;	General procedure: To a solution of phenols (50 mmol) in DMF (80 mL) was added potassium carbonate(10.4 g, 75 mmol) and methyl bromoacetate (5.7 mL, 60mmol). After stirring at room temperature for 12 h, the solution was dilutedwith ethyl acetate (200 mL) and washed with brine, dried over anhydrous sodiumsulfate, filtered and concentrated under vacuum to afford the productas awhite solid.