3-(Methoxymethylene)-2(3H)-benzofuranone supplier

Name
3-(Methoxymethylene)-2(3H)-benzofuranone
EINECS
CAS No. 40800-90-6
Article Data15
CAS DataBase
Density 1.358 g/cm³
Solubility
Melting Point
Formula C₁₀H₈O₃
Boiling Point 331.1 °C at 760 mmHg
Molecular Weight 176.172
Flash Point 136.6 °C
Transport Information
Appearance powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-(Methoxymethylene)-2(3H)-benzofuranone;3-(a-Methoxy)methylenebenzofuran-2(3H)-one;(3Z)-3-(Methoxymethylene)-1-benzofuran-2(3H)-one;
PSA 35.53000
LogP 1.59290

Synthetic route

: 553-86-6
benzofuran-2(3H)-one

: 149-73-5
trimethyl orthoformate

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With acetic anhydride at 95 - 100℃; Concentration;	96.5%
With acetic anhydride at 40 - 90℃; Temperature;	96.8%
at 110℃; for 21h; Large scale;
With zinc(II) chloride at 110℃; for 4h;

: 67-56-1
methanol

: 3-hydroxymethylenebenzofuran-2(3H)-one potassium salt

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Stage #1: 3-hydroxymethylenebenzofuran-2(3H)-one potassium salt at 10℃; pH=2 - 3; Stage #2: methanol With hydrogenchloride for 4h; Reflux;	95.2%

: 614-75-5
2-Hydroxyphenylacetic acid

: 149-73-5
trimethyl orthoformate

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Stage #1: 2-Hydroxyphenylacetic acid With acetic anhydride at 100℃; for 2h; Inert atmosphere; Large scale; Stage #2: trimethyl orthoformate at 100℃; for 19h; Time; Large scale;	90%
In 2-Methylpropionic anhydride at 100℃; for 10h;	59%
With 2-Methylpropionic anhydride at 100℃; for 10h;	59%
With acetic anhydride at 80 - 100℃; for 6h;

: 40800-88-2
3-formylbenzofuran-2(3H)-one

: 77-78-1
dimethyl sulfate

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Time;	90%

: 614-75-5
2-Hydroxyphenylacetic acid

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With acetic anhydride; trimethyl orthoformate In water; acetic acid; toluene
Multi-step reaction with 2 steps 1: acetic anhydride / 2.5 h / 110 °C / Inert atmosphere; Large scale 2: 21 h / 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: acetic acid; phosphorus pentoxide / toluene / 6 h / Reflux 2: zinc(II) chloride / 4 h / 110 °C View Scheme

: 97-72-3
2-Methylpropionic anhydride

: 614-75-5
2-Hydroxyphenylacetic acid

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With trimethyl orthoformate

: 553-86-6
benzofuran-2(3H)-one

: 614-75-5
2-Hydroxyphenylacetic acid

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With acetic anhydride; trimethyl orthoformate

: 553-86-6
benzofuran-2(3H)-one

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With acetic anhydride; trimethyl orthoformate In methanol; dichloromethane
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / -10 - 0 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: isopropyl alcohol / 20 °C 2.1: sodium hydroxide / methanol / 5 h / 40 °C 2.2: 3 h / Reflux View Scheme

: 70450-82-7
3-(α-hydroxy)methylenebenzofuran-2(3H)-one

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
With sulfuric acid In methanol

: 67-56-1
methanol

: 3-diethylaminemethylidene-2-benzofuranone

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Stage #1: 3-diethylaminemethylidene-2-benzofuranone With sodium hydroxide In methanol at 40℃; for 5h; Stage #2: methanol With sulfuric acid for 3h; Reflux;

: 3-diethylaminemethylidene-2-benzofuranone

: 77-78-1
dimethyl sulfate

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Stage #1: 3-diethylaminemethylidene-2-benzofuranone With sodium hydroxide In methanol; water at 40℃; for 5h; Stage #2: dimethyl sulfate With tetrabutylammomium bromide In methanol; water at 30℃; for 5h;

: 67-56-1
methanol

: 3-dimethylaminomethylene-2-(3H)benzofuranone

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Stage #1: 3-dimethylaminomethylene-2-(3H)benzofuranone With sodium hydroxide In methanol at 40℃; for 5h; Stage #2: methanol With sulfuric acid for 3h; Reflux;

: 77-78-1
dimethyl sulfate

: 3-dimethylaminomethylene-2-(3H)benzofuranone

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Stage #1: 3-dimethylaminomethylene-2-(3H)benzofuranone With sodium hydroxide In methanol; water at 40℃; for 5h; Stage #2: dimethyl sulfate With tetrabutylammomium bromide In methanol; water at 30℃; for 5h;

: 2444-36-2
2'-chloro-benzeneacetic acid

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; copper(II) oxide / water / pH 7 / Autoclave 2: water / 12 h / 100 °C / Autoclave View Scheme

: 553-86-6
benzofuran-2(3H)-one

: 108-24-7
acetic anhydride

: 149-73-5
trimethyl orthoformate

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

Conditions

Conditions	Yield
In water at 100℃; for 12h; Autoclave;

...Expand

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 26537-68-8
benzofurane-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 0 - 60℃; Solvent; Reagent/catalyst; Temperature;	97.5%

: 1193-21-1
4,6-dichloropyrimidine

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 124-41-4
sodium methylate

: 383428-73-7
3-((α)‐2‐(2‐(6‐chloropyrimidin-4‐yl)oxy)phenyl)methyl-3-methoxyacrylate

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 3 - 24℃; for 72h; Temperature; Inert atmosphere; Large scale;	93%

...Expand

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 124-41-4
sodium methylate

: 175971-61-6
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester

Conditions

Conditions	Yield
In methanol at -10℃; for 1h; Inert atmosphere;	86%
In methanol at -5 - 0℃; for 1h;	86%

: 67-56-1
methanol

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 175971-61-6
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester

Conditions

Conditions	Yield
Stage #1: methanol With sodium at -10℃; for 0.5h; Stage #2: 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone for 1h; Inert atmosphere;	86%
With sodium at 0℃; for 1h;

: 67-56-1
methanol

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 124-41-4
sodium methylate

: 175971-61-6
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester

Conditions

Conditions	Yield
at -5 - 0℃; for 1h;	86%

...Expand

: 1193-21-1
4,6-dichloropyrimidine

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 124-41-4
sodium methylate

: 143230-42-6
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone; sodium methylate With 2-methyl-1,4-divinylpiperazine In methanol; acetonitrile at 15 - 20℃; for 0.5h; Stage #2: 4,6-dichloropyrimidine In methanol; acetonitrile for 1h; Solvent; Temperature;	85%
With 2-methyl-1,4-divinylpiperazine In tetrahydrofuran; methanol at 15 - 20℃; for 5h; Solvent; Temperature; Reagent/catalyst;	80%
Stage #1: 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone; sodium methylate With potassium carbonate In methanol; toluene at 0℃; for 0.416667h; Inert atmosphere; Stage #2: 4,6-dichloropyrimidine With 1,4-diaza-bicyclo[2.2.2]octane In methanol; toluene for 1h; Reagent/catalyst; Temperature; Solvent;	55.2%

...Expand

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 70450-82-7
3-(α-hydroxy)methylenebenzofuran-2(3H)-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water
With hydrogenchloride; sodium hydroxide; sulfuric acid In methanol; water

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: sodium salt of 3-(α-hydroxy)methylenebenzofuran-2(3H)-one

Conditions

Conditions	Yield
With sodium hydroxide In water
With hydrogenchloride; sodium hydroxide; sulfuric acid In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 3-hydroxymethylenebenzofuran-2(3H)-one potassium salt

Conditions

Conditions	Yield
With potassium hydroxide In water

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: calcium salt of 3-(α-hydroxy)methylenebenzofuran-2(3H)-one

Conditions

Conditions	Yield
In water

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-24-3
methyl 2-(2-(6-chloro-2-methylpyrimidin-4-yloxy)-phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-25-4
methyl 2-(2-(2,6-dichloropyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-26-5
methyl 2-(2-(6-chloro-2-(methylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-27-6
methyl 2-(2-(6-chloro-2-(o-tolylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-28-7
methyl 2-(2-(6-chloro-2-(m-tolylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-29-8
methyl 2-(2-(6-chloro-2-(p-tolylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-30-1
methyl 2-(2-(6-chloro-2-(pyridin-2-ylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-31-2
(E)-methyl 2-(2-(6-chloro-2-methylpyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 114077-64-4
(E)-methyl 2-(2-(2,6-dichloropyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-32-3
(E)-methyl 2-(2-(6-chloro-2-(methylthio)pyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme

: 40800-90-6
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

: 1394124-33-4
(E)-methyl 2-(2-(6-chloro-2-(o-tolylthio)pyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme

3-(Methoxymethylene)-2(3H)-benzofuranone Specification

The systematic name of 3-(Methoxymethylene)-2(3H)-benzofuranone is (3Z)-3-(methoxymethylidene)-1-benzofuran-2(3H)-one. With the CAS registry number 40800-90-6, it is also named as 2(3H)-Benzofuranone,3-(methoxymethylene)-. In addition, its molecular formula is C₁₀H₈O₃ and molecular weight is 176.17.

The other characteristics of 3-(Methoxymethylene)-2(3H)-benzofuranone can be summarized as: (1)ACD/LogP: 1.80; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 1; (6)Polar Surface Area: 35.53 Å²; (7)Index of Refraction: 1.665; (8)Molar Refractivity: 48.17 cm³; (9)Molar Volume: 129.6 cm³; (10)Polarizability: 19.09×10^-24cm³; (11)Surface Tension: 61 dyne/cm; (12)Density: 1.358 g/cm³; (13)Flash Point: 136.6 °C; (14)Enthalpy of Vaporization: 57.37 kJ/mol; (15)Boiling Point: 331.1 °C at 760 mmHg; (16)Vapour Pressure: 0.000159 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C2Oc1ccccc1/C2=C/OC
(2)InChI: InChI=1/C10H8O3/c1-12-6-8-7-4-2-3-5-9(7)13-10(8)11/h2-6H,1H3/b8-6-
(3)InChIKey: YDHPXCHZYXPZIS-VURMDHGXBS
(4)Std. InChI: InChI=1S/C10H8O3/c1-12-6-8-7-4-2-3-5-9(7)13-10(8)11/h2-6H,1H3/b8-6-
(5)Std. InChIKey: YDHPXCHZYXPZIS-VURMDHGXSA-N

Product Name

3-(Methoxymethylene)-2(3H)-benzofuranone

Synthetic route

3-(Methoxymethylene)-2(3H)-benzofuranone Specification

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