[ CAS No. 4442-53-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 4442-53-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4442-53-9 ]

SDS Specification

Alternatived Products of [ 4442-53-9 ]

Product Details of [ 4442-53-9 ]

CAS No. :	4442-53-9	MDL No. :	MFCD00239415
Formula :	C₉H₈O₄	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	VCLSWKVAHAJSFL-UHFFFAOYSA-N
M.W :	180.16	Pubchem ID :	78184
Synonyms :

Calculated chemistry of [ 4442-53-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.27
TPSA :	55.76 ?2

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) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	1.16
Log Po/w (MLOGP) :	0.66
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	1.96 mg/ml ; 0.0109 mol/l
Class :	Very soluble
Log S (Ali) :	-1.93
Solubility :	2.14 mg/ml ; 0.0119 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.8
Solubility :	2.84 mg/ml ; 0.0158 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 4442-53-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4442-53-9 ]

* 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 [ 4442-53-9 ]

[ 4442-53-9 ] Synthesis Path-Downstream 1~10

1
[ 4442-53-9 ]
[ 38871-41-9 ]

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 14: 2,3-ETHYLENEDIOXYBENZOYL CHLORIDE By carrying out the procedure as in Preparation 2--Stage B, but replacing 4,5-methylenedioxy-2-nitrobenzoic acid by 2,3-ethylenedioxybenzoic acid, the title product is obtained.
	With thionyl chloride; at 70 - 80℃; for 4h;	General procedure: The starting two acids (<strong>[4442-53-9]2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid</strong> and 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylic acid) shoud be activated by firstly SOCl2: acid (100 mg) and (6-10 mL) was mixed and stirred at reflux 80 ? for 4 hours. The reaction mixture was cooled and evaporated to give reactive acyl chloride obtained as an oil, which would be dissolved in ethyl acetate (5-6 mL) in the next step.
	With thionyl chloride; In N,N-dimethyl-formamide; for 4h;	General procedure: Method B: SOCl2 (10mL) was added to a stirred solution of compound 3 (20mmol) in anhydrous DMF (50mL). The reaction solution was allowed to stir at room temperature for approximately 4h. Then, active compound 4 (15mmol) and metronidazole (15mmol) were dissolved in CH2Cl2 followed by drop wise addition triethylamine and compound 5 was obtained with yield of 85percent. Compound 5 (10mmol), different substituted benzaldehydes (12mmol) and NaOH (15mmol) were dissolved in DMSO (30mL) at room temperature. The appropriate amount of water was then added in the residue and filtered. The resulting solid was collected and washed with cold water, dried and crystallized from anhydrous ethanol to get the desired compounds. All of the synthetic compounds gave satisfactory analytical and spectroscopic data, which were in full accordance with their depicted structures.

With thionyl chloride; at 85℃; for 1h;

Intermediate 35: 2-diazo-1-(2,3-dihvdro-1 ,4-benzodioxin-5-yl)ethanone; A solution of 1 g of 2,3-dihydro-1 ,4-benzodioxin-5-carboxylic acid (5.55 mmole, Aldrich) in 30.7 mL of SOCI2 was stirred at 850C for 1 h in a dry flask under nitrogen atmosphere. The excess of SOCI2 was removed under reduced pressure, the resulting crude oil was <n="76"/>dissolved in 20.3 ml. of MeCN and to this solution, a solution of TMSCHN2 2M in hexane (11.1 mmole, Aldrich) was added dropwise at O0C. The reaction mixture was warmed to RT and stirred for 2 h. A 1 M solution of citric acid was added and then extracted with AcOEt. The organic layer was washed with a saturated solution of NaHCC>3, dried over Na2SO4 and concentrated under reduced pressure. The crude oil was purified by flash chromatography (from CH to CH/AcOEt 80/20) to give the title compound as a yellow oil (489 mg, 42percent). 1H-NMR (500 MHz, CDCI3): delta 4.29-4.34 (2H, m), 4.35-4.40 (2H, m), 6.25 (1 H, s), 6.92 (1 H, t), 7.02 (1 H, dd), 7.46 (1 H, s); m/z (ES): 205 [M+H]+.

Reference： [1]Journal of Organic Chemistry,1948,vol. 13,p. 489,493
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1609 - 1616
[3]Patent: US5332735,1994,A
[4]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 635 - 644
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5870 - 5875
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 220 - 240
[7]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2947 - 2954
[8]Chemistry - A European Journal,2016,vol. 22,p. 12286 - 12289
[9]Journal of Medicinal Chemistry,2017,vol. 60,p. 180 - 201
[10]Journal of Medicinal Chemistry,2018,vol. 61,p. 918 - 933
[11]Patent: WO2008/148853,2008,A1 .Location in patent: Page/Page column 73-74
[12]Organic Letters,2019,vol. 21,p. 2645 - 2649

2
[ 303-38-8 ]
[ 106-93-4 ]
[ 4442-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	Step A 5-Carboxy-2,3-dihydro-1,4-benzodioxin A mixture of 10.8 g (70 mmol) of 2,3-dihydroxybenzoic acid, 38.6 g (280 mmol) of dry potassium carbonate and 24 ml (278 mmol) of 1,2-dibromoethane in 40 ml of N,N-dimethylformamide is heated at 65° C. for 24 hours under an inert atmosphere. After cooling, the reaction mixture is diluted with water and then extracted with ether. The aqueous phase is then acidified with a 3N hydrochloric acid solution and subsequently extracted with dichloromethane. After removal of the solvent by evaporation in vacuo, the residue obtained is recrystallized from toluene to yield the title acid in the form of a white solid. Melting point 193-194° C.

Reference： [1]Journal of Organic Chemistry,1948,vol. 13,p. 489,493
[2]Patent: US5919814,1999,A

3
[ 4442-53-9 ]
[ 148703-15-5 ]
2,3-Dihydro-benzo[1,4]dioxine-5-carboxylic acid 1-butyl-piperidin-4-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 4121 - 4123

5
[ 953772-17-3 ]
[ 4442-53-9 ]
4-{2-[(2,3-Dihydro-benzo[1,4]dioxine-5-carbonyl)-amino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 40℃;	Example 8 Synthesis of 4-{2-[(2,3-Dihydro-benzo[1,4]dioxine-5-carbonyl)-amino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide (Table 2, Compound 110) 4-(2-Amino-benzooxazol-6-yloxy)-pyridine-2-carboxylic acid methylamide (1 eq) and <strong>[4442-53-9]2,3-dihydro-1,4-benzodioxane-5-carboxylic acid</strong> (1 eq) were dissolved in DMF. To this solution were added DIPEA (3 eq) and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (1 eq). The mixture was stirred at 40° C. overnight, then diluted with ethyl acetate and washed once each with 1N HCl, saturated aqueous sodium bicarbonate, and brine, and finally dried with anhydrous sodium sulfate, filtered, and concentrated. This was purified by preparatory reverse phase HPLC. MH+=447.0.

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 42

6
[ 4442-53-9 ]
[ 364765-74-2 ]