Methyl 4-methoxysalicylate

Base Information

• Chemical Name: Methyl 4-methoxysalicylate
• CAS No.: 5446-02-6
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29189900
• European Community (EC) Number: 226-657-5
• NSC Number: 17154
• UNII: 2R86H93L9U
• DSSTox Substance ID: DTXSID00202860
• Nikkaji Number: J150.024D
• Wikidata: Q72492699
• Metabolomics Workbench ID: 139731
• ChEMBL ID: CHEMBL502178
• Mol file: 5446-02-6.mol

Synonyms:Methyl 4-methoxysalicylate;Methyl 2-hydroxy-4-methoxybenzoate;5446-02-6;Benzoic acid, 2-hydroxy-4-methoxy-, methyl ester;Methyl-4-methoxysalicylate;2-Hydroxy-4-methoxybenzoic Acid Methyl Ester;2-hydroxy-4-methoxy-benzoic acid methyl ester;4-Methoxysalicylic Acid Methyl Ester;MFCD00008424;NSC-17154;Methyl 4-methoxy salicylate;Methyl 2-Hydroxy-p-anisate;SCHEMBL294143;CHEMBL502178;2-methoxycarbonyl-5-methoxyphenol;DTXSID00202860;Methyl 4-methoxysalicylate, 98%;Methyl2-hydroxy-4-methoxybenzoate;2R86H93L9U;methyl 4-methoxy,2-hydroxybenzoate;methyl 4-methoxy-2-hydroxybenzoate;AMY18269;NSC17154;EINECS 226-657-5;methyl 2-hydroxy-4-methoxy-benzoate;NSC 17154;STK279065;methyl 4-methoxy-2-oxidanyl-benzoate;AKOS000121550;Methyl 2-hydroxy-4-methoxybenzoate #;CS-W009087;PS-6101;AC-23898;p-Anisic acid, 2-hydroxy-, methyl ester;SY008082;FT-0635717;M1797;EN300-15505;A830195;W-105622;Z24769843;(6E)-6-(Hydroxymethoxymethylene)-3-methoxy-2,4-cyclohexadien-1-one;2,4-Cyclohexadien-1-one, 6-(hydroxymethoxymethylene)-3-methoxy-, (6E)-;1572051-39-8

Chemical Property of Methyl 4-methoxysalicylate

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.00134mmHg at 25°C
• Melting Point: 50-53 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 288.6 °C at 760 mmHg
• Flash Point: 113.9 °C
• PSA: 55.76000
• Density: 1.216 g/cm³
• LogP: 1.18740
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in acetone. Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

Methyl 4-Methoxysalicylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)C(=O)OC)O
• Uses: Methyl 4-methoxysalicylate (methyl 2-hydroxy-4-methoxybenzoate) was used in the enantioselective synthesis of (+)-coriandrone A and B, two bioactive natural products.

Technology Process of Methyl 4-methoxysalicylate

There total 18 articles about Methyl 4-methoxysalicylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

methanol (67-56-1) + 4-methoxysalicylic acid (2237-36-7) → 4-methoxymethylsalicylate (5446-02-6)

Guidance literature:

With sulfuric acid; for 48h; Reflux;

DOI:10.1007/s00044-018-2197-6

Reference yield: 96.0%

4-methoxysalicylic acid (2237-36-7) + methyl iodide (74-88-4) → 4-methoxymethylsalicylate (5446-02-6)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 40 ℃; for 16h; Inert atmosphere;

DOI:10.1128/AAC.00670-16

Reference yield: 93.0%

methyl 2, 4-dimethoxybenzoate (2150-41-6) → 4-methoxymethylsalicylate (5446-02-6)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at -5 - 25 ℃;

DOI:10.3184/030823410X12708998015900

upstream raw materials:

diazomethane

4-hydroxysalicylic acid

4-methoxysalicylic acid

dimethyl sulfate

Downstream raw materials:

3-(2-Hydroxy-4-methoxybenzoyl)-1-phenyl-2-pyrrolidinon

2-hydroxy-4 methoxybenzonitrile

4-methoxy-2-(trifluoro-methanesulfonyloxy)-benzoic acid methyl ester

methyl 5-bromo-2-hydroxy-4-methoxybenzoate

Refernces

• 1、 Suresh Babu,China Raju,Srinivas,Madhusudana Rao. "Highly efficient and chemoselective cleavage of prenyl ethers using ZrCl4/NaBH4". . p. 2525 - 2528. Retrieved 2003.
• 2、 Depa, Manmohan Reddy,Potla, Suneetha,Narkhede, Umesh C.,Jadhav, Vinod D.,Sridhar, Gattu,Vidavalur, Siddaiah. "Total synthesis of Neocosmosin A". . p. 2817 - 2823. Retrieved 2021/07/26.
• 3、 -. "BRARTEMICIN ANALOGUES". Page/Page column 47-48; 65. . Retrieved 2019/05/22.