2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-8-carboxylic acid

Base Information

• Chemical Name: 2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-8-carboxylic acid
• CAS No.: 167902-99-0
• Molecular Formula: C9H5NO5
• Molecular Weight: 207.142
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10438552
• Wikidata: Q82254320
• Mol file: 167902-99-0.mol

Synonyms:167902-99-0;2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-8-carboxylic acid;2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-8-carboxylic acid;2,4-dioxo-1H-3,1-benzoxazine-8-carboxylic acid;2,4-dioxo-2,4-dihydro-1H-3,1-benzoxazine-8-carboxylic acid;SCHEMBL465947;DTXSID10438552;HVIZTWSCWFPXES-UHFFFAOYSA-N;2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-8-carboxylicacid;MFCD09865033;AKOS005073785;SS-2958;CS-0316436;A920369;J-507251;2,4-Dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-8-carboxylic acid

Chemical Property of 2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-8-carboxylic acid

Chemical Property:

• PSA: 100.37000
• LogP: 0.17950
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 207.01677226
• Heavy Atom Count: 15
• Complexity: 327

Purity/Quality:

97% ^*data from raw suppliers

2,4-Dioxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-8-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)C(=O)O)NC(=O)OC2=O

Technology Process of 2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-8-carboxylic acid

There total 3 articles about 2,4-Dioxo-1,4-dihydro-2H-3,1-benzoxazine-8-carboxylic acid 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: 98.0%

bis(trichloromethyl) carbonate (32315-10-9) + 2-aminoisophthalic acid (39622-79-2) → 8-carboxyisatoic anhydride (167902-99-0)

Guidance literature:

In tetrahydrofuran; at 40 - 50 ℃; for 3h;

Reference yield: 90.0%

2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-8-carboxamide → 8-carboxyisatoic anhydride (167902-99-0)

Guidance literature:

With sulfuric acid; sodium nitrite; at 27 ℃; for 3h;

DOI:10.1021/acs.joc.1c02036

Reference yield:

isatin-7-carboxylic acid (25128-35-2) → 8-carboxyisatoic anhydride (167902-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; sodium azide; water / 2 h / 27 °C

2: sulfuric acid; sodium nitrite / 3 h / 27 °C

With sodium azide; sulfuric acid; water; sodium nitrite;

DOI:10.1021/acs.joc.1c02036

upstream raw materials:

bis(trichloromethyl) carbonate

2-aminoisophthalic acid

isatin-7-carboxylic acid

Downstream raw materials:

2-amino-3-(N-methylcarbamoyl)benzoic acid

2-amino-3-(N-ethylcarbamoyl)benzoic acid