Methyl 5-allyl-3-methoxysalicylate

Base Information

• Chemical Name: Methyl 5-allyl-3-methoxysalicylate
• CAS No.: 85614-43-3
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Hs Code.: 29189900
• European Community (EC) Number: 287-929-7
• DSSTox Substance ID: DTXSID00234843
• Nikkaji Number: J333.906H
• Wikidata: Q72486612
• Mol file: 85614-43-3.mol

Synonyms:85614-43-3;Methyl 5-allyl-3-methoxysalicylate;Methyl 5-Allyl-2-hydroxy-3-methoxybenzoate;methyl 2-hydroxy-3-methoxy-5-prop-2-enylbenzoate;EINECS 287-929-7;Benzoic acid, 2-hydroxy-3-methoxy-5-(2-propenyl)-, methyl ester;Methyl 5-Allyl-2-Hydroxy-3-Methoxy Benzoate;5-Allyl-3-methoxysalicylic Acid Methyl Ester;methyl 5-allyl-2-hydroxy-3-methoxy-benzoate;5-Allyl-2-hydroxy-3-methoxybenzoic Acid Methyl Ester;SCHEMBL16429697;DTXSID00234843;2-hydroxy-3-methoxy-5-(2-propenyl)benzoic acid methyl ester;methyl 3-methoxy-5-allylsalicylate;MFCD04038819;AKOS015838927;CS-W014719;AS-65341;Methyl 5-allyl-3-methoxysalicylate, 97%;FT-0642009;M2204;D81986;A841379;W-104076;methyl 2-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzoate

Chemical Property of Methyl 5-allyl-3-methoxysalicylate

Chemical Property:

• Appearance/Colour: WHITE TO LIGHT YELLOW POWDER, CRYSTALS,CRYSTALLINE POWDER AND/OR CHUNKS
• Vapor Pressure: 0.000133mmHg at 25°C
• Melting Point: 54-58 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 324.1 °C at 760 mmHg
• PKA: 10.10±0.23(Predicted)
• Flash Point: 119.8 °C
• PSA: 55.76000
• Density: 1.144 g/cm³
• LogP: 1.91590
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Toluene
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 222.08920892
• Heavy Atom Count: 16
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

Methyl 5-allyl-3-methoxysalicylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)C(=O)OC)CC=C
• Uses: Methyl 5-Allyl-3-methoxysalicylate is a reactant in the synthesis of Fallypride (F101115), enterobactin scaffolds and allylic amines.

Technology Process of Methyl 5-allyl-3-methoxysalicylate

There total 4 articles about Methyl 5-allyl-3-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: 92.0%

3-methoxy-2-(2-propenyloxy)benzoic acid, methyl ester (96619-89-5) → 2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester (85614-43-3)

Guidance literature:

for 0.75h;

DOI:10.1021/jm00109a013

Reference yield:

3-methoxymethylsalicylate (6342-70-7) → 2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester (85614-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / K₂CO₃ / acetone / 12 h / Heating

2: 92 percent / 0.75 h

With potassium carbonate; In acetone;

DOI:10.1021/jm00109a013

Reference yield:

3-methoxysalicylic acid (877-22-5) → 2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester (85614-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 18 M H₂SO₄ / 58 h / Heating

2: 93 percent / K₂CO₃ / acetone / 12 h / Heating

3: 92 percent / 0.75 h

With sulfuric acid; potassium carbonate; In acetone;

DOI:10.1021/jm00109a013

upstream raw materials:

3-methoxy-2-(2-propenyloxy)benzoic acid, methyl ester

3-methoxysalicylic acid

3-methoxymethylsalicylate

3-methoxy-2-hydroxybenzaldehyde

Downstream raw materials:

3-methoxy-2-[(2-methoxyethoxy)methoxy]-5-(2-propenyl)benzoic acid methyl ester

2,3-dimethoxy-5-propylbenzoic acid

2,3-dimethoxy-5-propylbenzoic acid, methyl ester

(S)-2,3-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-propylbenzamide

Refernces

• 1、 Bishop,Mathis,Gerdes,Whitney,Eaton,Mailman. "Synthesis and in vitro evaluation of 2,3-dimethoxy-5-(fluoroalkyl)-substituted benzamides: High-affinity ligands for CNS dopamine D2 receptors". . p. 1612 - 1624. Retrieved 2007/10/02.