5-Chloroisatoic anhydride

Base Information

• Chemical Name: 5-Chloroisatoic anhydride
• CAS No.: 4743-17-3
• Molecular Formula: C8H4ClNO3
• Molecular Weight: 197.578
• Hs Code.: 2934999090
• European Community (EC) Number: 225-255-7
• NSC Number: 139890,75847
• DSSTox Substance ID: DTXSID3063592
• Nikkaji Number: J236.703C
• Wikidata: Q72452743
• Mol file: 4743-17-3.mol

Synonyms:5-Chloroisatoic anhydride;4743-17-3;6-chloro-1h-benzo[d][1,3]oxazine-2,4-dione;5-chloro-isatoic anhydride;2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-;6-chloro-1H-3,1-benzoxazine-2,4-dione;C8H4ClNO3;5-chloro isatoic anhydride;6-Chloro-4H-3,1-benzoxazine-2,4(1H)-dione;NSC 75847;6-Chloro isatinic anhydride;6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione;EINECS 225-255-7;MFCD00006701;6-Chloro-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione;6-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione;NSC 139890;AI3-61136;2H-3,4(1H)-dione, 6-chloro-;5-chloroisatonic anhydride;6-chloro-1H-benzo[d]1,3-oxazine-2,4-dione;SCHEMBL62706;DTXSID3063592;5-Chloroisatoic anhydride, 97%;NSC75847;AM1021;BBL009787;NSC-75847;NSC139890;STK913991;AKOS000271184;AC-9247;CS-W010558;FS-1284;NSC-139890;AC-14653;SY025838;A7268;C2743;FT-0635421;6-chloro-1hbenzo[d][1,3]oxazine-2,4-dione;EN300-255835;6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione #;Q-102085;6-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione;6-Chloro-1,2-dihydro -4H-3,1-benzoxazine-2,4-dione;F0074-0091

Chemical Property of 5-Chloroisatoic anhydride

Chemical Property:

• Melting Point: 300 °C (dec.)(lit.)
• PKA: 9.76±0.20(Predicted)
• PSA: 63.07000
• Density: 1.54 g/cm³
• LogP: 1.13470
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 196.9879707
• Heavy Atom Count: 13
• Complexity: 256

Purity/Quality:

99% ^*data from raw suppliers

5-Chloroisatoic anhydride ^*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: C1=CC2=C(C=C1Cl)C(=O)OC(=O)N2
• Uses: 5-Chloroisatoic Anhydride was used as a reagent in the synthesis of 2-acetamidobenzamides bearing the 2-phenoxy functionality which display antiproliferative activity against certain tumor cell lines. Also used in the preparation of inhibitors of delta-5 desaturase.

Technology Process of 5-Chloroisatoic anhydride

There total 21 articles about 5-Chloroisatoic 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: 99.0%

carbon monoxide (201230-82-2) + 5-chloroanthranilic acid (635-21-2) → 5-Chloroisatoic anhydride (4743-17-3)

Guidance literature:

With oxygen; copper diacetate; palladium diacetate; potassium iodide; In acetonitrile; at 60 ℃; for 4h; under 760.051 Torr;

DOI:10.1021/jo500417u

Reference yield: 98.0%

bis(trichloromethyl) carbonate (32315-10-9) + 5-chloroanthranilic acid (635-21-2) → 5-Chloroisatoic anhydride (4743-17-3)

Guidance literature:

In 1,2-dichloro-ethane; for 4h; Reflux;

Reference yield: 97.0%

2-chloro-6-aminobenzoic acid (2148-56-3) + acetyl chloride (75-36-5) → 5-Chloroisatoic anhydride (4743-17-3)

Guidance literature:

2-chloro-6-aminobenzoic acid; With chloroformic acid ethyl ester; In 1,4-dioxane; for 1h; Heating / reflux;

acetyl chloride; In 1,4-dioxane; at 50 ℃; for 10h;

upstream raw materials:

5-chloroindole 2,3-dione

5-Chloro-2-isocyanatobenzoyl chloride

phenylmagnesium bromide

phosgene

Downstream raw materials:

6-chloro-8-nitro-1H-benz[d][1,3]oxazine-2,4-dione

2-amino-5-chloro-3-nitrobenzoic acid

2-Amino-5-chlor-N²-phenyl-benzoesaeure-hydrazid

2-Amino-5-chlor-N²-(4-nitrophenyl)-benzoesaeurehydrazid

Refernces

• 1、 Feng, Bin,Zhu, Yingli,Wu, Jiaxin,Huang, Xueyan,Song, Rong,Huang, Liu,Feng, Xueping,Zeng, Wenbin. "Monitoring intracellular pH fluctuation with an excited-state intramolecular proton transfer-based ratiometric fluorescent sensor". supporting information. p. 3057 - 3060. Retrieved 2021/04/12.
• 2、 -. "APPLICATION OF N-BENZYL TRYPTANTHRIN DERIVATIVE AS TRYPTOPHAN DIOXYGENASE (TDO) INHIBITOR". Paragraph 0102; 0105. . Retrieved 2020/04/24.