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:

2-Methylamino-N-morpholin-4-yl-benzamide

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

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

N-(2-methylaminobenzoyl)indole

Refernces

ATTACHMENT OF THE ANTHRAMYCIN ACRYLAMIDE SIDE CHAIN BY THE PALLADIUM CATALYZED COUPLING REACTION OF A VINYL TRFLATE

10.1016/S0040-4039(00)96916-8

The research focuses on the attachment of the anthramycin acrylamide side chain to the pyrrolo(1,4)benzodiazepine structure via a palladium-catalyzed coupling reaction of a vinyl triflate. Anthramycin, an antitumor antibiotic, has a complex synthesis process. The study explores a more efficient route by converting the 2-keto group in the pyrrolo ring to a vinyl triflate and then coupling it with various reagents. Key chemicals involved include N-methyl isatoic anhydride, L-hydroxyproline, triflic anhydride, pyridine, tributylvinylstannane, ethyl acrylate, and palladium catalysts such as (Ph3P)2Pd and PdCl2. The methodology provides a convenient procedure for constructing anthramycin derivatives, offering a rapid entry into the pyrrolo(1,4)benzodiazepine structure with the desired side chain.

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