Cinnabarin

Base Information

• Chemical Name: Cinnabarin
• CAS No.: 146-90-7
• Molecular Formula: C₁₄H₁₀N₂O₅
• Molecular Weight: 286.244
• Hs Code.: 2934999090
• NSC Number: 71698
• UNII: 6FT3OBW0T5
• DSSTox Substance ID: DTXSID30163253
• Nikkaji Number: J5.837H
• Wikidata: Q27264836
• Metabolomics Workbench ID: 137909
• ChEMBL ID: CHEMBL479524
• Mol file: 146-90-7.mol

Synonyms:cinnabarin;cinnabarine

Chemical Property of Cinnabarin

Chemical Property:

• Vapor Pressure: 1.76E-11mmHg at 25°C
• Boiling Point: 516.2°Cat760mmHg
• Flash Point: 266°C
• PSA: 126.65000
• Density: 1.68g/cm³
• LogP: 1.64670
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 286.05897142
• Heavy Atom Count: 21
• Complexity: 605

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1)OC3=CC(=O)C(=C(C3=N2)C(=O)O)N)CO

Technology Process of Cinnabarin

There total 8 articles about Cinnabarin 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:

2-(2-hydroxy-6-hydroxymethyl-anilino)-3,6-dioxo-5-phenoxy-cyclohexa-1,4-dienecarboxylic acid methyl ester (19073-11-1) → Cinnabarin (146-90-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H⁺ / methanol

2: Et₃N / benzene

3: NaN₃ / methanol / 1 h / Ambient temperature

4: H₂ / Raney-Ni

5: LiI, Py / Heating

With pyridine; sodium azide; hydrogen; hydrogen cation; triethylamine; lithium iodide; nickel; In methanol; benzene;

DOI:10.1016/S0040-4039(00)89711-7

Reference yield:

2-ethoxycarbonyloxy-9-hydroxymethyl-3-oxo-3H-phenoxazine-1-carboxylic acid methyl ester (17387-71-2) → Cinnabarin (146-90-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃ / methanol / 1 h / Ambient temperature

2: H₂ / Raney-Ni

3: LiI, Py / Heating

With pyridine; sodium azide; hydrogen; lithium iodide; nickel; In methanol;

DOI:10.1016/S0040-4039(00)89711-7

Reference yield:

2-amino-3-hydroxymethyl-phenol (18274-82-3) → Cinnabarin (146-90-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H⁺ / methanol

2: Et₃N / benzene

3: NaN₃ / methanol / 1 h / Ambient temperature

4: H₂ / Raney-Ni

5: LiI, Py / Heating

With pyridine; sodium azide; hydrogen; hydrogen cation; triethylamine; lithium iodide; nickel; In methanol; benzene;

DOI:10.1016/S0040-4039(00)89711-7

upstream raw materials:

cinnabarine methylester

2-amino-3-hydroxymethyl-phenol

3-hydroxyanthranilic acid

2-(2-hydroxy-6-hydroxymethyl-anilino)-3,6-dioxo-5-phenoxy-cyclohexa-1,4-dienecarboxylic acid methyl ester