[ CAS No. 22717-55-1 ] Methyl 4-chloro-2-hydroxybenzoate

Cat. No.: A274340

2D 3D

Structure of 22717-55-1 * Storage: Inert atmosphere,Room Temperature

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* Storage: Inert atmosphere,Room Temperature

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Quality Control of [ 22717-55-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22717-55-1 ]

Specification

Alternatived Products of [ 22717-55-1 ]

Product Details of [ 22717-55-1 ]

CAS No. :	22717-55-1	MDL No. :	MFCD03407436
Formula :	C₈H₇ClO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QXDWMJQRXWLSDP-UHFFFAOYSA-N
M.W :	186.59	Pubchem ID :	327085
Synonyms :

Calculated chemistry of [ 22717-55-1 ] Expand+

Safety of [ 22717-55-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

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 1~23

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.

Reference： [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.

Reference： [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 ]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Reference： [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 ]

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

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

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

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

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

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

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

18
[ 22717-55-1 ]
4-chloro-2-(3-fluoro-2-methyl-phenylamino)-benzoic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

19
[ 22717-55-1 ]
4-chloro-2-(3-fluoro-2-methyl-phenylamino)-benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

20
[ 22717-55-1 ]
3-chloro-5-methyl-9-phenoxy-acridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

21
[ 22717-55-1 ]
[ 874813-51-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

22
[ 22717-55-1 ]
4-chloro-2-(4-trifluoromethyl-phenylamino)-benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

23
[ 22717-55-1 ]
2-chloro-6-methoxy-9-phenoxy-acridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 334 - 343

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Technical Information

• Acidity of Phenols • Acyl Group Substitution • Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Electrophilic Substitution of the Phenol Aromatic Ring • Ester Cleavage • Etherification Reaction of Phenolic Hydroxyl Group • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Halogenation of Phenols • Hiyama Cross-Coupling Reaction • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reimer-Tiemann Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Vilsmeier-Haack Reaction

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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 :	46.53 Å²

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) :	-4.86 cm/s

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	3.63
Log Po/w (WLOGP) :	1.83
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	1.85
Consensus Log Po/w :	2.24

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

Log S (ESOL) :	-3.52
Solubility :	0.0561 mg/ml ; 0.000301 mol/l
Class :	Soluble
Log S (Ali) :	-4.3
Solubility :	0.00946 mg/ml ; 0.0000507 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.52
Solubility :	0.569 mg/ml ; 0.00305 mol/l
Class :	Soluble

[ CAS No. 22717-55-1 ] Methyl 4-chloro-2-hydroxybenzoate

Quality Control of [ 22717-55-1 ]

Related Doc. of [ 22717-55-1 ]

Product Details of [ 22717-55-1 ]

Calculated chemistry of [ 22717-55-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 22717-55-1 ]

Application In Synthesis of [ 22717-55-1 ]

[ 22717-55-1 ] Synthesis Path-Downstream 1~23

Technical Information