1-Nitro-2-carboxyanthraquinone

Base Information

• Chemical Name: 1-Nitro-2-carboxyanthraquinone
• CAS No.: 128-67-6
• Molecular Formula: C15H7 N O6
• Molecular Weight: 297.224
• Hs Code.: 2918300090
• European Community (EC) Number: 204-904-8
• NSC Number: 82322
• DSSTox Substance ID: DTXSID20155768
• Nikkaji Number: J6.571D
• Wikidata: Q83023747
• Mol file: 128-67-6.mol

Synonyms:1-NA-2-CA;1-nitroanthraquinone-2-carboxylic acid

Chemical Property of 1-Nitro-2-carboxyanthraquinone

Chemical Property:

• Vapor Pressure: 5.22E-15mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Boiling Point: 595.1°Cat760mmHg
• Flash Point: 252.3°C
• PSA: 117.26000
• Density: 1.62g/cm³
• LogP: 2.59160
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 297.02733694
• Heavy Atom Count: 22
• Complexity: 539

Purity/Quality:

98%min ^*data from raw suppliers

1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)C(=O)O)[N+](=O)[O-]

Technology Process of 1-Nitro-2-carboxyanthraquinone

There total 8 articles about 1-Nitro-2-carboxyanthraquinone 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: 70.0%

1-nitro-2-methylanthraquinone (129-15-7) → 1-nitroanthraquinone-2-carboxylic acid (128-67-6)

Guidance literature:

With nitric acid;

Reference yield: 60.0%

ethyl 1-nitroanthraquinone-2-carboxylate (80685-73-0) + ethyl 2-cyanoacetate (105-56-6) → 1-nitroanthraquinone-2-carboxylic acid (128-67-6) + 1-cyanoethoxycarbonylmethyl-2-ethoxycarbonylanthraquinone

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 80 ℃; for 1.5h;

Reference yield:

2-methylanthracene-9,10-dione (84-54-8) → 1-nitroanthraquinone-2-carboxylic acid (128-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; potassium nitrate / 5 - 20 °C

2: sulfuric acid; sodium dichromate / water / 11 h / 90 °C / Cooling with ice

With sodium dichromate; sulfuric acid; potassium nitrate; In water;

DOI:10.3390/molecules25071672

upstream raw materials:

1-nitro-2-methylanthraquinone

ethyl 1-nitroanthraquinone-2-carboxylate

ethyl 2-cyanoacetate

sulfuric acid

Downstream raw materials:

Vat Red KKh

1-(N-acetyl-p-toluidino)-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid

2,7-dioxo-3-p-tolyl-2,7-dihydro-3H-naphtho[1,2,3-de]quinoline-4-carboxylic acid

1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid

Refernces

• 1、 Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng. "Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances". . . Retrieved 2020/09/04.
• 2、 Gorelik, M. V.,Lomzakova, V. I.. "REACTION OF α-HALOGENO- AND α-NITROANTHRAQUINONES WITH THE ANIONS OF CH ACIDS IV. REACTION OF 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID WITH CYANOACETIC ESTER AND MALONONITRILE". . p. 2053 - 2055. Retrieved 2007/10/02.