6-Fluoroisatoic anhydride

Base Information

• Chemical Name: 6-Fluoroisatoic anhydride
• CAS No.: 78755-94-9
• Molecular Formula: C8H4FNO3
• Molecular Weight: 181.123
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00382419
• Wikidata: Q72473782
• Mol file: 78755-94-9.mol

Synonyms:78755-94-9;6-Fluoroisatoic anhydride;5-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione;5-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione;5-fluoro-1H-3,1-benzoxazine-2,4-dione;5-fluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione;6-fluoroisatoicanhydride;5-fluorobenzo[d][1,3]oxazine-2,4-dione;6-fluoro isatoic anhydride;6-fluoroisatoic acid anhydride;SCHEMBL1203402;DTXSID00382419;VAAIGNBVENPUEI-UHFFFAOYSA-N;MFCD00112979;AKOS005070888;AB13979;CS-0045056;FT-0653182;EN300-200751;6W-0030;J-018665;Z1094720984

Chemical Property of 6-Fluoroisatoic anhydride

Chemical Property:

• Melting Point: 230℃
• PKA: 9.75±0.20(Predicted)
• PSA: 63.07000
• Density: 1.502 g/cm³
• LogP: 0.62040
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 181.01752115
• Heavy Atom Count: 13
• Complexity: 256

Purity/Quality:

98% ^*data from raw suppliers

5-fluoro-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: C1=CC2=C(C(=C1)F)C(=O)OC(=O)N2

Technology Process of 6-Fluoroisatoic anhydride

There total 6 articles about 6-Fluoroisatoic 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) + 2-amino-6-fluorobenzoic acid (434-76-4) → 5-fluoro-2H-benzo[d][1,3]-oxazine-2,4(1H)-dione (78755-94-9)

Guidance literature:

In tetrahydrofuran; at 50 ℃;

DOI:10.1021/jm050855s

Reference yield: 94.0%

phosgene (75-44-5) + 2-amino-6-fluorobenzoic acid (434-76-4) → 5-fluoro-2H-benzo[d][1,3]-oxazine-2,4(1H)-dione (78755-94-9)

Guidance literature:

In toluene; at 100 ℃;

Reference yield:

3-fluorophthalic anhydride (652-39-1) → 8-fluoro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione (174463-53-7) + 5-fluoro-2H-benzo[d][1,3]-oxazine-2,4(1H)-dione (78755-94-9)

Guidance literature:

With trimethylsilylazide; In chloroform; for 3.5h; Title compound not separated from byproducts; Heating;

DOI:10.1021/jm950551d

upstream raw materials:

3-fluorophthalic anhydride

2-amino-6-fluorobenzoic acid

trichloromethyl chloroformate

phosgene

Downstream raw materials:

2-amino-6-fluoro-N-methylbenzamide

2-amino-6-fluoro-N′-isopropylbenzamide

2-amino-6-fluorophenyl(4-methylpiperazin-1-yl)methanone

Refernces

• 1、 Khalifa, Muhammad M.,Philkhana, Satish Chandra,Golden, Jennifer E.. "Synthesis of Ring-Fused, N-Substituted 4-Quinolinones Using p Ka-Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam". . p. 464 - 481. Retrieved 2019/12/24.
• 2、 Guo, Ran,Lv, Ning,Zhang, Fa-Guang,Ma, Jun-An. "Zinc-Mediated Mannich-Type Reaction of 2,2,2-Trifluorodiazoethane with Imines: Access to β-CF3-Amines". supporting information. p. 6994 - 6997. Retrieved 2018/11/23.