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

Base Information

• Chemical Name: 6-Fluoro-2H-1,3-benzoxazine-2,4(3H)-dione
• CAS No.: 134792-45-3
• Molecular Formula: C₈H₄FNO₃
• Molecular Weight: 181.123
• DSSTox Substance ID: DTXSID20602328
• Wikidata: Q82499331
• Mol file: 134792-45-3.mol

Synonyms:134792-45-3;6-fluoro-1,3-benzoxazine-2,4-dione;6-Fluoro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione;6-FLUORO-2H-1,3-BENZOXAZINE-2,4(3H)-DIONE;6-fluoro-3,4-dihydro-2H-1,3-benzoxazine-2,4-dione;2H-1,3-Benzoxazine-2,4(3H)-dione,6-fluoro-;SCHEMBL6590435;SCHEMBL9268687;DTXSID20602328;SLGAPWSWRLDIMS-UHFFFAOYSA-N;AKOS033969130;CS-0138303;6-fluoro-2H-1,3-benzoxazine-2,4(1H)-dione;EN300-313196;A806842;A1-27290;Z1262693326

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

Chemical Property:

• Melting Point: 192-196℃
• Boiling Point: °Cat760mmHg
• PKA: 9.71±0.20(Predicted)
• Flash Point: °C
• PSA: 63.07000
• Density: 1.502g/cm³
• LogP: 0.62040
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO
• 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:

99%, ^*data from raw suppliers

6-Fluoroisatoicanhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1F)C(=O)NC(=O)O2
• Uses: 5-Fluoroisatoic Anhydride is a versatile pharmaceutical intermediate used in the preparation of insulin secretagogues, HCV polymerase inhibitors, anxiolytic agents and other bioactive compounds.

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

There total 4 articles about 6-Fluoro-2H-1,3-benzoxazine-2,4(3H)-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: 99.0%

chloroformic acid ethyl ester (541-41-3) + 5-fluoro-2-hydroxybenzamide (56874-97-6) → 6-fluoro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (134792-45-3)

Guidance literature:

With pyridine; In acetonitrile; at 5 - 120 ℃; for 0.5h;

DOI:10.1002/ejoc.201501515

Reference yield: 55.0%

5-fluoro-2-hydroxybenzamide (56874-97-6) + 1,1'-carbonyldiimidazole (530-62-1) → 6-fluoro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (134792-45-3)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 14h;

Reference yield:

methyl 5-fluoro-2-hydroxybenzoate (391-92-4) → 6-fluoro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (134792-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia / methanol / 10 h / 50 °C / Autoclave

2: tetrahydrofuran / 14 h / 0 - 20 °C

With ammonia; In tetrahydrofuran; methanol;

upstream raw materials:

methyl 5-fluoro-2-hydroxybenzoate

5-fluoro-2-hydroxybenzoic acid

5-fluoro-2-hydroxybenzamide

1,1'-carbonyldiimidazole

Downstream raw materials:

6-fluoro-3,4-dihydroquinazolin-4-one

10-(3-benzyl-1,2,4-oxadiazol-5-yl)-3-fluoro-9H-imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine

4-fluoro-2-(1H-1,2,4-triazol-3-yl)aniline