8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Base Information

• Chemical Name: 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione
• CAS No.: 34954-65-9
• Molecular Formula: C9H7NO4
• Molecular Weight: 193.159
• Hs Code.: 2934999090
• European Community (EC) Number: 676-016-2
• DSSTox Substance ID: DTXSID10441708
• Nikkaji Number: J2.774.027H
• Wikidata: Q82258599
• Mol file: 34954-65-9.mol

Synonyms:34954-65-9;3-Methoxy-isatoic anhydride;8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione;3-methoxyisatoic anhydride;8-methoxy-1H-3,1-benzoxazine-2,4-dione;8-methoxy-2H-benzo[d][1,3]oxazine-2,4(1H)-dione;8-methoxyisatoic anhydride;8-METHOXY-2,4-DIHYDRO-1H-3,1-BENZOXAZINE-2,4-DIONE;3-methoxy isatoic anhydride;SCHEMBL1515079;2H-3,1-BENZOXAZINE-2,4(1H)-DIONE, 8-METHOXY-;DTXSID10441708;ZPTOZGCACQWXJX-UHFFFAOYSA-N;MFCD04114326;AKOS012410257;AB18079;AC-6601;AS-38031;A6137;CS-0072614;FT-0687253;EN300-265846;8-Methoxy-2H-3,1-benzooxazine-2,4(1H)-dione;Q-102103;F2167-2355;Z1094719212

Chemical Property of 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Chemical Property:

• Melting Point: 255-260 °C
• Refractive Index: 1.565
• PKA: 10.42±0.20(Predicted)
• PSA: 63.07000
• Density: 1.376 g/cm³
• LogP: 0.78970
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 193.03750770
• Heavy Atom Count: 14
• Complexity: 266

Purity/Quality:

98%min ^*data from raw suppliers

3-MethoxyisatoicAnhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1NC(=O)OC2=O
• Uses: 3-Methoxyisatoic Anhydride is used as a reagent in the synthesis of Tryptanthrin (T947000) and its analogs as antitubercular agents. 3-Methoxyisatoic Anhydride is also used in the preparation of quinazolin-2-ylamino-quinazolin-4-ols as non-nucleoside inhibitors of bacterial DNA polymerase III.

Technology Process of 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

There total 8 articles about 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione 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: 94.0%

phosgene (75-44-5) + 2-amino-3-methoxybenzoic acid (3177-80-8) → 3-methoxyisatoic anhydride (34954-65-9)

Guidance literature:

In 1,4-dioxane; benzene; Ambient temperature;

DOI:10.1021/jm00138a019

Reference yield: 91.0%

2-amino-3-methoxybenzoic acid (3177-80-8) + bis(trichloromethyl) carbonate (32315-10-9) → 3-methoxyisatoic anhydride (34954-65-9)

Guidance literature:

In tetrahydrofuran; for 3h; Reflux; Inert atmosphere;

Reference yield: 73.0%

2-amino-3-methoxybenzoic acid (3177-80-8) + trifluoroacetyl chloride (76-02-8) → 3-methoxyisatoic anhydride (34954-65-9)

Guidance literature:

In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;

DOI:10.1039/c5md00062a

upstream raw materials:

phosgene

2-amino-3-methoxybenzoic acid

trichloromethyl chloroformate

3-methoxyphthalic anhydride

Downstream raw materials:

2-(3-Methoxy-2-methylamino-benzoyl)-5-methyl-hex-4-enoic acid ethyl ester

2-amino-3-methoxybenzoic acid

2-amino-N-(4-bromo-phenyl)-3-methoxy-benzamide

2-amino-N-(4-sec-butyl-phenyl)-3-methoxy-benzamide

Refernces

• 1、 Chen, Xiulei,Zhou, Zhen,Li, Zhong,Xu, Xiaoyong. "Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita". . p. 194 - 200. Retrieved 2019/09/13.
• 2、 -. "Quinazoline dione derivatives and preparation method and application thereof". Paragraph 0322; 0323; 0324. . Retrieved 2017/07/19.