6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione

Base Information

• Chemical Name: 6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione
• CAS No.: 14529-12-5
• Molecular Formula: C9H6ClNO3
• Molecular Weight: 211.605
• European Community (EC) Number: 238-551-6
• DSSTox Substance ID: DTXSID90162964
• Nikkaji Number: J67.821J
• Wikidata: Q72454132
• ChEMBL ID: CHEMBL2146654
• Mol file: 14529-12-5.mol

Synonyms:14529-12-5;6-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione;5-CHLORO-N-METHYLISATOIC ANHYDRIDE;6-chloro-1-methyl-3,1-benzoxazine-2,4-dione;6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione;6-Chloro-N-methyl IA;BRN 0613893;EINECS 238-551-6;2H-3,1-BENZOXAZINE-2,4(1H)-DIONE, 6-CHLORO-1-METHYL-;6-chloro-1-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione;N-methyl-5-chloroisatoic anhydride;SCHEMBL607256;CHEMBL2146654;DTXSID90162964;AMY23289;5-Chloro-N-methyl Isatoic anhydride;AKOS002664950;LS-41763;FT-0645822;EN300-235715;F87126;6-chloranyl-1-methyl-3,1-benzoxazine-2,4-dione;A808345;A1-47366;F1943-0050

Chemical Property of 6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione

Chemical Property:

• Vapor Pressure: 5.57E-05mmHg at 25°C
• Melting Point: 113 °C
• Refractive Index: 1.597
• Boiling Point: 346.94 °C at 760 mmHg
• PKA: -3.11±0.20(Predicted)
• Flash Point: 163.623 °C
• PSA: 52.21000
• Density: 1.477 g/cm³
• LogP: 1.14510
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 211.0036207
• Heavy Atom Count: 14
• Complexity: 281

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C=C(C=C2)Cl)C(=O)OC1=O

Technology Process of 6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione

There total 13 articles about 6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-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: 90.0%

5-Chloroisatoic anhydride (4743-17-3) + methyl iodide (74-88-4) → 6-chloro-N-methylisatoic anhydride (14529-12-5)

Guidance literature:

In ice-water; ISOPROPYLAMIDE;

Reference yield: 78.0%

carbon monoxide (201230-82-2) + N-methyl(p-chloroaniline) (932-96-7) → 6-chloro-N-methylisatoic anhydride (14529-12-5)

Guidance literature:

With oxygen; copper diacetate; palladium diacetate; potassium iodide; Trimethylacetic acid; In acetonitrile; at 60 ℃; under 760.051 Torr; regioselective reaction;

DOI:10.1021/ja308976x

Reference yield: 72.0%

5-Chloroisatoic anhydride (4743-17-3) + methyl bromide (74-83-9) → 6-chloro-N-methylisatoic anhydride (14529-12-5)

Guidance literature:

5-Chloroisatoic anhydride; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

methyl bromide; In N,N-dimethyl-formamide; for 18h;

DOI:10.1016/j.bmc.2012.08.049

upstream raw materials:

chloroformic acid ethyl ester

dimethyl sulfate

5-chloroanthranilic acid

5-Chloroisatoic anhydride

Downstream raw materials:

C₁₆H₁₉ClN₂O₂

C₁₅H₂₁ClN₂O

Refernces

• 1、 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.
• 2、 Wang, Shoucai,Li, Xuan,Zang, Jiawang,Liu, Meichen,Zhang, Siyu,Jiang, Guangbin,Ji, Fanghua. "Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides". . p. 2672 - 2679. Retrieved 2020/02/04.