[ CAS No. 7169-35-9 ] {[proInfo.proName]}

Name: 7169-35-9|4-Methoxybenzofuran-3(2H)-one|95%
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Quality Control of [ 7169-35-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7169-35-9 ]

SDS Specification

Alternatived Products of [ 7169-35-9 ]

Product Details of [ 7169-35-9 ]

CAS No. :	7169-35-9	MDL No. :	MFCD12828273
Formula :	C₉H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IVSCFNOAUOCHJV-UHFFFAOYSA-N
M.W :	164.16	Pubchem ID :	639146
Synonyms :

Calculated chemistry of [ 7169-35-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.7
TPSA :	35.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	1.44
Log Po/w (WLOGP) :	1.27
Log Po/w (MLOGP) :	0.43
Log Po/w (SILICOS-IT) :	2.14
Consensus Log Po/w :	1.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.4 mg/ml ; 0.00853 mol/l
Class :	Soluble
Log S (Ali) :	-1.79
Solubility :	2.65 mg/ml ; 0.0162 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.7
Solubility :	0.331 mg/ml ; 0.00201 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 7169-35-9 ]

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 [ 7169-35-9 ]

* 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.

Upstream synthesis route of [ 7169-35-9 ]
Downstream synthetic route of [ 7169-35-9 ]

[ 7169-35-9 ] Synthesis Path-Upstream 1~1

1
[ 105285-09-4 ]
[ 7169-35-9 ]
[ 3147-64-6 ]
[ 105285-13-0 ]
[ 29219-06-5 ]
[ 86788-62-7 ]
[ 123-11-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 32, p. 4822 - 4829

[ 7169-35-9 ] Synthesis Path-Downstream 1~19

1
[ 135746-09-7 ]
[ 7169-35-9 ]
[ 57060-62-5 ]
[ 60188-58-1 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 4979 - 4990
[2]Tetrahedron,1991,vol. 47,p. 4979 - 4990
[3]Tetrahedron,1991,vol. 47,p. 4979 - 4990

2
[ 135746-09-7 ]
[ 7169-35-9 ]
[ 57060-62-5 ]
[ 60188-58-1 ]
[ 135746-16-6 ]
[ 135746-16-6 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 4979 - 4990

3
[ 135746-16-6 ]
[ 7169-35-9 ]
[ 135746-22-4 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 9929 - 9938

4
[ 145694-70-8 ]
[ 7169-35-9 ]
2-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-4-methoxy-benzofuran-3-one [ No CAS ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 9929 - 9938

5
[ 145694-69-5 ]
[ 7169-35-9 ]
4-Methoxy-2-[1-(2-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-benzofuran-3-one [ No CAS ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 9929 - 9938

7
[ 150-19-6 ]
[ 107-14-2 ]
[ 7169-35-9 ]

Yield	Reaction Conditions	Operation in experiment
13%	zinc(II) chloride;	EXAMPLE 9 4-Methoxy-3-benzofuranone (2) and 6-methoxy-3-benzofuranone (3) These compounds were prepared from 3-methoxyphenol (1) (6 ml, 55 mmol), ZnCl2 (8.2 g, 60 mmol), and chloroacetonitrile (4.2 g, 66 mmol) in dry ether (100 ml). Purification of the crude product by column chromatography (eluent: CH2Cl2/MeOH: 99/1) gave (2) (1.147 g, 13%), a single compound by HPLC (98% pure, recrystallized from EtOH). 1H-NMR (Acetone-d6, 400 MHz): (7.45 (1 H, d); 6.64 (2 H, m); 4.62 (s, 2 H); 3.95 (s, 3 H) and the more polar compound (3) (1.48 g, 17%). HPLC (84% purity). 1H-NMR (Acetone -d6): delta (400 MHz): values corresponded to previous synthesis of (3).

Reference： [1]Patent: US6307070,2001,B1

8
[ 7169-35-9 ]
[ 1186320-51-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 6h;Reflux;	A mixture of <strong>[7169-35-9]4-methoxy-benzofuran-3-one</strong> (CAS 7169-35-9) (4.9 g, 19 mmol), sodium acetate (3.06 g, 38 mmol) and hydroxylamine hydrochloride (2.58 g, 38 mmol) in ethanol (40 ml) was refluxed for 6 h. Cooled to room temperature, filtered the precipitate off, washed with ethanol and dried in high vacuum to give <strong>[7169-35-9]4-methoxy-benzofuran-3-one</strong> oxime as a white solid (5.93 g, 100%); MS: m/e=180.2 (M+H+).
100%	With hydroxylamine hydrochloride; sodium acetate; In ethanol;Reflux;	Step A: A mixture of <strong>[7169-35-9]4-methoxy-benzofuran-3-one</strong> (CAS 7169-35-9) (4.9 g, 19 mmol), sodium acetate (3.06 g, 38 mmol) and hydroxylamine hydrochloride (2.58 g, 38 mmol) in EtOH (40 ml) was refluxed for 6 h. Cooled to room temperature, filtered the precipitate off, washed with EtOH and dried in high vacuum to give <strong>[7169-35-9]4-methoxy-benzofuran-3-one</strong> oxime as a white solid (5.93 g, 100%); MS: m/e=180.2 (M+H+).
88%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 4h;Reflux;	Step A: 4-Methoxy-benzofuran-3-one oxime A mixture of <strong>[7169-35-9]4-methoxy-benzofuran-3-one</strong> (CAS 7169-35-9) (30 g, 183 mmol; HPLC 1.241 min), sodium acetate (30.9 g, 375 mmol) and hydroxylamine hydrochloride (5.14 g, 57 mmol) in ethanol (310 ml) was refluxed for 4 h. Cooled to 23 C., filtered the precipitate off, washed with aqueous ethanol and dried in high vacuum to give the title compound as a light red solid (27.74 g, 88%; HPLC 1.448 min); MS (ISP) m/e=180.2 [(M+H)+].

Reference： [1]Patent: US2009/227583,2009,A1 .Location in patent: Page/Page column 23-24
[2]Patent: US2009/227584,2009,A1 .Location in patent: Page/Page column 15
[3]Patent: US2010/63037,2010,A1 .Location in patent: Page/Page column 21-22

9
[ 7169-35-9 ]
C₉H₁₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In ethanol;Reflux;	Step A: 4-Methoxy-benzofuran-3-one oxime A mixture of <strong>[7169-35-9]4-methoxy-benzofuran-3-one</strong> (CAS no: 7169-35-9) (4.9 g, 19 mmol), sodium acetate (3.06 g, 38 mmol) and hydroxylamine hydrochloride (2.58 g, 38 mmol) in ethanol (40 mL) was refluxed for 6 h. Cooled to 23 C., filtered the precipitate off, washed with ethanol and dried in high vacuum to give the title compound as a white solid (5.93 g, 100%); MS: m/e=180.2 (M+H+).

Reference： [1]Patent: US2009/227570,2009,A1 .Location in patent: Page/Page column 35

10
methyl 2-(2-ethoxy-2-oxoethoxy)-6-methoxybenzoate [ No CAS ]
[ 7169-35-9 ]

Reference： [1]Patent: WO2016/86158,2016,A1

11
2-(carboxymethoxy)-6-methoxybenzoic acid [ No CAS ]
[ 7169-35-9 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of dicarboxylic acid 40 (3.30 g, 14.59 mmol) and sodium acetate (2.92 g, 35.57 mmol) in aceticanhydride (29 mL) was refluxed for 4 h. The reaction was then cooled to room temperature, poured into ice water (150 mL), and the resulting mixture was stirred for 20 mm. It was then extracted with CH2C12 (100 mL) and the organic layer was dried over Na2SO4 and concentrated to give a dark-brown oil (3.06 g, difficult to remove residual Ac20) . Tothis material was added 1M aqueous HC1 (30 mL), and the mixture was refluxed for 2 h, cooled to room temperature, and extracted with CH2C12 (3 x 30 mL) . The combined organics were washed with water (30 mL), dried over Na2SO4, and concentrated to provide a dark-red solid (2.31 g) . This material was triturated with boiling Et20 and then cooled to0 c and the solids collected by filtration, washing 3x with ice-cold Et20. The product 41 was thus obtained as a pale, reddish-brown solid containing minor impurities (1.01 g, 42% over 2 steps) . ?H NNR (500 MHZ, cDC13) oe 7.52 (t, J- 8.3 Hz, 1H), 6.68 (d, J= 8.3 Hz, 1H), 6.47 (d, J = 8.2 Hz, 1H), 4.60 (s, 2H), 3.96 (s, 3H); ?3C N (126 MHz, CDC13) oe 197.4, 175.4, 158.4, 139.6, 110.7, 105.6, 103.3, 74.9, 56.3;LR-MS calcd. for CgH903 [M+H) 165.06, found 164.97.

Reference： [1]Patent: WO2016/86158,2016,A1 .Location in patent: Page/Page column 142; 143; 144

12
[ 7169-35-9 ]
2-(4-methoxybenzofuran-3-yl)ethanol [ No CAS ]

Reference： [1]Patent: WO2016/86158,2016,A1

13
[ 7169-35-9 ]
3-(2-bromoethyl)-4-methoxybenzofuran [ No CAS ]

Reference： [1]Patent: WO2016/86158,2016,A1

14
[ 7169-35-9 ]
[ 1099-45-2 ]
ethyl 2-(4-methoxybenzofuran-3-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 41h;Reflux;	A solution of 41 (1equivalent) and (carbethoxymethylene) triphenyiphosphorane (1. 1equivalent) in anhydrous toluene (0.30 M, based on benzofuranone) wasrefluxed until TLC indicated the consumption of starting material andthen concentrated in vacuo. The resulting material was triturated with 9:1 hexanes:EtOAc (-7 mL per mmol substrate) and filtered, and the remaining solids were washed with additional portions of 9:1 hexanes:EtOAc (3 x -3 mL per mmol substrate) . The combined filtrateswere concentrated to give the crude product 42, which was purified by column chromatography (9:1 hexanes:EtQAc) to provide a pale-yellow oil still containing minor impurities (409 mg, <58%) . ?H NMR (500 MHz, CDC13) oe 7.49 (s, 1H), 7.19 (t, J- 8.1 Hz, 1H), 7.08 (d, J= 8.3 Hz, lH), 6.62 (d, J = 8.0 Hz, 1H), 4.20 (q, J = 7.1 Hz, 2H), 3.87 (s,3H), 3.84 (s, 2H), 1.27 (t, J = 7.1 Hz, 3H); ?3C NMR (126 MHz, CDC13)171.5, 156.7, 154.8, 141.6, 125.3, 117.5, 113.3, 104.9, 103.2, 60.9,55.5, 30.9, 14.4; LR-MS calcd. for C13H1s04 [M+H] 235.10, found234.98.

Reference： [1]Patent: WO2016/86158,2016,A1 .Location in patent: Page/Page column 142; 144

15
[ 22833-69-8 ]
[ 7169-35-9 ]

Reference： [1]Patent: WO2016/86158,2016,A1

16
[ 699-83-2 ]
[ 7169-35-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 195 - 208

17
[ 19278-81-0 ]
[ 74-88-4 ]
[ 7169-35-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere;	To a solution of 4-hydroxybenzofuran-3(2H)-one (31, 2.0 mmol)in anhydrous DMF (10 mL) was added successively anhydrous potassium carbonate (3.0 mmol) and iodomethane (2.2 mmol). After stirring for 3 h at 80 C, the reaction mixture was cooled to rt, quenched with water (30 mL), and extracted with dichloromethane (3 x 20 mL). The combined organic phases werewashed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 30/1) to afford the title compound. Bright yellow solid, yield 93%; 1H NMR (400 MHz, CDCl3) delta 7.49-7.40 (m, 1H), 6.61 (d, J = 8.4 Hz, 1H), 6.40 (d, J = 8.4 Hz, 1H),4.52 (s, 2H), 3.89 (s, 3H).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 195 - 208

18
[ 121-32-4 ]
[ 7169-35-9 ]
(Z)-2-(3-ethoxy-4-hydroxybenzylidene)-4-methoxybenzofuran-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With aluminum oxide; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: To a solution of benzofuran-3(2H)-one (1.0 mmol) and benzaldehyde(1.0 mmol) in dichloromethane (6 mL) was addedaluminum oxide (30.0 mmol) at room temperature. After stirringfor 6 h, the reaction mixture was filtered off. The filtrate wasconcentrated under vacuum and the residue was purified by flash chromatography on silica gel to give the desired compound.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 195 - 208

19
[ 105285-09-4 ]
[ 7169-35-9 ]
[ 3147-64-6 ]
[ 105285-13-0 ]
[ 29219-06-5 ]
[ 86788-62-7 ]
2,3-dihydro-3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one [ No CAS ]
[ 123-11-5 ]

Yield	Reaction Conditions	Operation in experiment
		2'-Hydroxy-4,6'-dimethoxychalcone (5.0 mg, 0.0176 mmol) was dissolved in 400 muL MeOH and 200 muL H2O , and sodium carbonate (9.3 mg, 0.0880 mmol) was added at room temperature (25°C-28°C) for 30 min in nuclear magnetic tube. Then H2O2 (4.5 muL, 0.0440 mmol) was added in the mixture. After adding H2O2, samples were analysed by LCMS depending on different time (Figure S1).

Reference： [1]Tetrahedron,2017,vol. 73,p. 4822 - 4829

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Ghs Precautionary Statements

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Code	Phrase
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P321
P322
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 7169-35-9 ] {[proInfo.proName]}

Quality Control of [ 7169-35-9 ]

Related Doc. of [ 7169-35-9 ]

Product Details of [ 7169-35-9 ]

Calculated chemistry of [ 7169-35-9 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

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Medicinal Chemistry

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Application In Synthesis of [ 7169-35-9 ]

[ 7169-35-9 ] Synthesis Path-Upstream 1~1

[ 7169-35-9 ] Synthesis Path-Downstream 1~19

Related Functional Groups of [ 7169-35-9 ]

Ethers

Ketones

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Benzofurans

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[ 7169-35-9 ]

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[ 7169-35-9 ]