Isatoic anhydride

Base Information

• Chemical Name: Isatoic anhydride
• CAS No.: 118-48-9
• Deprecated CAS: 32779-11-6
• Molecular Formula: C8H5NO3
• Molecular Weight: 179.132
• Hs Code.: 29349990
• European Community (EC) Number: 204-255-0
• NSC Number: 104662,29555
• UNII: R8TFA74Y4U
• DSSTox Substance ID: DTXSID6026955
• Nikkaji Number: J5.526C
• Wikipedia: Isatoic_anhydride
• Wikidata: Q11286492
• Metabolomics Workbench ID: 152737
• ChEMBL ID: CHEMBL346059
• Mol file: 118-48-9.mol

Synonyms:isatoic anhydride

Chemical Property of Isatoic anhydride

Chemical Property:

• Appearance/Colour: beige to brown powder
• Melting Point: 233 °C (dec.)(lit.)
• Refractive Index: 1.585
• Boiling Point: 290.19°C (rough estimate)
• PKA: 11.06±0.20(Predicted)
• Flash Point: 308 °C
• PSA: 63.07000
• Density: 1.402 g/cm³
• LogP: 0.48130
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: 0.3g/l
• Water Solubility.: decomposes
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 163.026943022
• Heavy Atom Count: 12
• Complexity: 226

Purity/Quality:

99% ^*data from raw suppliers

Isatoic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 24-26-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)OC(=O)N2
• Uses: Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.

Technology Process of Isatoic anhydride

There total 89 articles about Isatoic 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: 100.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → isatoic anhydride (118-48-9)

Guidance literature:

In acetonitrile; at 20 ℃; for 24h; Inert atmosphere; Photolysis;

Reference yield: 100.0%

bis(trichloromethyl) carbonate (32315-10-9) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → isatoic anhydride (118-48-9)

Guidance literature:

In tetrahydrofuran; at 45 ℃; for 12h;

DOI:10.1016/j.tet.2016.03.059

Reference yield: 99.0%

carbon dioxide (124-38-9,18923-20-1) + 2-azidobenzoic acid (31162-13-7) → isatoic anhydride (118-48-9)

Guidance literature:

With cetyltrimethylammonim bromide; triphenylphosphine; In acetonitrile; at 60 ℃; for 24h; under 760.051 Torr; Solvent; Temperature;

upstream raw materials:

phthalic anhydride

4-oxo-4H-benzo[d][1,3]oxazine-2-carbonitrile

ethanol

anthranil

Downstream raw materials:

N-methoxycarbonyl-anthranilic acid

methyl 2-((methoxycarbonyl)amino)benzoate

anthranilic acid

2-carbomethoxyaniline

Refernces

• 1、 Nelson, Amber C.,Kalinowski, Emily S.,Czerniecki, Nikolas J.,Jacobson, Taylor L.,Grundt, Peter. "Is the 2,3-carbon-carbon bond of indole really inert to oxidative cleavage by Oxone?-Synthesis of isatoic anhydrides from indoles". . p. 7455 - 7457. Retrieved 2013.
• 2、 Huang, Jun-Min,Chen, Hui,Chen, Ru-Yu. "An unusual addition and ring-closure reaction of 1-(2-bromoethyl)-2,3-dihydro-3-propyl-1,3,2-benzo-diazaphosphorin-4(1H)-one 2-oxide with carbon disulfide for a new and convenient synthesis of the fused phosphorus heterocyclic compound". . p. 2215 - 2225. Retrieved 2002.
• 3、 Jiang, Shi-Fen,Xu, Cheng,Zhou, Zhi-Wen,Zhang, Qin,Wen, Xiao-Hui,Jia, Feng-Cheng,Wu, An-Xin. "Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes". . p. 4231 - 4234. Retrieved 2018.
• 4、 Sharafian, Shirin,Hossaini, Zinatossadat,Rostami-Charati, Faramarz,Khalilzadeh, Mohammad A.. "Green synthesis of novel phosphonate derivatives using ultrasonic irradiation". . p. 1283 - 1291. Retrieved 2020.
• 5、 Chen, Xingyu,Xia, Fei,Zhao, Yifan,Ma, Ji,Ma, Yue,Zhang, Dong,Yang, Lan,Sun, Peng. "TBHP-Mediated Oxidative Decarboxylative Cyclization in Water: Direct and Sustainable Access to Anti-malarial Polycyclic Fused Quinazolinones and Rutaecarpine". . p. 1239 - 1244. Retrieved 2020.
• 6、 Nelson, Amber C.,Kalinowski, Emily S.,Jacobson, Taylor L.,Grundt, Peter. "Formation of tryptanthrin compounds upon Oxone-induced dimerization of indole-3-carbaldehydes". . p. 6804 - 6806. Retrieved 2013.
• 7、 -. "Preparation method of 4(3H)-quinazolinone compound". Paragraph 0007; 0029-0042. . Retrieved 2021/05/01.
• 8、 -. "MODIFIED PROTEINS AND PROTEIN DEGRADERS". Paragraph 00455; 00458; 00459. . Retrieved 2021/12/08.