N-Methylisatoic anhydride

Base Information

• Chemical Name: N-Methylisatoic anhydride
• CAS No.: 10328-92-4
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.159
• Hs Code.: 2934999090
• European Community (EC) Number: 233-714-8
• NSC Number: 76087
• UNII: 7SWE4B4CY2
• DSSTox Substance ID: DTXSID8065036
• Nikkaji Number: J67.822H
• Wikidata: Q27126419
• Metabolomics Workbench ID: 60376
• ChEMBL ID: CHEMBL1903371
• Mol file: 10328-92-4.mol

Synonyms:N-methylisatoic anhydride

Chemical Property of N-Methylisatoic anhydride

Chemical Property:

• Appearance/Colour: brownish chunks
• Vapor Pressure: 0.00135mmHg at 25°C
• Melting Point: 165 ºC (dec.)(lit.)
• Refractive Index: 1.583
• Boiling Point: 297.5 ºC at 760 mmHg
• PKA: -2.24±0.20(Predicted)
• Flash Point: 133.7 ºC
• PSA: 52.21000
• Density: 1.348 g/cm³
• LogP: 0.49170
• Storage Temp.: -20°C
• Sensitive.: Moisture Sensitive
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=O)OC1=O
• Uses: N-Methylisatoic anhydride is a 2'-OH selective acylation agent of RNAs, and is widely used for resolving secondary RNA structures using the SHAPE (Selective 2'-Hydroxyl Acylation Analyzed by Primer Extension) technology.

Technology Process of N-Methylisatoic anhydride

There total 36 articles about N-Methylisatoic anhydride 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: 97.0%

bis(trichloromethyl) carbonate (32315-10-9) + N-Methylanthranilic acid (119-68-6) → N-Methylisatoic anhydride (10328-92-4)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 2h; Solvent;

Reference yield: 92.0%

carbon dioxide (124-38-9,18923-20-1) + carbon monoxide (201230-82-2) + N-methyl-2-iodoaniline (57056-93-6) → N-Methylisatoic anhydride (10328-92-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium acetate; In tetrahydrofuran; at 60 ℃; for 16h;

DOI:10.1021/acscatal.7b03000

Reference yield: 89.0%

isatoic anhydride (118-48-9) + methyl iodide (74-88-4) → N-Methylisatoic anhydride (10328-92-4)

Guidance literature:

With N,N-dimethyl acetamide; N-ethyl-N,N-diisopropylamine; at 40 ℃; for 24h;

DOI:10.3762/bjoc.12.221

upstream raw materials:

N-methoxycarbonyl-N-methyl-anthranilic acid

N-carbethoxy-N-methylanthranilic acid

N-Methylanthranilic acid

chloroformic acid ethyl ester

Downstream raw materials:

dihydro-3-(2-methylaminobenzoyl)-2(3H)-furanone

5,5-Dimethyl-3-(2-methylamino-benzoyl)-dihydro-furan-2-one

2-(2-methylamino)phenyl-2-propanol

β-D-3'-O-(N-methylanthraniloyl)-2'-deoxycytidine

Refernces

• 1、 Banu, Saleha,Bollu, Rajitha,Bantu, Rajashaker,Nagarapu, Lingaiah,Polepalli, Sowjanya,Jain, Nishant,Vangala, Radhika,Manga, Vijjulatha. "Design, synthesis and docking studies of novel 1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamide derivatives as a potential anti-proliferative agents". . p. 400 - 410. Retrieved 2017.
• 2、 Tomassoli, Isabelle,Herlem, Guillaume,Picaud, Fabien,Benchekroun, Mohamed,Bautista-Aguilera, Oscar M.,Luzet, Vincent,Jimeno, María-Luisa,Gharbi, Tijani,Refouvelet, Bernard,Ismaili, Lhassane. "Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones". . p. 1069 - 1079. Retrieved 2016.
• 3、 Banu, Saleha,Bollu, Rajitha,Nagarapu, Lingaiah,Nanubolu, Jagadeesh Babu,Yogeswari, Perumal,Sriram, Dharmarajan,Gunda, Shravan Kumar,Vardhan, Divyasphoorthi. "Design, Synthesis, and in vitro antitubercular activity of 1,2,3-triazolyl-dihydroquinoline derivatives". . p. 1315 - 1323. Retrieved 2018.
• 4、 Martínez Suárez, Jaime F.,Caram, José A.,Echeverriá, Gustavo. A.,Piro, Oscar E.,Gennaro, Ana. M.,Mirífico, Mariá. V.. "Electrosynthesis of N-methylisatin". . p. 6879 - 6885. Retrieved 2019.
• 5、 Ding, Qianqian,Fan, Xuesen,Wang, Jinjun,Yang, Jingyi,Zhang, Guisheng,Zhang, Xiaopeng. "Pd(ii)-Catalyzed [4 + 1 + 1] cycloaddition of simple: O -aminobenzoic acids, CO and amines: Direct and versatile synthesis of diverse N -substituted quinazoline-2,4(1 H,3 H)-diones". . p. 526 - 535. Retrieved 2021/01/28.
• 6、 Andryianau, Gleb,Bartoszewicz, Agnieszka,Czestkowski, Wojciech,Dymek, Barbara,Dzwonek, Karolina,Golab, Jakub,Golebiowski, Adam,Gruza, Mariusz,Koralewski, Robert,Kowalski, Michal,Matyszewski, Krzysztof,Mazur, Marzena,Niedziejko, Piotr,Olczak, Jacek,Olejniczak, Sylwia,Piotrowicz, Michal C.,Pluta, Elzbieta,Rajkiewicz, Adam A.,Rymaszewska, Aleksandra,Salamon, Magdalena,Sklepkiewicz, Piotr L.,Stefaniak, Filip,Welzer, Mikolaj,Zagozdzon, Agnieszka. "Benzoxazepine-Derived Selective, Orally Bioavailable Inhibitor of Human Acidic Mammalian Chitinase". supporting information. p. 1228 - 1235. Retrieved 2020/07/03.