4-Fluoro-3-nitrobenzoic acid

Base Information

• Chemical Name: 4-Fluoro-3-nitrobenzoic acid
• CAS No.: 453-71-4
• Molecular Formula: C7H4FNO4
• Molecular Weight: 185.111
• Hs Code.: 29163990
• European Community (EC) Number: 207-221-3
• NSC Number: 10311
• UNII: 4XU69FAU2V
• DSSTox Substance ID: DTXSID30196465
• Nikkaji Number: J196.154C,J374.726C
• Wikidata: Q72475252
• Mol file: 453-71-4.mol

Synonyms:4-fluoro-3-nitrobenzoic acid

Chemical Property of 4-Fluoro-3-nitrobenzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Melting Point: 120-126 °C
• Refractive Index: 1.588
• Boiling Point: 356.9 °C at 760 mmHg
• PKA: 3.54±0.10(Predicted)
• Flash Point: 169.6 °C
• PSA: 83.12000
• Density: 1.568 g/cm³
• LogP: 1.95530
• Storage Temp.: Refrigerator
• Solubility.: 95% ethanol: soluble50mg/mL, clear, light yellow
• Water Solubility.: insoluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 185.01243577
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

4-Fluoro-3-nitrobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(=O)O)[N+](=O)[O-])F
• Uses: 4-Fluoro-3-nitrobenzoic acid was used:as starting reagent in the preparation of novel benzimidazoles having antimycobacterial activityin preparation of series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structurein preparation of bis(heterocyclic) skeletal precursors for the Pictet-Spengler reactionin solid-phase synthesis of trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4(3H,10H)-diones

Technology Process of 4-Fluoro-3-nitrobenzoic acid

There total 12 articles about 4-Fluoro-3-nitrobenzoic acid 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%

4-Fluorobenzoic acid (456-22-4) → 3-nitro-4-fluorobenzoic acid (453-71-4)

Guidance literature:

With sulfuric acid; potassium nitrate; at 20 ℃;

Reference yield: 70.0%

trimethylsilylazide (4648-54-8) + 4-fluoro-3-nitrobenzoyl chloride (400-94-2) → 3-nitro-4-fluorobenzoic acid (453-71-4) + 1-(4-fluoro-5-nitrophenyl)-1,4-dihydro-5H-tetrazol-5-one (1309832-87-8)

Guidance literature:

at 20 - 90 ℃; Inert atmosphere;

DOI:10.1039/c6ob01644h

Reference yield: 52.0%

4-fluoro-3-nitrobenzonitrile (1009-35-4) → 3-nitro-4-fluorobenzoic acid (453-71-4)

Guidance literature:

With sulfuric acid; at 120 ℃; for 8h; Sealed tube;

upstream raw materials:

4-Fluorobenzoic acid

4-fluorobenzaldehyde

nitric acid

p-fluorotoluene

Downstream raw materials:

3-nitro-4-o-toluidino-benzoic acid

Refernces

• 1、 Kikuchi, Mariko,Kurotani, Reiko,Konno, Hiroyuki. "Synthesis of a secretoglobin 3A2 type C (98–139) fragment by Dawson's native chemical ligation". supporting information. p. 4145 - 4148. Retrieved 2017/09/29.
• 2、 Duncton, Matthew A. J.,Singh, Rajinder. "A one-pot synthesis of tetrazolones from acid chlorides: Understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs". supporting information. p. 9338 - 9342. Retrieved 2016/10/13.