[ CAS No. 57830-14-5 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 57830-14-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 57830-14-5 ]

SDS Specification

Alternatived Products of [ 57830-14-5 ]

Product Details of [ 57830-14-5 ]

CAS No. :	57830-14-5	MDL No. :	MFCD14582822
Formula :	C₁₄H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTQCNYDOVASZJD-UHFFFAOYSA-N
M.W :	226.23	Pubchem ID :	44558580
Synonyms :

Calculated chemistry of [ 57830-14-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.28
TPSA :	35.53 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.45
Log Po/w (XLOGP3) :	2.33
Log Po/w (WLOGP) :	3.0
Log Po/w (MLOGP) :	2.68
Log Po/w (SILICOS-IT) :	3.26
Consensus Log Po/w :	2.74

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.1
Solubility :	0.179 mg/ml ; 0.000793 mol/l
Class :	Soluble
Log S (Ali) :	-2.72
Solubility :	0.436 mg/ml ; 0.00193 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.84
Solubility :	0.00325 mg/ml ; 0.0000144 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Safety of [ 57830-14-5 ]

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 [ 57830-14-5 ]

* 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 [ 57830-14-5 ]

[ 57830-14-5 ] Synthesis Path-Downstream 1~11

1
[ 67-56-1 ]
[ 57830-14-5 ]
[ 1455091-04-9 ]

Yield	Reaction Conditions	Operation in experiment
83%		<strong>[57830-14-5]5-phenoxyisobenzofuran-1(3H)-one</strong> (1.0g, 4.42mmol), xylene 10mL, benzyl triethyl ammonium chloride (300 mg, 1.32 mmol) and boron trifluoride diethyl ether (200 mg, 1.41 mmol) were added to the reaction flask, and the mixture was heated to 100 C dropwise to add thionyl chloride (5.0 g, 42.03 mmol). The reaction was carried out at 135 C for 5 hours. After the reaction was completed by thin layer chromatography, the filtrate was concentrated under reduced pressure. The filtrate was concentrated to 3 mL of methanol. The mixture was stirred at 55 C for 1 hour, then concentrated to dryness under reduced pressure. The potassium carbonate solution and the sodium chloride solution were washed and concentrated to dryness to give the title compound 2c (1.0 g, 83.0%).Used directly in the next step.
87.02 g		To a solid mixture of 5-phenoxy-3H-isobenzofuran-l-one (65.54 g, 0.29 mol), boric acid (538 mg, 8.7 mmol) and triphenylphosphine oxide (2.42 g, 8.7 mmol) was added thionyl chloride (42.3 mL). The resulting mixture was refluxed overnight. After cooled, methanol (300 mL) was slowly added to the reaction mixture. It was then refluxed for 1 h and concentrated. Residue was partitioned between EtOAc and saturated NaHC03 solution. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to provide the title compound (87.02 g, 0.31 mol) as an oil. It was used directly to the next reaction without further purification. lH NMR in CDCI3, delta in ppm: 7.91 (d, 1 H, 8.6 Hz), 7.5-6.9 (m, 7 H), 5.06 (s, 2 H), 3.83 (s, 3 H).
		102351 A reactor was charged with toluene (24 Kg), and stirring was initiated. The reactor was then charged with <strong>[57830-14-5]5-phenoxyphthalide</strong> (56 Kg), thionyl chloride (41 Kg), trimethyl borate (1 Kg), dichlorotriphenylphosphorane (2.5 Kg), and potassium carbonate (77 Kg). The mixture was heated to reflux until reaction completion and solvent was removed leaving 2-chloromethyl-4-phenoxybenzoylchloride. Methanol was charged and the mixture was heated above 50 C until reaction completion. Solvent was removed and replaced with DMF. This solution of the product methyl 2-chloromethyl-4- phenoxybenzoic acid methyl ester in DMF was used directly in the next step (HPLC: 85%).

Reference： [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0199; 0200; 0203; 0204
[2]Patent: WO2013/134660,2013,A1 .Location in patent: Paragraph 0167
[3]Patent: WO2014/14834,2014,A1 .Location in patent: Paragraph 0235

2
[ 64169-34-2 ]
[ 108-95-2 ]
[ 57830-14-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; acetylacetone; copper(I) bromide; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	Add phenol (20.4g, 0.22mol) and DMF 50mL to the reaction flask and start stirring.5-Bromoisobenzofuran-1(3H)-one (34.0 g, 0.16 mmol), acetylacetone (3.2 g, 0.03 mol), cuprous bromide (3.6 g, 0.03 mol), potassium carbonate (at room temperature) 30.8g, 0.22mol), three times of nitrogen replacement, heating to 90 C, stirring reaction overnight, adding 1000 mL of purified water to the reaction solution, suction filtration, the filter cake was dissolved in 800 mL of dichloromethane, and the organic phase was washed with 800 mL of 1N hydrochloric acid solution, with purified water. 1000 mL washing, drying the organic phase, and concentrating to dryness under reduced pressure to give a yellow solid.The title compound 2b (22.5 g, 63%) was obtained.
72.22 g	With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 130℃; for 64h;	A mixture of 5-bromo-3H-isobenzofuran- 1 -one (75.9 g, 0.36 mol) (Sigma-Aldrich), phenol (67.1 g, 0.713 mol), CuCl (17.6 g, 0.178 mol), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 7.33 mL) and cesium carbonate (232.3 g, 0.713 mol) in NMP (200 mL) was heated at 130 C for 64 h. After cooled, reaction mixture was poured into ice/2M HCl mixture (1 L). The mixture was then refluxed for 1 h. After cooled, the solid was collected, rinsed with water and dried in vacuo to provide the title compound (72.22 g, 0.32 mol). lH NMR in DMSO-d6, delta in ppm: 7.82 (dd, 1 H, J = 1.6 Hz, 7.6 Hz), 7.51-7.40 (m, 2 H), 7.3-7.1 (m, 5 H), 5.31 (s, 2 H).
	With potassium carbonate; copper(I) bromide; In N,N-dimethyl-formamide; acetylacetone; at 85℃;	j0234j A reactor was charged with DMF (68 Kg), and stirring was initiated. The reactor was then charged with phenol (51 Kg), acetylacetone (8 Kg), 5-bromophthalide (85 Kg), copper bromide (9 Kg), and potassium carbonate (77 Kg). The mixture was heated above 85 C and maintained until reactioncompletion and then cooled. Water was added. Solid was filtered and washed with water. Solid was dissolved in dichloromethane, and washed with aqueous HC1 and then with water. Solvent was removed under pressure and methanol was added. The mixture was stirred and filtered. Solid was washed with methanol and dried in an oven giving 5-phenoxyphthalide (Yield: 72%, HPLC: 99.6%).

Reference： [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0199-0202
[2]Patent: WO2013/134660,2013,A1 .Location in patent: Paragraph 0166
[3]Patent: WO2014/14834,2014,A1 .Location in patent: Paragraph 0234

3
[ 57830-14-5 ]
[ 1455091-06-1 ]