[ CAS No. 123843-65-2 ] {[proInfo.proName]}

Name: 123843-65-2|2,6-Difluoro-4-methoxybenzoic acid|95%
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SKU: A222453
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Quality Control of [ 123843-65-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 123843-65-2 ]

Product Details of [ 123843-65-2 ]

CAS No. :	123843-65-2	MDL No. :	MFCD02949623
Formula :	C₈H₆F₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LGHVYSAINQRZJQ-UHFFFAOYSA-N
M.W :	188.13	Pubchem ID :	2778228
Synonyms :

Calculated chemistry of [ 123843-65-2 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.81
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) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	1.62
Log Po/w (WLOGP) :	2.51
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	2.08
Consensus Log Po/w :	1.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	1.09 mg/ml ; 0.0058 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	1.16 mg/ml ; 0.00617 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.46
Solubility :	0.654 mg/ml ; 0.00348 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 123843-65-2 ]

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 [ 123843-65-2 ]

* 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 [ 123843-65-2 ]
Downstream synthetic route of [ 123843-65-2 ]

[ 123843-65-2 ] Synthesis Path-Upstream 1~8

1
[ 123843-65-2 ]
[ 93343-10-3 ]

Reference： [1] Organic Letters, 2010, vol. 12, # 5, p. 992 - 995

2
[ 123843-65-2 ]
[ 151414-47-0 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 1, p. 95 - 98

3
[ 123843-65-2 ]
[ 84937-82-6 ]

Reference： [1] Patent: US6149990, 2000, A,

4
[ 123843-65-2 ]
[ 123843-57-2 ]

Reference： [1] Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 172, p. 165 - 190

5
[ 124-38-9 ]
[ 93343-10-3 ]
[ 123843-65-2 ]

Yield	Reaction Conditions	Operation in experiment
5.00 g	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere Stage #2: With silica gel In tetrahydrofuran; hexane at -78 - 35℃; for 0.0833333 h;	Under a nitrogen atmosphere, a 1.6 M solution of n-butyllithium in hexane (31.2 mL) was added to a solution of 1,3-difluoro-5-methoxybenzene (5.54 g) in THF (120 mL) at −78° C., and the mixture was stirred at −78° C. for 30 min. Sublimated dry ice (8.46 g) was added to the reaction solution through a silica gel tube at −78° C., and the mixture was stirred at room temperature for 5 min. To the reaction solution was added 1N hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained solid was washed with hexane and diisopropyl ether to give the title compound (5.00 g) as a white solid. (1338) ¹H NMR (400 MHz, DMSO-d₆) δ 3.83 (3H, s), 6.82 (2H, d, J=11.0 Hz), 13.43 (1H, brs).

Reference： [1] Heterocycles, 2006, vol. 67, # 2, p. 489 - 494
[2] Tetrahedron Letters, 2004, vol. 45, # 1, p. 95 - 98
[3] Patent: US2016/115128, 2016, A1, . Location in patent: Paragraph 1337; 1338

6
[ 123843-66-3 ]
[ 123843-65-2 ]

Reference： [1] Patent: US5156763, 1992, A,

7
[ 93343-10-3 ]
[ 123843-65-2 ]

Reference： [1] Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 172, p. 165 - 190
[2] Patent: US6149990, 2000, A,

8
[ 2713-34-0 ]
[ 123843-65-2 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 1, p. 95 - 98

[ 123843-65-2 ] Synthesis Path-Downstream 1~88

1
[ 93343-10-3 ]
[ 123843-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;	2) To THF (200 ml) was dissolved 3,5-difluoroanisol (134 g) and then 1.64 M of n-butyllithium/hexane (568 ml) was added and stirred for 1 hour. The mixture formed was added to a solution of dryice (9.4 g) dissolved in THF (100 ml), and was stirred at room temperature for 2 hours. After the reaction, the mixture was added with diluted hydrochloric acid (700 ml) and extracted with ethyl acetate (700 ml). The organic layer separated was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to give 2,6-difluoro-4-methoxybenzoic acid (102 g).

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1989,vol. 172,p. 165 - 190
[2]Patent: US6149990,2000,A

2
[ 123843-65-2 ]
[ 125369-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 50℃; for 3h;	To a mixture of <strong>[123843-65-2]2,6-difluoro-4-methoxybenzoic acid</strong> (2.0 g, 10.6 mmol) in dichloromethane (30 mL) were added oxalyl chloride (1.49 g, 1 1.7 mmol) and A,N-dimethylformamide (1 drop). The reaction mixture was heated at 50 C for 3 h, cooled to room temperature and concentrated under reduced pressure to provide the title compound as an oil (2.0 g).
	With thionyl chloride; In N,N-dimethyl-formamide; for 3h;Reflux;	3 hours under reflux to a stirred solution of <strong>[123843-65-2]2,6-difluoro-4-methoxybenzoic acid</strong> in thionyl chloride (7ml) (0.25g, 1.34mmol), was added a drop of DMF, then the reaction mixture heated. After cooling to room temperature, the excess reagent was removed under reduced pressure to give the crude residue. Sections of this crude residue and 4- (6-methyl-imidazo [1,2-a] pyridin-2-yl) aniline (0.30 g, 1.34 mmol) and amide coupling using in dry pyridine (15 ml) the amide prepared as described in, work-up and flash chromatography (2: 1 EtOAc / hexanes, then EtOAc, then MeOH) later, the title compound (0.24g, 45%) as a pale yellow solid Obtained

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1989,vol. 172,p. 165 - 190
[2]Tetrahedron Letters,2004,vol. 45,p. 95 - 98
[3]Patent: WO2011/51958,2011,A1 .Location in patent: Page/Page column 36
[4]Journal of Medicinal Chemistry,2013,vol. 56,p. 7084 - 7099
[5]Patent: JP5667058,2015,B2 .Location in patent: Paragraph 0753

3
[ 64-17-5 ]
[ 123843-65-2 ]
(2,6-difluoro-4-methoxyphenyl)carbamic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 95 - 98

4
[ 124-38-9 ]
[ 93343-10-3 ]
[ 123843-65-2 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a solution of 1, 3-difluoro-5-methoxybenzene (40.0 g, 277.7 mmol) in THF (250 mL) was added n-BuLi (120 mL, 361.1 mmol) dropwise at -78 with N 2 protected. After addition, the resulting mixture was stirred for 1 h at -78 . Then dry ice (61 g, 1.39 mol) was added and the reaction mixture was allowed to room temperature and stirred for 10 min. Then the reaction mixture was added 1 N HCl at 0 and extracted with EA/THF (200 mL x3) . The combined organic layers were dried over anhydrous Na 2SO 4, filtered and concentrated to give crude product. The crude product was triturated in PE/EA=25: 1 and filtered to give product (40 g, 77%yield) as off-white solid. 1H NMR (400 MHz, DMSO-d 6) : delta 13.42 (brs, 1H) , 8.85 (s, 1H) , 8.80 (s, 1H) , 3.80 (s, 3H) .v
5.00 g		Under a nitrogen atmosphere, a 1.6 M solution of n-butyllithium in hexane (31.2 mL) was added to a solution of 1,3-difluoro-5-methoxybenzene (5.54 g) in THF (120 mL) at -78 C., and the mixture was stirred at -78 C. for 30 min. Sublimated dry ice (8.46 g) was added to the reaction solution through a silica gel tube at -78 C., and the mixture was stirred at room temperature for 5 min. To the reaction solution was added 1N hydrochloric acid at 0 C., and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained solid was washed with hexane and diisopropyl ether to give the title compound (5.00 g) as a white solid. (1338) 1H NMR (400 MHz, DMSO-d6) delta 3.83 (3H, s), 6.82 (2H, d, J=11.0 Hz), 13.43 (1H, brs).

Reference： [1]Heterocycles,2006,vol. 67,p. 489 - 494
[2]Tetrahedron Letters,2004,vol. 45,p. 95 - 98
[3]Patent: WO2020/57511,2020,A1 .Location in patent: Page/Page column 176-177
[4]Patent: US2016/115128,2016,A1 .Location in patent: Paragraph 1337; 1338

5
[ 123843-65-2 ]
[ 125369-57-5 ]

Yield	Reaction Conditions	Operation in experiment
72%		To a solution of 2, 6-difluoro-4-methoxybenzoic acid (45.0 g, 240 mmol) in CH 2Cl 2 (120mL) was added DMF (0.1 mL) and oxalyl chloride (50 mL, 840 mmol) dropwise. The reaction mixture was stirred for 30 min and then concentrated to give a residue. The residue was dissolved in DCM (120 mL) and then was added into a mixture of NH 4OH/THF (200mL/200mL) slowly. After addition the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, re-dissolved in water and extracted with DCM (300 mLx3) . The combined organic phases were washed with brine, dried over anhydrous Na 2SO 4 and filtered. The filtrate was concentrated. The residue was triturated in PE/EA (20: 1, 500 mL) and filtered to give the product (32 g, 72%yield) as a yellow solid. MS (ESI) m/z: 188.2 (M+H) +.

Reference： [1]Patent: WO2020/57511,2020,A1 .Location in patent: Page/Page column 176-177
[2]Heterocycles,2006,vol. 67,p. 489 - 494
[3]Molecular Crystals and Liquid Crystals (1969-1991),1989,vol. 172,p. 165 - 190

6
[ 123843-65-2 ]
[ 601517-02-6 ]