5-Methoxybenzofuran-3(2H)-one
- Product Name
- 5-Methoxybenzofuran-3(2H)-one
- CAS No.
- 39581-55-0
- Chemical Name
- 5-Methoxybenzofuran-3(2H)-one
- Synonyms
- AKOS BC-0911;5-METHOXY-BENZOFURAN-3-ONE;5-Nitro-3-Benzofuranone (2);5-methoxy-1-benzofuran-3-one;5-methoxybenzofuran-3(2H)-one;5-Methoxy-3(2H)-benzofuranone;3(2H)-Benzofuranone, 5-Methoxy-;5-Methoxy-1-benzofuran-3(2H)-one;1H-1,4-Diazepine,hexahydro-4-(phenylmethyl)-
- CBNumber
- CB3840863
- Molecular Formula
- C9H8O3
- Formula Weight
- 164.16
- MOL File
- 39581-55-0.mol
5-Methoxybenzofuran-3(2H)-one Property
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- Appearance
- Orange to reddish brown Solid
- InChI
- InChI=1S/C9H8O3/c1-11-6-2-3-9-7(4-6)8(10)5-12-9/h2-4H,5H2,1H3
- InChIKey
- VKHVAQOGXRYNNQ-UHFFFAOYSA-N
- SMILES
- O1C2=CC=C(OC)C=C2C(=O)C1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- M341328
- Product name
- 5-Methoxybenzofuran-3(2H)-one
- Packaging
- 10mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 5188AB
- Product name
- 5-Methoxy-1-benzofuran-3(2H)-one
- Packaging
- 250mg
- Price
- $173
- Updated
- 2021/12/16
- Product number
- 5188AB
- Product name
- 5-Methoxy-1-benzofuran-3(2H)-one
- Packaging
- 1g
- Price
- $365
- Updated
- 2021/12/16
- Product number
- CHM0079552
- Product name
- 5-METHOXY-BENZOFURAN-3-ONE
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $968.97
- Updated
- 2021/12/16
- Product number
- CHM0079552
- Product name
- 5-METHOXY-BENZOFURAN-3-ONE
- Purity
- 95.00%
- Packaging
- 2.5G
- Price
- $1445.42
- Updated
- 2021/12/16
5-Methoxybenzofuran-3(2H)-one Chemical Properties,Usage,Production
Synthesis
5-Methoxybenzofuran-3(2H)-one is synthesised using 2-chloro-1-(2-hydroxy-5-methoxyphenyl)ethanone as raw material by chemical reaction. The specific synthesis steps are as follows:
To an ice-cooled solution of boron trichloride (1.2 equiv., 10 mmol, 10 ml of a solution of 1M BC13 in dichloromethane) under N2-atmosphere was added dropwise a solution of J (1 g, 8 mmol,) in dichloromethane (5 ml). Then, chloroacetonitrile (0.7 g, 10 mmol, 1.2 equiv. ) was added dropwise, followed by aluminum(III) chloride (0.5 g, 4 mmol, 0.5 equiv. ) in one portion. The reaction mixture was allowed to warm up to room temperature and was stirred for 6 h. The reaction mixture was diluted with dichloromethane and quenched with IN hydrochloric acid at 0°C. After stirring for 10 min, the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried (MgS04) and concentrated Purification by flash chromatography on silica gel (eluent: dichloromethane) afforded the desired product K (1 g, yield = 60percent). Intermediate K (0.15 g, 0.75 mmol, I equiv. ) and potassium acetate (0.22 g, 2.2 mmol, 3 equiv. ) were refluxed in ethanol (10 ml) for 1 h. After cooling, the reaction mixture was filtered and concentrated. The residue was mixed with water, and acidified with IN hydrochloric acid to pH = 1. The aqueous solution was extracted with ethyl acetate, the combined extracts were dried (MgS04), filtered and concentrated to afford the desired product L (110 mg, yield = 90 percent) as a pink solid The experimental procedures for the condensation reaction of compound L with 4-nitroaniline in acetic acid to form compound M, followed by Vilsmeier-Haack formulation and subsequent Knoevenagel condensation of the benzofuran carbaldehyde N with ethyl cyanoacetate to form compound 0, and finally, intramolecular cyclisation to compound 37 were performed using analogous procedures as exemplified in example 1 for the synthesis of compound f starting from compound a. Compound 37 was obtained as a yellow powder (30 mg, purity (LC) = 80 percent).
References
[1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 12, p. 5950 - 5957
[2] Patent: WO2005/111035, 2005, A1. Location in patent: Page/Page column 78-79
[3] Patent: CN107365322, 2017, A. Location in patent: Paragraph 0098; 0102
[4] Organic Letters, 2008, vol. 10, # 4, p. 573 - 576
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 3, p. 909 - 918
5-Methoxybenzofuran-3(2H)-one Preparation Products And Raw materials
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View Lastest Price from 5-Methoxybenzofuran-3(2H)-one manufacturers
- Product
- 5-Methoxy-3-Benzofuranone 39581-55-0
- Price
- US $0.00/KG
- Min. Order
- 1g
- Purity
- 98%min
- Supply Ability
- 50kgs/month
- Release date
- 2021-11-14
- Product
- 5-METHOXY-BENZOFURAN-3-ONE 39581-55-0
- Price
- US $0.00/g
- Min. Order
- 1g
- Purity
- 95%min
- Supply Ability
- 20kg/month
- Release date
- 2019-12-25