1,2,3-Trifluoro-5-nitrobenzene

Base Information

• Chemical Name: 1,2,3-Trifluoro-5-nitrobenzene
• CAS No.: 66684-58-0
• Molecular Formula: C6H2F3NO2
• Molecular Weight: 177.083
• Hs Code.: 29049090
• European Community (EC) Number: 266-447-0
• DSSTox Substance ID: DTXSID40985261
• Nikkaji Number: J310.134G
• Wikidata: Q72513137
• Mol file: 66684-58-0.mol

Synonyms:3,4,5-Trifluoronitrobenzene;1,2,3-Trifluoro-5-nitrobenzene;66684-58-0;Benzene, 1,2,3-trifluoro-5-nitro-;3,4,5-trifluoro-nitrobenzene;EINECS 266-447-0;MFCD00456803;1,2,3-trifluoro-5-nitro-benzene;3,4,5-trifluronitrobenzene;SCHEMBL239666;3,4,5-trifluoronitro benzene;DTXSID40985261;PTTUMBGORBMNBN-UHFFFAOYSA-N;CS-D1418;3,4,5-Trifluoronitrobenzene, 97%;CX1181;AKOS009158967;AC-7250;AS-12424;SY005361;A1766;AM20050548;FT-0641089;T2357;EN300-45047;Z452557398

Chemical Property of 1,2,3-Trifluoro-5-nitrobenzene

Chemical Property:

• Appearance/Colour: light yellow crystal
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• Boiling Point: 208.6 °C at 760 mmHg
• Flash Point: 79.9 °C
• PSA: 45.82000
• Density: 1.554 g/cm³
• LogP: 2.53530
• Storage Temp.: Room temperature.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 177.00376279
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

3,4,5-Trifluoronitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1F)F)F)[N+](=O)[O-]
• Chemical Composition and Structure: 1,2,3-Trifluoro-5-nitrobenzene, also known as 3,4,5-trifluoronitrobenzene, consists of a benzene ring substituted with three fluorine atoms and one nitro group.
• Uses and Mechanism of Action: Chemical Synthesis: ; Used as a precursor in the synthesis of various target molecules, particularly in Lewis acid-promoted epoxide ring-opening reactions.; ; Photodegradable Antimicrobial Agents: ; Employed in the synthesis of antimicrobial agents through nucleophilic substitution reactions and subsequent modifications.^[1]
• Production Methods: Synthesized through aromatic nucleophilic substitution reactions and Ullmann reactions with appropriate precursors.^[2]
• Analysis Method: Analytical methods for the characterization of 1,2,3-Trifluoro-5-nitrobenzene may include techniques such as spectroscopy, chromatography, and elemental analysis for structural and compositional analysis.
• References: [1] Photodegradable Antimicrobial Agents: Synthesis and Mechanism of Degradation; DOI 10.1021/acs.joc.2c00681; [2] Effects of electron-accepting substituents on the fluorescence of oxygen-bridged triarylamine; DOI 10.1016/j.dyepig.2023.111281

Technology Process of 1,2,3-Trifluoro-5-nitrobenzene

There total 5 articles about 1,2,3-Trifluoro-5-nitrobenzene 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: 60.0%

6-nitro-2,3,4-trifluoroaniline (148416-38-0) → 3,4,5-trifluoronitrobenzene (66684-58-0)

Guidance literature:

6-nitro-2,3,4-trifluoroaniline; With tert.-butylnitrite; In DMF (N,N-dimethyl-formamide); at 45 - 75 ℃; for 2.25 - 4h;

With hydrogenchloride; In DMF (N,N-dimethyl-formamide); water;

Reference yield:

2,3,4,5-tetrafluoro-1-nitrobenzene (5580-79-0) → 1,2,5-trifluoro-3-nitrobenzene (66684-57-9) + 3,4,5-trifluoronitrobenzene (66684-58-0)

Guidance literature:

With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; [t-BuXantphosAu]⁺[Cl-Au-Cl]^-; diphenylsilane; acetic acid; In 1,2-dichloro-ethane; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1002/adsc.201100843

Reference yield:

pentafluoronitrobenzen (880-78-4) → 1,2,5-trifluoro-3-nitrobenzene (66684-57-9) + 3,4,5-trifluoronitrobenzene (66684-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; [t-BuXantphosAu]⁺[Cl-Au-Cl]^-; diphenylsilane; acetic acid / 1,2-dichloro-ethane / 24 h / 80 °C / Inert atmosphere

2: 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; [t-BuXantphosAu]⁺[Cl-Au-Cl]^-; diphenylsilane; acetic acid / 1,2-dichloro-ethane / 24 h / 80 °C / Inert atmosphere

With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; [t-BuXantphosAu]⁺[Cl-Au-Cl]^-; diphenylsilane; acetic acid; In 1,2-dichloro-ethane;

DOI:10.1002/adsc.201100843

upstream raw materials:

3,4,5-trifluoro aniline

6-nitro-2,3,4-trifluoroaniline

pentafluoronitrobenzen

2,3,4,5-tetrafluoro-1-nitrobenzene

Downstream raw materials:

(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol

(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

[(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester

[endo-(1R,5S)-3-(2,6-difluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester

Refernces

• 1、 Zhan, Jin-Hui,Lv, Hongbin,Yu, Yi,Zhang, Jun-Long. "Catalytic C-F bond activation of perfluoroarenes by tricoordinated gold(I) complexes". . p. 1529 - 1541. Retrieved 2012/07/14.
• 2、 -. "RHO-KINASE INHIBITORS". Page/Page column 20. . Retrieved 2008/06/13.