5-Isothiocyanatoalrestatin

Base Information

• Chemical Name: 5-Isothiocyanatoalrestatin
• CAS No.: 103904-10-5
• Molecular Formula: C₁₅H₈N₂O₄S
• Molecular Weight: 312.306
• DSSTox Substance ID: DTXSID40146138
• Nikkaji Number: J1.182.641E
• ChEMBL ID: CHEMBL276870
• Mol file: 103904-10-5.mol

Synonyms:5-isothiocyanatoalrestatin

Chemical Property of 5-Isothiocyanatoalrestatin

Chemical Property:

• Vapor Pressure: 2.39E-16mmHg at 25°C
• Boiling Point: 622.3°Cat760mmHg
• Flash Point: 330.2°C
• PSA: 120.82000
• Density: 1.54g/cm³
• LogP: 1.77160
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 312.02047791
• Heavy Atom Count: 22
• Complexity: 572

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=CC(=CC3=C2C(=C1)C(=O)N(C3=O)CC(=O)O)N=C=S

Technology Process of 5-Isothiocyanatoalrestatin

There total 5 articles about 5-Isothiocyanatoalrestatin 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:

1,8-Naphthalic anhydride (81-84-5) → (5-Isothiocyanato-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid (103904-10-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / conc. H₂SO₄, conc. HNO₃ / 1.5 h / Ambient temperature

2: 79 percent / Et₃N / toluene / 6 h / Heating

3: 74 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h / 2068.6 Torr

4: 10percent aq. NaOH / methanol / 18 h / Ambient temperature

5: acetone; H₂O / 2 h / 0 - 20 °C

With sodium hydroxide; sulfuric acid; hydrogen; nitric acid; triethylamine; palladium on activated charcoal; In methanol; water; ethyl acetate; acetone; toluene;

DOI:10.1021/jm00161a040

Reference yield:

3-nitro-1,8-naphthalic anhydride (3027-38-1) → (5-Isothiocyanato-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid (103904-10-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / Et₃N / toluene / 6 h / Heating

2: 74 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h / 2068.6 Torr

3: 10percent aq. NaOH / methanol / 18 h / Ambient temperature

4: acetone; H₂O / 2 h / 0 - 20 °C

With sodium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In methanol; water; ethyl acetate; acetone; toluene;

DOI:10.1021/jm00161a040

Reference yield:

5-nitro-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester (103884-82-8) → (5-Isothiocyanato-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid (103904-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h / 2068.6 Torr

2: 10percent aq. NaOH / methanol / 18 h / Ambient temperature

3: acetone; H₂O / 2 h / 0 - 20 °C

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; water; ethyl acetate; acetone;

DOI:10.1021/jm00161a040

upstream raw materials:

thiophosgene

5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid

1,8-Naphthalic anhydride

3-nitro-1,8-naphthalic anhydride

Refernces