22717-55-1|Methyl 4-chloro-2-hydroxybenzoate| Ambeed

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Quality Control of [ 22717-55-1 ] Purity: 97% SDS Specification

COA

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Product Details of [ 22717-55-1 ]

CAS No. :	22717-55-1
Formula :	C₈H₇ClO₃
M.W :	186.59
SMILES Code :	O=C(OC)C1=CC=C(Cl)C=C1O
MDL No. :	MFCD03407436
Boiling Point :	No data available
InChI Key :	QXDWMJQRXWLSDP-UHFFFAOYSA-N
Pubchem ID :	327085

Safety of [ 22717-55-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 22717-55-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	44.75
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.97
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	3.63
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.83
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.	1.91
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	1.85
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.52
Solubility	0.0561 mg/ml ; 0.000301 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.	-4.3
Solubility	0.00946 mg/ml ; 0.0000507 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-2.52
Solubility	0.569 mg/ml ; 0.00305 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	No
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.	-4.86 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<2.0
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)	1.42

Application In Synthesis of [ 22717-55-1 ]

* 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 [ 22717-55-1 ]

[ 22717-55-1 ] Synthesis Path-Downstream 1~35

1
[ 358-23-6 ]
[ 22717-55-1 ]
[ 212892-02-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In dichloromethane; at -25 - 20℃;Inert atmosphere;	Compound 4 was dissolved in DCM (100 mL), and the solution cooled to -25 C and stirred under N2 atmosphere. After 5 minutes, TEA (2 eq) was added, followed by dropwise addition of trifluoromethanesulfonic (triflic) anhydride (Tf2O, 1.5 eq). The mixture was stirred at -25 C for 30 minutes, then warmed to room temperature, and diluted with Et2O (100 mL) and washed with 1 M aq. HCl (3 × 50 mL) and saturated aq. NaCl (1 × 50 mL). The organic layer was collected, dried over anhydrous Na2SO4 and evaporated to dryness under reduced pressure, affording 5 as a colourless oil (67% yield).
	With triethylamine; In dichloromethane; at -78 - 20℃;	To a round bottom flask was dissolved <strong>[22717-55-1]methyl-4-chloro-2-hydroxybenzoate</strong> (100g, 537mmol) in methylene chloride 1000mL put Triethylamine (113mL, 805mmol). It was added dropwise trifluoromethanesulfonic anhydride (99mL, 590mmol) at -78 C and then raise the temperature gradually to room temperature. After the reaction is extracted with water, filtered, the organic layer over MgSO4, remove water. Remove the organic solvent and then to remove the dark color after separation silicagel column dissolved in ether and the solvent and vacuum drying.

References: [1]Tetrahedron Letters,2019,vol. 60,p. 1166 - 1169.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343.
[3]Patent: KR2015/31892,2015,A .Location in patent: Paragraph 0269; 0272-0273.

2
[ 5106-98-9 ]
[ 74-88-4 ]
[ 22717-55-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1.5h;	Cs2CO3 (0.5 eq) was added to a solution of 4-chloro-2-hydroxybenzoic acid (4-chlorosalycilic acid, 3) in DMF (200 mL), followed by addition, after 5 minutes, of iodomethane (5 equiv). The solution was stirred for 1.5 h, then diluted with diethyl ether/ethyl acetate (Et2O/EtOAc, 2:1 v/v) (100 mL), and washed with saturated aq. NaHCO3 (3 × 50 mL), then with saturated aq. NaCl (1 × 50 mL). The organic layer was collected, dried over anhydrous Na2SO4 and evaporated to dryness under reduced pressure, affording 4 as a colourless oil (quantitative).
92%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step-I: Methyl 4-chloro-2-hydroxy-benzoate (VII-l-I): To a solution of 4-chlorosalicylic acid (75 g, 435.6 mmol) in anhydrous DMF (871 mL) was added Cs2C03 (70.7 g, 217.8 mmol) and Mel (27.5 mL, 439.9 mmol) sequentially. The reaction mixture was stirred at room temperature overnight. Ice cold water (3 L) was added to the reaction mixture and the precipitated solid was filtered and dried to provide VII- 1 -I (75 g, 92% yield).
92%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step-I: Methyl 4-chloro-2-hydroxy-benzoate (VII-1-I) To a solution of 4-chlorosalicylic acid (75 g, 435.6 mmol) in anhydrous DMF (871 mL) was added Cs2CO3 (70.7 g, 217.8 mmol) and MeI (27.5 mL, 439.9 mmol) sequentially. The reaction mixture was stirred at room temperature overnight. Ice cold water (3 L) was added to the reaction mixture and the precipitated solid was filtered and dried to provide VII-1-I (75 g, 92% yield).

92%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step-I: Methyl 4-chloro-2-hydroxy-benzoate (VII-1-I): To a solution of 4-chlorosalicylic acid (75 g, 435.6 mmol) in anhydrous DMF (871 mL) was added Cs2CO3 (70.7 g, 217.8 mmol) and MeI (27.5 mL, 439.9 mmol) sequentially. The reaction mixture was stirred at room temperature overnight. Ice cold water (3 L) was added to the reaction mixture and the precipitated solid was filtered and dried to provide VII-1-I (75 g, 92% yield).
64.93%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	To a stirred solution of 4-chloro-2-hydroxybenzoic acid (5.0 g, 28.968 mmol, 1.0 eq)in DMF (60 mL) was added Cs2C03 (4.719 g, 14.484 mmol, 0.5 eq) and methyl iodide (4.52g, 31.864 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for overnight.After completion of the reaction (monitored by TLC), the reaction mixture was diluted withwater (600 mL) and extracted with ethyl acetate (2xl00 mL). The combined organic extracts25 were washed with water (2x200 mL), dried over Na2S04, filtered and evaporated underreduced pressure to obtain the title compound (3.5 g, yield: 64.93%) as a liquid. 1H NMR(300 MHz, CDCh): 8 ppm 10.86 (s, IH), 7.77 (d, J = 8.7 Hz, IH), 7.01 (d, J = 2.1 Hz, IH),6.87 (dd, J = 8.7, 2.1 Hz, IH), 3.96 (s, 3H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4.5h;	Into the 4-chloro-2-hydroxybenzoic acid (200g, 1159mmol) and potassium carbonate (80g, 579mmol) and DMF 1000mL round bottom flask and stirred. If the mixture is melted and added dropwise methyl iodide (172g, 1217mmol) at room temperature for 4.5 hours after the end the reaction at room temperature. Ether extraction with water and then removing the water and the organic layer over MgSO4 and silica gel filter. The filtered organic layer is evaporated and dried under vacuum.

References: [1]Tetrahedron Letters,2019,vol. 60,p. 1166 - 1169.
[2]Patent: WO2013/157022,2013,A1 .Location in patent: Page/Page column 42-43.
[3]Patent: US2015/64196,2015,A1 .Location in patent: Paragraph 0128.
[4]Patent: EP3042903,2016,A1 .Location in patent: Paragraph 0115; 0116.
[5]Patent: WO2018/29604,2018,A1 .Location in patent: Page/Page column 53.
[6]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343.
[7]Patent: KR2015/31892,2015,A .Location in patent: Paragraph 0268-0271.

3
[ 22717-55-1 ]
[ 64917-81-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

4
[ 22717-55-1 ]
[ 65920-15-2 ]

References: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 5046 - 5054.

5
[ 22717-55-1 ]
[ 226888-37-5 ]
[ 949570-69-8 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4162 - 4176.

6
[ 22717-55-1 ]
[ 905303-91-5 ]

References: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 5046 - 5054.

7
[ 22717-55-1 ]
[ 905303-89-1 ]

References: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 5046 - 5054.

8
[ 22717-55-1 ]
[ 905303-90-4 ]

References: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 5046 - 5054.

9
[ 22717-55-1 ]
[ 905303-92-6 ]

References: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 5046 - 5054.

10
[ 22717-55-1 ]
[ 25546-09-2 ]

References: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 5046 - 5054.

11
[ 22717-55-1 ]
[ 907587-62-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

12
[ 22717-55-1 ]
[ 907587-65-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

13
[ 22717-55-1 ]
[ 907587-64-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

14
[ 22717-55-1 ]
4-(5-chloro-2-phenoxymethyl-phenoxymethyl)-benzoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

15
[ 22717-55-1 ]
[ 907587-66-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

16
[ 22717-55-1 ]
[ 907587-63-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

17
[ 22717-55-1 ]
[ 874813-50-0 ]