[ CAS No. 70163-98-3 ] {[proInfo.proName]}

Name: 70163-98-3|Methyl 3-fluoro-2-hydroxybenzoate|98%
Brand: Ambeed
SKU: A102667
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Quality Control of [ 70163-98-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 70163-98-3 ]

SDS Specification

Alternatived Products of [ 70163-98-3 ]

Product Details of [ 70163-98-3 ]

CAS No. :	70163-98-3	MDL No. :	MFCD06203651
Formula :	C₈H₇FO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NRGQRZHYRCJTKV-UHFFFAOYSA-N
M.W :	170.14	Pubchem ID :	573875
Synonyms :

Calculated chemistry of [ 70163-98-3 ]

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 :	1.0
Molar Refractivity :	39.7
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) :	-5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	2.65
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.75
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	1.95

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.8
Solubility :	0.268 mg/ml ; 0.00158 mol/l
Class :	Soluble
Log S (Ali) :	-3.28
Solubility :	0.0897 mg/ml ; 0.000527 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.17
Solubility :	1.14 mg/ml ; 0.00673 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 70163-98-3 ]

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 [ 70163-98-3 ]

* 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 [ 70163-98-3 ]
Downstream synthetic route of [ 70163-98-3 ]

[ 70163-98-3 ] Synthesis Path-Upstream 1~7

1
[ 119-36-8 ]
[ 391-92-4 ]
[ 70163-98-3 ]

Reference： [1] Journal of Organic Chemistry, 1984, vol. 49, p. 806 - 813
[2] Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4629 - 4631

2
[ 455-68-5 ]
[ 70163-98-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With oxone; Ru(MesCO₂)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride In 1,2-dichloro-ethane at 110℃; for 12 h; Sealed tube; Green chemistry	General procedure: The Ru(MesCO₂)(L) (p-cymene) [L- 2,2’-bypyridine or 4,4’-dibromobipyridine] (2.5 molpercent), oxidant (2.0 eq) and ester (1.0 eq) were added to a sealed tube. Following that, trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) in the ratio of 0.6 ml: 0.4 were added. The reaction mixture was kept on a pre-heated bath at 110°C and stirred until its completion. It was continuously monitored by TLC. Ice water was added to quench the reaction mixture and it was extracted with dichloromethane. The organic layer was dried over Na₂SO₄ and rota-evaporated. Finally the residue was purified by silica gel column chromatography to give corresponding products.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 38, p. 3743 - 3746

3
[ 67-56-1 ]
[ 341-27-5 ]
[ 70163-98-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	for 18 h; Heating / reflux	Concentrated sulphuric acid (6 ml) was added to 3-fluoro-2-hydroxybenzoic acid (103)(5 g, 32 mmol) in methanol (20 ml). This was left to stir at reflux 18 hours. The reaction mixture was concentrated under vacuum, then saturated sodium bicarbonate (500 ml) was added and product extracted with EtOAc (3.x.150 ml). The organic extracts were collated, dried over MgSO₄, and evaporated to give compound 104 (3.9 g, yield: 72percent, [M-H]^-: 169) as liquid which solidified into pale yellow crystals.

Reference： [1] Patent: US2006/135770, 2006, A1, . Location in patent: Page/Page column 27-28
[2] Patent: WO2007/62370, 2007, A2, . Location in patent: Page/Page column 46

4
[ 341-27-5 ]
[ 70163-98-3 ]

Reference： [1] Patent: US4140769, 1979, A,

5
[ 119-36-8 ]
[ 391-92-4 ]
[ 70163-98-3 ]

Reference： [1] Journal of Organic Chemistry, 1984, vol. 49, p. 806 - 813
[2] Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4629 - 4631

6
[ 67-56-1 ]
[ 854914-89-9 ]
[ 70163-98-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 7, p. 963 - 964

7
[ 367-12-4 ]
[ 70163-98-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 7, p. 963 - 964
[2] Patent: US4140769, 1979, A,

[ 70163-98-3 ] Synthesis Path-Downstream 1~22

1
[ 119-36-8 ]
[ 391-92-4 ]
[ 70163-98-3 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 806 - 813
[2]Journal of Organic Chemistry,1981,vol. 46,p. 4629 - 4631

3
[ 67-56-1 ]
[ 854914-89-9 ]
[ 70163-98-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 963 - 964

4
[ 367-12-4 ]
[ 70163-98-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 963 - 964
[2]Patent: US4140769,1979,A

5
[ 67-56-1 ]
[ 341-27-5 ]
[ 70163-98-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	sulfuric acid; for 18.0h;Heating / reflux;	Concentrated sulphuric acid (6 ml) was added to 3-fluoro-2-hydroxybenzoic acid (103)(5 g, 32 mmol) in methanol (20 ml). This was left to stir at reflux 18 hours. The reaction mixture was concentrated under vacuum, then saturated sodium bicarbonate (500 ml) was added and product extracted with EtOAc (3×150 ml). The organic extracts were collated, dried over MgSO4, and evaporated to give compound 104 (3.9 g, yield: 72%, [M-H]-: 169) as liquid which solidified into pale yellow crystals.
	sulfuric acid; for 16.0h;Heating / reflux;	The hydroxy acid (10 g, 0.064 moles) was taken up in anhydrous methanol (215 ml_). To this was added catalytic amount of sulfuric acid and the reaction was reflux for 16 h. The reaction was concentrated and the crude product was taken into the next step without purification.

Reference： [1]Patent: US2006/135770,2006,A1 .Location in patent: Page/Page column 27-28
[2]Patent: WO2007/62370,2007,A2 .Location in patent: Page/Page column 46

6
[ 70163-98-3 ]
[ 100-36-7 ]
[ 70163-99-4 ]

Yield	Reaction Conditions	Operation in experiment
		A 5.10 gram portion of <strong>[70163-98-3]methyl-3-fluorosalicylate</strong> (0.03 mole) was refluxed with a 3.49 g portion of N,N-diethylethylenediamine (0.03 mole) for about four hours and evaporated in vacuo. The brown oil obtained was chromatographed on silica gel with ether and the desired product isolated as the hydrochloride, m.p. 108-110 C. Calcd. for C13 H20 FClN2 O2: C, 53.69; H, 6.93; N, 9.64 Found: C, 52.58; H, 6.71; N, 9.58.

Reference： [1]Patent: US4140769,1979,A

7
[ 341-27-5 ]
[ 70163-98-3 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride methanol complex; sodium hydrogencarbonate; In methanol;	A 15.6 g (0.10 mole) portion of 3-fluorosalicylic acid was dissolved in a 100 ml portion of absolute methanol. A 22 ml portion of borontrifluoride-methanol reagent (2 equivalents, 51% BF3) was added and the reaction allowed to reflux for about six hours. The reaction mixture was cooled and added carefully to a saturated solution of sodium bicarbonate. The resulting mixture was then extracted with ether, the ether layer dried over magnesium sulfate and evaporated in vacuo. The oil obtained was crystallized from methanol. The methyl-3-fluorosalicylate obtained had a melting point of 94-5 C.

Reference： [1]Patent: US4140769,1979,A

8
[ 70163-98-3 ]
[ 705949-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In methanol; at 110.0℃; for 16.0h;	The methyl ester was placed in pressure reaction vessel. To this was added 2N ammonia in methanol (125 ml_) and the reaction was heated to 11O0C for 16 h. The reaction was concentrated and taken up in dichloromethane. The undissolved material is filtered off. The reaction is concentrated and dissolved in large amount of methanol and was decolorized. _The methanol solution was partly concentrated upon-which~crystalline~solid~(pale~brown) was crashed out. The solid is filtered and used in the next step.

Reference： [1]Patent: WO2007/62370,2007,A2 .Location in patent: Page/Page column 46

9
[ 70163-98-3 ]
[ 177348-35-5 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3357 - 3359

10
[ 70163-98-3 ]
[ 173019-83-5 ]
[ 934753-37-4 ]

Yield	Reaction Conditions	Operation in experiment
49%	With potassium carbonate; potassium iodide; In acetone; for 2.5h;Reflux;	Example 64A Methyl 5-fluoro-2-[3-(4-trifluoromethylphenyl)prop-2-ynyloxy]benzoate 4.12 g (24.2 mmol) of <strong>[70163-98-3]methyl 3-fluorosalicylate</strong> [CAS 391-924] are dissolved in 100 ml of acetone, 10.0 g (72.6 mmol) of potassium carbonate, 6.02 g 36.3 mmol) of potassium iodide and 7.00 g (26.6 mmol) of 1-(3-bromoprop-1-ynyl)-4-trifluoromethylbenzene [Beilstein Record No. 7919066] are added, and the mixture is stirred under reflux for 2.5 h. The solvent is distilled out in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. The solvent is distilled out in vacuo, and the residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1?5:1). 4.63 g (13.1 mmol, 49% of theory) of the title compound are obtained. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 7.75 (2H, dAB), 7.65 (2H, dAB), 7.52-7.45 (2H, m), 7.37 (1H, dd), 5.17 (2H, s), 3.82 (3H, s).

Reference： [1]Patent: US2009/227640,2009,A1 .Location in patent: Page/Page column 50-51

11
[ 455-68-5 ]
[ 70163-98-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With oxone; Ru(MesCO2)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride; In 1,2-dichloro-ethane; at 110℃; for 12h;Sealed tube; Green chemistry;	General procedure: The Ru(MesCO2)(L) (p-cymene) [L- 2,2?-bypyridine or 4,4?-dibromobipyridine] (2.5 molpercent), oxidant (2.0 eq) and ester (1.0 eq) were added to a sealed tube. Following that, trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) in the ratio of 0.6 ml: 0.4 were added. The reaction mixture was kept on a pre-heated bath at 110°C and stirred until its completion. It was continuously monitored by TLC. Ice water was added to quench the reaction mixture and it was extracted with dichloromethane. The organic layer was dried over Na2SO4 and rota-evaporated. Finally the residue was purified by silica gel column chromatography to give corresponding products.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3743 - 3746

12
[ 70163-98-3 ]
methyl 3-fluoro-2-(3-hydroxyprop-1-yn-1-yl)benzoate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3034 - 3038

13
[ 70163-98-3 ]
(Z)-3-fluoro-2-(3-hydroxyprop-1-en-1-yl)benzoic acid [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3034 - 3038

14
[ 70163-98-3 ]
4-fluoro-3-vinylisobenzofuran-1(3H)-one [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3034 - 3038

15
[ 70163-98-3 ]
C₁₁H₁₁FO₃ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3034 - 3038

16
[ 37595-74-7 ]
[ 70163-98-3 ]
methyl 3-fluoro-2-(triflate)benzoate [ No CAS ]