Methyl 4-amino-5-thiocyanato-o-anisate

Base Information

• Chemical Name: Methyl 4-amino-5-thiocyanato-o-anisate
• CAS No.: 59168-56-8
• Molecular Formula: C10H10N2O3S
• Molecular Weight: 238.267
• European Community (EC) Number: 261-639-0
• UNII: 7MFH7BCA4X
• DSSTox Substance ID: DTXSID40207894
• Nikkaji Number: J308.637B
• Wikidata: Q72487038
• Mol file: 59168-56-8.mol

Synonyms:59168-56-8;methyl 4-amino-2-methoxy-5-thiocyanatobenzoate;Methyl 4-amino-5-thiocyanato-o-anisate;Methyl 4-amino-2-methoxy-5-thiocyanobenzoate;4-AMINO-2-METHOXY-5-THIOCYANATOBENZOIC ACID METHYL ESTER;7MFH7BCA4X;EINECS 261-639-0;UNII-7MFH7BCA4X;SCHEMBL8068503;DTXSID40207894;Benzoic acid, 4-amino-2-methoxy-5-thiocyanato-, methyl ester;C14E8;BCP34089;AKOS015891038;SB80603;FT-0671463;4-Amino-2-methoxy-5-thiocyanatobenzoicacid methyl ester

Chemical Property of Methyl 4-amino-5-thiocyanato-o-anisate

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 2.5E-07mmHg at 25°C
• Melting Point: 160-165°C
• Refractive Index: 1.603
• Boiling Point: 422 °C at 760 mmHg
• Flash Point: 209 °C
• PSA: 110.64000
• Density: 1.35 g/cm³
• LogP: 2.21838
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 238.04121336
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-Amino-2-methoxy-5-thiocyanobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1C(=O)OC)SC#N)N
• Uses: Methyl 4-Amino-2-methoxy-5-thiocyanobenzoate is an Amisulpride (A633250) impurity.

Technology Process of Methyl 4-amino-5-thiocyanato-o-anisate

There total 3 articles about Methyl 4-amino-5-thiocyanato-o-anisate 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: 95.0%

Methyl 4-amino-2-methoxybenzoate (27492-84-8) + ammonium thiocyanate (1147550-11-5) → methyl 4-amino-2-methoxy-5-thiocyanatobenzoate (59168-56-8)

Guidance literature:

With bromine; In methanol; at 5 - 20 ℃; for 4h;

Reference yield:

Methyl 4-amino-2-methoxybenzoate (27492-84-8) + potassium thioacyanate (333-20-0) → methyl 4-amino-2-methoxy-5-thiocyanatobenzoate (59168-56-8)

Guidance literature:

With bromine; acetic acid; at 20 ℃;

Reference yield:

4-Aminosalicylic acid (65-49-6) → methyl 4-amino-2-methoxy-5-thiocyanatobenzoate (59168-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale

2: bromine / methanol / 5 - 15 °C / Industry scale

With tetrabutylammomium bromide; bromine; potassium hydroxide; In methanol; acetone;

upstream raw materials:

Methyl 4-amino-2-methoxybenzoate

potassium thioacyanate

ammonium thiocyanate

4-Aminosalicylic acid

Downstream raw materials:

methyl 4-amino-5-(ethylthio)-2-methoxybenzoate

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

amisulpride

2-methoxy-4-amino-5-methylthio benzoic acid

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR PREPARATION OF AMISULPRIDE". Page/Page column 11. . Retrieved 2012/01/06.