Tiacrilast

Base Information

• Chemical Name: Tiacrilast
• CAS No.: 78299-53-3
• Molecular Formula: C₁₂H₁₀N₂O₃S
• Molecular Weight: 262.289
• Hs Code.: 2933990090
• UNII: 74L3DXN051
• ChEMBL ID: CHEMBL337379
• DSSTox Substance ID: DTXSID801167245
• NCI Thesaurus Code: C73059
• Nikkaji Number: J22.781A
• Wikidata: Q27266294
• Mol file: 78299-53-3.mol

Synonyms:3-(6-(methylthio)-4-oxo-4H-quinazolin-3-yl)-2-propenoic acid;Ro 223747;Ro-22-3747;tiacrilast

Chemical Property of Tiacrilast

Chemical Property:

• Vapor Pressure: 8.67E-11mmHg at 25°C
• Boiling Point: 499.3°C at 760 mmHg
• Flash Point: 255.8°C
• PSA: 97.49000
• Density: 1.38g/cm³
• LogP: 1.67370
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 262.04121336
• Heavy Atom Count: 18
• Complexity: 408

Purity/Quality:

99% ^*data from raw suppliers

TIACRILAST 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=CC2=C(C=C1)N=CN(C2=O)C=CC(=O)O
• Isomeric SMILES: CSC1=CC2=C(C=C1)N=CN(C2=O)/C=C/C(=O)O

Technology Process of Tiacrilast

There total 5 articles about Tiacrilast 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: 81.0%

trans-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid methyl ester (78299-52-2) → trans-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid (78299-53-3)

Guidance literature:

With hydrogenchloride; In various solvent(s); for 0.5h; Heating;

DOI:10.1021/jm00357a018

Reference yield:

5-methylthio-2-nitrobenzoic acid (68701-32-6) → trans-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid (78299-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 19 h / 2585.7 Torr

2: 92 percent / 4 h / 140 - 145 °C

3: 1.) NaH / 1.) DMF, 50 deg C, 30 min, 2.) DMF, 50 deg C, 1 h

4: 81 percent / 6 N HCl / various solvent(s) / 0.5 h / Heating

With hydrogenchloride; hydrogen; sodium hydride; palladium on activated charcoal; In ethanol;

DOI:10.1021/jm00357a018

Reference yield:

5-chloro-2-nitrobenzoic acid (2516-95-2) → trans-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid (78299-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Na₂S, NaOH, 2.) NaOH / 1.) H₂O, from 52 deg C to 55 deg C, 2.5 h, 2.) H₂O, reflux, 1 h

2: 92 percent / 4 h / 140 - 145 °C

3: 1.) NaH / 1.) DMF, 50 deg C, 30 min, 2.) DMF, 50 deg C, 1 h

4: 81 percent / 6 N HCl / various solvent(s) / 0.5 h / Heating

With hydrogenchloride; sodium sulfide; sodium hydroxide; sodium hydride; In various solvent(s);

DOI:10.1021/jm00357a018

upstream raw materials:

trans-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid methyl ester

5-chloro-2-nitrobenzoic acid

5-methylthio-2-nitrobenzoic acid

2-amino-5-(methylsulfanyl)benzoic acid