[ CAS No. 68886-07-7 ]

Name: 68886-07-7|2-Fluoro-4-hydroxyphenylacetic acid|95%
Brand: Ambeed
SKU: A212604
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Quality Control of [ 68886-07-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 68886-07-7 ]

SDS Specification

Alternatived Products of [ 68886-07-7 ]

Product Details of [ 68886-07-7 ]

CAS No. :	68886-07-7	MDL No. :	MFCD09027748
Formula :	C₈H₇FO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YBHJEGWOCHZSGY-UHFFFAOYSA-N
M.W :	170.14	Pubchem ID :	19361977
Synonyms :

Calculated chemistry of [ 68886-07-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	39.97
TPSA :	57.53 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) :	-6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.02
Log Po/w (XLOGP3) :	1.13
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	1.49
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.43 mg/ml ; 0.0143 mol/l
Class :	Very soluble
Log S (Ali) :	-1.93
Solubility :	1.99 mg/ml ; 0.0117 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.87
Solubility :	2.27 mg/ml ; 0.0134 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 68886-07-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 68886-07-7 ]

* 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.

Upstream synthesis route of [ 68886-07-7 ]
Downstream synthetic route of [ 68886-07-7 ]

[ 68886-07-7 ] Synthesis Path-Upstream 1~6

1
[ 883531-28-0 ]
[ 68886-07-7 ]

Reference： [1] Patent: WO2010/4347, 2010, A1, . Location in patent: Page/Page column 30

2
[ 78989-55-6 ]
[ 68886-07-7 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 237, p. 399 - 406

3
[ 372-20-3 ]
[ 68886-07-7 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 237, p. 399 - 406

4
[ 1042702-57-7 ]
[ 68886-07-7 ]

Reference： [1] Canadian Journal of Chemistry, 2011, vol. 89, # 3, p. 364 - 384

5
[ 68886-07-7 ]
[ 18107-18-1 ]
[ 91361-59-0 ]

Reference： [1] Patent: WO2010/4347, 2010, A1, . Location in patent: Page/Page column 30

6
[ 67-56-1 ]
[ 68886-07-7 ]
[ 91361-59-0 ]

Reference： [1] Patent: WO2012/138845, 2012, A1, . Location in patent: Page/Page column 45-46
[2] Patent: WO2013/74388, 2013, A1, . Location in patent: Page/Page column 68

[ 68886-07-7 ] Synthesis Path-Downstream 1~63

1
[ 68-12-2 ]
[ 68886-07-7 ]
(Z)-3-Dimethylamino-2-(2-fluoro-4-hydroxy-phenyl)-propenal [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 399 - 406

2
[ 78989-55-6 ]
[ 68886-07-7 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 399 - 406

3
[ 372-20-3 ]
[ 68886-07-7 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 399 - 406

4
[ 68886-07-7 ]
3-Fluoro-4-[2-(4-octyloxy-phenyl)-pyrimidin-5-yl]-phenol [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 399 - 406

5
[ 68886-07-7 ]
(R)-5-<4-<1-(Ethoxycarbonyl)ethoxy>-2-(fluoro)phenyl>-2-<4-(n-octyloxy)phenyl>pyrimidine [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 399 - 406

6
[ 68886-07-7 ]
(S)-5-<4-<1-(Ethoxycarbonyl)ethoxy>-2-(fluoro)phenyl>-2-<4-(n-octyloxy)phenyl>pyrimidine [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 399 - 406

7
[ 68886-07-7 ]
[ 821765-65-5 ]

Yield	Reaction Conditions	Operation in experiment
		Borane-tetrahydrofuran complex (1.0 M solution in THF, 22 ml, 0.02200 mol) was added dropwise to the solution of (2-fluoro-4-hydroxyphenyl) acetic acid (P. C. Belanger et al. EP 106565 B 1, 2.27 g, 0.01145 mol) in dry THF (40 ml) under nitrogen AT-10 C, and the resulting solution was stirred for 2 h AT-10 C. Water was added and the product was extracted into ethyl acetate. The combined extracts were washed with water, dried and evaporated in vacuo to give the product NMR (400 MHz, DMSO-d6) : 2.62 (2H, T, = 7.2 Hz), 3.50 (2H, M), 4.63 (1H, t, 3J = 5.4 Hz, - CH20H), 6.47-6. 53 (2H, M), 7.06 (1H, t, 3JHH = 4JHF = 8.5 Hz), 9.60 (1H, s, ArOH).

Reference： [1]Patent: WO2005/794,2005,A1 .Location in patent: Page 58; 59

8
[ 824-94-2 ]
[ 68886-07-7 ]
[ 908093-98-1 ]
[ 68886-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; potassium carbonate; In hexane; dichloromethane; acetic acid; acetone;	Preparation 1 To a solution of <strong>[68886-07-7]4-hydroxy-2-fluorophenylacetic acid</strong> in methylene chloride is added dropwise a solution of diphenyldiazomethane in n-hexane. A small amount of glacial acetic acid is added thereto. The mixture is concentrated to give the corresponding diphenylmethyl ester. The product is dissolved in acetone, and 1.3 equivalents of p-methoxybenzyl chloride, 1.2 equivalents of sodium iodide and 1.2 equivalents of potassium carbonate are added thereto. The mixture is stirred at 50 C. for 12 hours and, after removal of inorganic compounds, is extracted with ethyl acetate. The extract is concentrated and the residue is crystallized from methanol to give diphenylmethyl 4-p-methoxybenzyloxy-2-fluorophenylacetate.

Reference： [1]Patent: US4183928,1980,A

9
[ 68886-07-7 ]
[ 18107-18-1 ]
[ 91361-59-0 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of (2-fluoro-4-methoxyphenyl)acetic acid (4.50 g, 24.4 mmol) and aqueous hydrobromic acid (48%, 60 mL) was stirred under reflux for 12 h. The solvent was removed in vacuo and the residue was co-evaporated with MeOH several times, before being taken up in PhMe (200 mL) and MeOH (50 mL). The mixture was cooled to O0C, before being treated with (trimethylsilyl)diazomethane (13 mL, 2 M solution in hexane). The reaction was stirred from O0C to ambient temperature over 1 h, then quenched with AcOH (10 mL) and concentrated in vacuo. Purification by column chromatography (IH-EtOAc, 2:1) afforded the title compound: RT = 2.68 min; mlz (ES+) = 248.06 [M + CH3CN + Na]+ (Method A).

Reference： [1]Patent: WO2010/4347,2010,A1 .Location in patent: Page/Page column 30

10
[ 883531-28-0 ]
[ 68886-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; In water; for 2.5h;Reflux;	A mixture of <strong>[883531-28-0](2-fluoro-4-methoxyphenyl)acetic acid</strong> (4.50 g, 24.4 mmol) and aqueous hydrobromic acid (48%, 60 mL) was stirred under reflux for 12 h. The solvent was removed in vacuo and the residue was co-evaporated with MeOH several times, before being taken up in PhMe (200 mL) and MeOH (50 mL). The mixture was cooled to O0C, before being treated with (trimethylsilyl)diazomethane (13 mL, 2 M solution in hexane). The reaction was stirred from O0C to ambient temperature over 1 h, then quenched with AcOH (10 mL) and concentrated in vacuo. Purification by column chromatography (IH-EtOAc, 2:1) afforded the title compound: RT = 2.68 min; mlz (ES+) = 248.06 [M + CH3CN + Na]+ (Method A).

Reference： [1]Patent: WO2010/4347,2010,A1 .Location in patent: Page/Page column 30

11
[ 1042702-57-7 ]
[ 68886-07-7 ]

Reference： [1]Canadian Journal of Chemistry,2011,vol. 89,p. 364 - 384

12
[ 68886-07-7 ]
[ 1402555-11-6 ]

Reference： [1]Patent: WO2012/138845,2012,A1

13
[ 68886-07-7 ]
[ 1402555-12-7 ]

Reference： [1]Patent: WO2012/138845,2012,A1

14
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[ 1402555-23-0 ]

Reference： [1]Patent: WO2012/138845,2012,A1

15
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[ 1402555-24-1 ]

Reference： [1]Patent: WO2012/138845,2012,A1

16
[ 68886-07-7 ]
[ 1402555-27-4 ]

Reference： [1]Patent: WO2012/138845,2012,A1

17
[ 68886-07-7 ]
[ 1402555-28-5 ]

Reference： [1]Patent: WO2012/138845,2012,A1

18
[ 68886-07-7 ]
[ 1402555-40-1 ]

Reference： [1]Patent: WO2012/138845,2012,A1

19
[ 68886-07-7 ]
[ 1402555-41-2 ]

Reference： [1]Patent: WO2012/138845,2012,A1

20
[ 68886-07-7 ]
[ 1402554-43-1 ]

Reference： [1]Patent: WO2012/138845,2012,A1

21
[ 68886-07-7 ]
[ 1402555-42-3 ]

Reference： [1]Patent: WO2012/138845,2012,A1

22
[ 68886-07-7 ]
[ 1402554-44-2 ]

Reference： [1]Patent: WO2012/138845,2012,A1

23
[ 68886-07-7 ]
2-[2-fluoro-4-(2-{(1S,2R)-2-[1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetohydrazide [ No CAS ]

Reference： [1]Patent: WO2012/138845,2012,A1

24
[ 67-56-1 ]
[ 68886-07-7 ]
[ 91361-59-0 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid;	Intermediate 7:Preparation of methyl (2-fluoro-4-hydroxyphenyl) acetate: To a solution of <strong>[68886-07-7](2-fluoro-4-hydroxylphenyl) acetic acid</strong> (10 g, 58.8 mmol) in 400 ml methanol was added sulfuric acid (15.7 ml, 294 mmol). The reaction was refluxed overnight. The mixture was concentrated, and diluted with water, adjusted pH~7 with IN NaOH, and extracted with EtOAC (3X 250 ml), washed with brine and the organics were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified on Biotage column (100 g silica gel ) using a gradient eluent of 10-100% ethyl acetate in hexanes (2500 ml) to afford the title compound. LC/MS (m/z) 185.2 (M+H)+.
	With sulfuric acid;Reflux;	To a solution of (2-fluoro-4-hoxylphenyl) acetic acid (10 g, 58.8 mmol) in 400 ml methanol was added sulfuric acid (15.7 ml, 294 mmol). The reaction mixture was refluxed overnight. The mixture was concentrated under reduced pressure, diluted with water, adjusted pH~7 with IN NaOH, extracted with EtOAc (3X 250 ml), washed with brine, the organic layers combined, dried over magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (100 g silica gel) using a gradient eluent of 10-100% ethyl acetate in hexanes (2500 ml) to afford the title compound. LC/MS (m/z) 185.2 (M+H)+.

Reference： [1]Patent: WO2012/138845,2012,A1 .Location in patent: Page/Page column 45-46
[2]Patent: WO2013/74388,2013,A1 .Location in patent: Page/Page column 68

25
[ 68886-07-7 ]
[ 1437778-91-0 ]