126617-98-9|(2-(Methoxymethyl)phenyl)boronic acid| Ambeed

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Quality Control of [ 126617-98-9 ] Purity: 97% SDS Specification

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Product Details of [ 126617-98-9 ]

CAS No. :	126617-98-9
Formula :	C₈H₁₁BO₃
M.W :	165.98
SMILES Code :	C1=C(C(=CC=C1)COC)B(O)O
MDL No. :	MFCD03412110
InChI Key :	JHPPAFXQJZJGEP-UHFFFAOYSA-N
Pubchem ID :	3759408

Safety of [ 126617-98-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 126617-98-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	47.13
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.69 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	0.48
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.64
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.	0.06
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	-0.43
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.11

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.34
Solubility	7.53 mg/ml ; 0.0453 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.09
Solubility	13.4 mg/ml ; 0.0808 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-1.81
Solubility	2.56 mg/ml ; 0.0154 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	No
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.	-6.97 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	1.0 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<1.0
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)	1.88

Application In Synthesis of [ 126617-98-9 ]

* 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 [ 126617-98-9 ]

[ 126617-98-9 ] Synthesis Path-Downstream 1~35

1
[ 126617-98-9 ]
[ 137936-91-5 ]
[ 137936-92-6 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 4883 - 4884.

2
[ 126617-98-9 ]
[ 29176-55-4 ]
[ 126617-90-1 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 267 - 270.

3
[ 126617-98-9 ]
2-[2-(Ethoxy-phenyl-phosphinoylmethyl)-phenyl]-13H-1-aza-13a-azonia-indeno[1,2-c]phenanthrene [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 267 - 270.

4
[ 126617-98-9 ]
2,9-Bis-(2-bromomethyl-phenyl)-[1,10]phenanthroline; hydrobromide [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 267 - 270.

5
[ 872173-46-1 ]
[ 126617-98-9 ]
C₂₄H₂₉N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; triphenylphosphine;palladium diacetate; In propan-1-ol; water; toluene; at 80℃;	l-[4-Ainino-7-bromo-2-(ethoxymethyl)-lH-imidazo[4,5-c][l,5]naphthyridin-l-yl]- 2-methylpropan-2-ol (0.039 g, 0.10 mmol) was added to a test tube. The boronic acid (0.11 mmol) indicated in the table below and n-propanol (1.6 niL) were sequentially added. The test tube was purged with nitrogen. Palladium (II) acetate (0.150 mL of a 4 rng/mL solution in toluene, 0.0026 mmol), 2 M aqueous sodium carbonate solution (0.600 rnL), deionized water (113 muL), and a solution of 0.15 mol% triphenylphosphine in n- propanol (53 muL, 0.0078 mmol) were sequentially added. The test tube was purged with nitrogen, capped, and then heated at 80 0C overnight.The contents of each test tube were passed through a Waters Oasis Sample Extractions Cartridge MCX (6 cc) according to the procedure described in Examples 4 - 58. The resulting basic solutions were concentrated by vacuum centrifugation. Each sample was subjected to the reaction with boron tribromide described in Examples 128 - 151 using 0.400 mL of boron tribromide solution for each test tube. Each reaction was stirred for six hours at room temperature. After methanol and 6 Nu hydrochloric acid were added to each tube, the contents were vortexed for 30 minutes, and the volatiles were removed by vacuum centrifugation. The compounds were purified by reversed phase prep HPLC according to the method described in Examples 77 - 127. The table below shows the reagent added to each test tube, the structure of the resulting compound, and the observed accurate mass for the isolated trifluoroacetate salt.

References: [1]Patent: WO2006/38923,2006,A2 .Location in patent: Page/Page column 161 - 163.

6
[ 619-58-9 ]
[ 126617-98-9 ]
2'-methoxymethyl-biphenyl-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); at 90℃; for 19h;	Example 61 10-[2'-(METHOXYMETHYL)-1,1'-BIPHENYL-4-YL]CARBONYL}-N-(PYRIDIN-3-YLMETHYL)-10,11-DIHYDRO-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-3-CARBOXAMIDE Step A. 2'-Methoxymethyl-biphenyl-4-carboxylic acid; To a suspension of 4-iodobenzoic acid (0.82 g, 3.31 mmol) and <strong>[126617-98-9]2-methoxymethylphenylboronic acid</strong> (0.55 g, 3.31 mmol) in dry acetonitrile (30 mL) was added a 0.4 M aqueous sodium carbonate solution (30 mL) and the reaction mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.078 mmol) was then added and the reaction mixture heated to 90 C. for 19 hours. The hot reaction mixture was filtered through celite, concentrated in vacuo to remove acetonitrile and the resulting aqueous suspension washed with ethyl acetate (2×30 mL). The aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid, the resulting white suspension cooled to 4 C. for 1 hour and the solid product filtered. Recrystallization from dichloroethane gave the title compound (0.469 g, 59%) as a white solid, m.p. 164.5-165.5 C. MS [(-)ESI, m/z]: 241 [M-H]-

References: [1]Patent: US2006/287522,2006,A1 .Location in patent: Page/Page column 40-41.

7
[ 890051-43-1 ]
[ 126617-98-9 ]
3-(2'-methoxymethyl-biphenyl-4-yloxymethyl)-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of intermediate 1; 37 mg, 0.1 mmol) in dioxane (2 mL) was degassed with nitrogen and then added to a reaction vial containing <strong>[126617-98-9]2-methoxymethylphenylboronic acid</strong> (available from Apollo Scientific Ltd., Stockport, UK). The solution was sonicated and degassed and a solution of sodium hydroxide (4 M, 0.2 mL) was added, followed by bis(tri-cyclo-hexylphosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 0.005 mmol) was added. The mixture was degassed and then heated in a microwave oven at 170 degrees for 25 min. The reaction mixture was filtered through silica and the silica washed with dioxane (1 mL), and dimethylacetamide (1 mL). 1 M HCl was added until a solid formed. The vial was centrifuged and the solvent was removed. The crude product was washed with water and centrifuged again for 5 min. The water was decanted and the solid was dried in a vacuum oven at 50 degrees to give 3-(2'-methoxymethyl-biphenyl-4-yloxymethyl)-benzoic acid. Mass spectrum MH+=349.

References: [1]Patent: US2006/122256,2006,A1 .Location in patent: Page/Page column 29.

8
[ 890051-46-4 ]
[ 126617-98-9 ]
[3-(2'-Methoxymethyl-biphenyl-4-yloxymethyl)-phenyl]-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General Procedure 4 for the Preparation of 3-Biaryloxymethyl-phenylacetic Acids A first stock solution was prepared consisting of [3-(4-iodo-phenoxymethyl)-phenyl]-acetic acid ethyl ester (of intermediate 4; 1.89 g, 4.8 mmol), bis(tri-cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 168 mg, 0.25 mmol), and dioxane (approximately 96 mL). This solution was sonicated and degassed by bubbling nitrogen gas through it. A second stock solution was prepared consisting of potassium carbonate (1.99 g, 14.4 mmol) and water (approximately 9.6 mL). 4 mL of the first stock solution and 0.4 mL of the second stock solution were added to each of a number of tubes containing an aryl-boronic acid. The mixtures were each heated in a microwave oven at 170 degrees for 25 min. To each reaction mixture was added 1 M KOH solution (0.8 mL, 0.8 mmol) and the solutions were heated at 60 degrees overnight. 1 M HCl (0.8 mL, 0.8 mmol) was added to each solution and the reactions were then filtered through silica (1 g) and washed with dimethylacetamide. The solutions were evaporated to dryness using a Genevac system and further dried in the vacuum oven at 50 degrees.; Example 42 [3-(2'-Methoxymethyl-biphenyl-4-yloxymethyl)-phenyl]-acetic acid [3-(2'-Methoxymethyl-biphenyl-4-yloxymethyl)-phenyl]-acetic acid was prepared using general procedure 4 from [3-(4-iodo-phenoxymethyl)-phenyl]-acetic acid ethyl ester (of intermediate 4) and <strong>[126617-98-9]2-methoxymethylphenylboronic acid</strong> (available from Apollo Scientific Ltd., Stockport, UK). Mass spectrum MH+=363.

References: [1]Patent: US2006/122256,2006,A1 .Location in patent: Page/Page column 24; 42.

9
[ 890051-47-5 ]
[ 126617-98-9 ]
6-(2'-methoxymethyl-biphenyl-4-yloxymethyl)-pyridine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A first stock solution was prepared consisting of 6-(4-iodo-phenoxymethyl)-pyridine-2-carboxylic acid methyl ester (of intermediate 5; 1.77 g, 4.8 mmol), bis(tri-cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 168 mg, 0.25 mmol), and dioxane (approximately 100 mL). A second stock solution was prepared consisting of potassium carbonate (1.99 g, 14.4 mmol) and water (approximately 10 mL). The solutions were sonicated and degassed by bubbling nitrogen gas through them. 4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction tube containing 2-methoxymethyl-phenylboronic acid (available from Apollo Scientific Ltd., Stockport, UK; 100 mg, 0.6 mmol). The mixture was heated in a microwave oven at 170 degrees for 25 min, and then 1 M KOH solution (1 equivalent) was added and the reaction mixture was heated in the microwave for 10 minutes at 120 degrees, for 10 minutes at 130 degrees, and at 170 degrees for one hour. The reaction mixture was then filtered through a silica column (1 g) and washed with dimethylacetamide (2×1 mL). The solvent was evaporated to give 6-(2'-methoxymethyl-biphenyl-4-yloxymethyl)-pyridine-2-carboxylic acid. Mass spectrum MH+=350.

References: [1]Patent: US2006/122256,2006,A1 .Location in patent: Page/Page column 40.

10
[ 1217484-57-5 ]
[ 126617-98-9 ]
[ 1217483-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; caesium carbonate;POPd; In water; N,N-dimethyl-formamide; at 150℃; for 0.333333h;Microwave irradiation;	In a 5mL microwave vial, (R)-3-bromo-5-(5-methylpyridin-2-yl)-N-(l -(2- methylpyrimidin-5-yl)ethyl)benzamide (50.00 mg, 0.1216 mrnol), <strong>[126617-98-9]2-(methoxymethyl)phenylboronic acid</strong> (40.36 mg, 0.2431 mmol), cesium carbonate (198.0 mg, 0.6078 mmol), tetra-n-butylammonium iodide (44.90 mg, 0.1216 mmol), and POPd (6.100 mg, 0.01216 mmol) were dissolved in Water (0.09 mL, 5 mmol) and NN-dimethylformamide (0.4 mL, 6 mmol). The reaction mixture was microwaved for 20mins at 150 degrees. The reaction was purified directly by reversed phase HPLC (acetonitrile: water gradient) at pH10. The combined pure fractions were reduced invacuo to afford the title compound as white solid. IH NuMR (DMSO-d6): 9.06 (d, J=7.66 Hz, IH), 8.73 (s, 2H), 8.56-8.54 (m, 2H), 8.22 (t, J=I .49 Hz, IH), 8.01(d, J=8.06 Hz, IH)1 7.93 (t, J=I .49 Hz, IH), 7.74 (dd, J=8.36 &2.39 Hz, IH), 7.55-7.52 (m, IH), 7.45- 7.40 (m, 3H), 5.22 (qt, J=8.24 Hz, IH), 4.29 (s, 2H), 3.22 (s, 3H), 2.59 (s, 3H), 2.35 (s, 3H), 1.55 (d, J=7.29 Hz, 3H).

References: [1]Patent: WO2010/33168,2010,A2 .Location in patent: Page/Page column 87-88.

11
[ 1333107-70-2 ]
[ 126617-98-9 ]
[ 1333107-82-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4823 - 4827.

12
[ 1318261-52-7 ]
[ 126617-98-9 ]
[ 1318261-68-5 ]

References: [1]Organic Letters,2011,vol. 13,p. 4236 - 4239.

13
[ 126617-98-9 ]
[ 345891-28-3 ]
[ 1334598-59-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

14
[ 52711-30-5 ]
[ 126617-98-9 ]

References: [1]Journal of Molecular Structure,2013,vol. 1035,p. 190 - 197.

15
C₁₂H₁₉BO₃ [ No CAS ]
[ 126617-98-9 ]

Yield	Reaction Conditions	Operation in experiment
3.85 g	With hydrogenchloride; In diethyl ether; hexane; water;Inert atmosphere;	The reaction was carried out under argon protection. Diethyl ether (200 mL) was placed in a three-necked round-bottomed flask, equipped with a CO2/acetone bath and magnetic stirrer was cooled down to -70 C. n-Butyllithium (2.5 M in hexanes, 29.9 mL, 74.8 mmol) was slowly added to the stirred solvent. 1-Bromo-2-(methoxymethyl)benzene (2a) (14.32 g, 71.2 mmol) was dropped-in for 10 min while keeping the temperature below -65 C. After 1 h of stirring at that temperature, triethyl borate (12.71 mL, 74.8 mmol) was dropped-in while keeping the temperature below -65 C. The stirring was continued for an additional hour at this temperature. After that time the CO2/acetone bath was removed and aq. HCl (3 M, 50 mL) was quickly added while intense stirring. The temperature rose until about 10 C. The resulting phases were separated and the aqueous phase was extracted twice with diethyl ether (30 mL). The organic phases were combined and about 3/4 of the volume of the solvent removed under reduced pressure. Water (100 mL) was added to the remaining liquid and evaporation was continued for an additional half an hour. The aqueous phase was removed by decantation. The slurry was kept at 4 C for 10 days. After that time a white solid was filtered off. and dried on air to give the crystalline product (3.85 g, 32.5% yield). Anal.: Calcd for C8H11BO3: C 57.89%, H 6.68%; Found: C 57.04%, H 6.56%. 11B NMR (128.3 MHz, CDCl3): delta: 29.6 ppm. 1H NMR (400 MHz, acetone-d6): delta: 3.34 (s, 3H), 4.58 (s, 2H), 7.28-7.38 (m, 3H), 7.46 (s, 2BOH), 7.79-7.81 ppm (m, 1H). 13C NMR (100 MHz, CDCl3): delta 57.0, 76.3, 128.1, 130.0, 130.2, 136.3, 140.3, 183.8 ppm.

References: [1]Journal of Molecular Structure,2013,vol. 1035,p. 190 - 197.

16
[ 18982-54-2 ]
[ 126617-98-9 ]

References: [1]Journal of Molecular Structure,2013,vol. 1035,p. 190 - 197.

17
potassium hydrogen difluoride [ No CAS ]
[ 126617-98-9 ]
potassium 2-(methoxymethyl)phenyl trifluoroborate [ No CAS ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 14012 - 14015.

18
[ 120-80-9 ]
[ 126617-98-9 ]
2-[2-(methoxymethyl)phenyl]-1,3,2-benzodioxaborole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In chloroform; for 3h;Dean-Stark; Reflux;	2-Methoxymethylphenylboronic acid (0.97g, 5.8mmol) and catechol (0.63g, 5.8mmol) were dissolved in 150ml of chloroform and placed in a vessel fitted with a reversed Dean-Stark apparatus for azeotropic water removal. The solution was refluxed for 3h. The crude product was recrystallized from ethyl acetate to give a white solid. Yield: 55%. Elemental anal.: Found: C, 69.27; H, 5.56. Calc. for C14H13BO3: C, 70.04; H, 5.46%. 1H NMR (CDCl3, 400MHz): delta 3.45 (s, 3H), 4.87 (s, 2H), 7.11-7.14 (m, 2H), 7.29-7.31 (m, 2H), 7.37-7.40 (m, 1H) 7.48-7.55 (m, 2H), 8.05 (d, J=7.3Hz, 1H) ppm, 11B NMR (CDCl3, 64MHz): 31.5ppm.

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 116,p. 616 - 621.

19
[ 126617-98-9 ]
[ 148547-19-7 ]
C₁₇H₁₈O₃ [ No CAS ]