4-Bromoisatoic anhydride

Base Information

• Chemical Name: 4-Bromoisatoic anhydride
• CAS No.: 76561-16-5
• Molecular Formula: C8H4BrNO3
• Molecular Weight: 242.029
• Hs Code.: 2934999090
• European Community (EC) Number: 838-561-6
• DSSTox Substance ID: DTXSID80467990
• Nikkaji Number: J1.262.632K
• Wikidata: Q72445792
• Mol file: 76561-16-5.mol

Synonyms:4-Bromoisatoic anhydride;76561-16-5;7-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione;7-bromo-1H-3,1-benzoxazine-2,4-dione;4-Bromo-isatoic anhydride;7-Bromo-2H-3,1-benzoxazine-2,4(1H)-dione;4-Bromoisatoicanhydride;MFCD11113115;7-BROMO-2,4-DIHYDRO-1H-3,1-BENZOXAZINE-2,4-DIONE;2H-3,1-Benzoxazine-2,4(1H)-dione, 7-bromo-;SCHEMBL2382755;DTXSID80467990;PDGHWWQDMPEMKS-UHFFFAOYSA-N;AKOS015900474;AC-9611;FS-3648;BL000123;SY025843;CS-0030378;FT-0645210;7-bromo-1H-benzo[d]-1,3-oxazine-2,4-dione;A26551;EN300-189812;J-519100

Chemical Property of 4-Bromoisatoic anhydride

Chemical Property:

• Refractive Index: 1.623
• PKA: 9.95±0.20(Predicted)
• PSA: 63.07000
• Density: 1.826 g/cm³
• LogP: 1.24380
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 240.93746
• Heavy Atom Count: 13
• Complexity: 256

Purity/Quality:

99% ^*data from raw suppliers

4-Bromoisatoicanhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)NC(=O)OC2=O

Technology Process of 4-Bromoisatoic anhydride

There total 8 articles about 4-Bromoisatoic 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%

bis(trichloromethyl) carbonate (32315-10-9) + 2-amino-4-bromobenzoic acid (20776-50-5) → 7-bromo-1,2-dihydro-3,1-4H-benzoxazine-2,4-dione (76561-16-5)

Guidance literature:

In 1,4-dioxane; at 0 ℃; for 16h; Inert atmosphere; Reflux;

Reference yield: 78.0%

6-bromoisatin (6326-79-0) → 7-bromo-1,2-dihydro-3,1-4H-benzoxazine-2,4-dione (76561-16-5)

Guidance literature:

With diphenyl diselenide; dihydrogen peroxide; In N,N-dimethyl-formamide; acetonitrile; at 25 ℃; for 8h; Schlenk technique; Green chemistry;

DOI:10.1039/c5cy01030f

Reference yield:

4-bromo-2-((tert-butoxycarbonyl)amino)benzoic acid (1183031-46-0) → 7-bromo-1,2-dihydro-3,1-4H-benzoxazine-2,4-dione (76561-16-5)

Guidance literature:

4-bromo-2-((tert-butoxycarbonyl)amino)benzoic acid; With 2-chloro-1-methyl-pyridinium iodide; In acetonitrile; at 20 ℃; for 0.166667h;

With hydrogenchloride; In water; acetonitrile;

DOI:10.1016/j.tetlet.2013.10.034

upstream raw materials:

(E)-N-(3-bromophenyl)-2-(hydroxyimino)acetamide

6-bromoisatin

phosgene

2-amino-4-bromobenzoic acid

Downstream raw materials:

N-methyl-2-amino-4-bromobenzamide

4-bromo-2-(3-methoxypropanamido)-N-methylbenzamide

Refernces

• 1、 Chen, Xiulei,Zhou, Zhen,Li, Zhong,Xu, Xiaoyong. "Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita". . p. 194 - 200. Retrieved 2019/09/13.
• 2、 Jentsch, Nicholas G.,Hume, Jared D.,Crull, Emily B.,Beauti, Samer M.,Pham, Amy H.,Pigza, Julie A.,Kessl, Jacques J.,Donahue, Matthew G.. "Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: Preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives". . p. 2529 - 2536. Retrieved 2018/10/21.