1481-68-1

Basic information

• Product Name: 2,4-Difluoro-5-chloronitrobenzene
• Synonyms: 5-CHLORO-2,4-DIFLUORONITROBENZENE;2,4-DIFLUORO-5-CHLORO NITROBENZENE;1-chloro-2,4-difluoro-5-nitrobenzene;5-Chloro-2,4-difluoronitrobenz;5-Chloro-2,4-difluoronitrobenze;2,4-Difluoro-5-chloronitrobenzene 1-Chloro-2,4-difluoro-5-nitrobenzene;Benzene, 1-chloro-2,4-difluoro-5-nitro-
• CAS NO: 1481-68-1
• Molecular Formula: C₆H₂ClF₂NO₂
• Molecular Weight: 193.54
• EINECS: 216-040-9
• Mol File: 1481-68-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 239.042 °C at 760 mmHg
• Flash Point: 98.369 °C
• Appearance: /
• Density: 1.591 g/cm³
• Vapor Pressure: 0.0633mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,4-Difluoro-5-chloronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Difluoro-5-chloronitrobenzene(1481-68-1)
• EPA Substance Registry System: 2,4-Difluoro-5-chloronitrobenzene(1481-68-1)

Safety Data

• Hazardous Substances Data: 1481-68-1(Hazardous Substances Data)

Usage

Description

2,4-Difluoro-5-chloronitrobenzene is an organic compound characterized by the presence of two fluorine atoms, one chlorine atom, and a nitro group attached to a benzene ring. It is a synthetic chemical used primarily in the fields of organic synthesis and pharmaceuticals.

Uses

Used in Organic Synthesis:
2,4-Difluoro-5-chloronitrobenzene is used as an intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for a range of reactions, making it a versatile building block in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-Difluoro-5-chloronitrobenzene is utilized as a key intermediate in the development of new drugs. Its specific functional groups can be modified to produce active pharmaceutical ingredients with potential therapeutic applications.
Used in Laboratory Research and Development:
2,4-Difluoro-5-chloronitrobenzene is also employed in laboratory research and development processes. It serves as a valuable compound for studying reaction mechanisms, testing new synthetic methods, and exploring the properties of novel chemical entities.
Used in Chemical Production Processes:
Finally, 2,4-Difluoro-5-chloronitrobenzene is used in chemical production processes, where it is transformed into other valuable chemicals through various chemical reactions. This contributes to the overall chemical industry by providing essential intermediates for the synthesis of a wide range of products.

Synthesis

Toluene was distilled from the mixture of potassium fluoride (38.2 g, 657 mmol), cetrimide (5.94 g, 17.6 mmol), DMF (250 mL), and dry toluene (100 mL) to remove traces of moisture. 2,4,5- Trichloronitrobenzene (7) (50.0 g, 220 mmol) was added and heated at 125 °C for 12 h under N2. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and evaporated to give a residue, which was distilled under vacuo to provide 9 (23.5 g, 55%). bp = 83 °C at 0.5 Torr, lit. bp) 85 °C at 0.5 Torr; 1H NMR (CDCl3, 200 MHz) δ 7.18 (t, 1 H, J = 9.2 Hz), 8.24 (t, 1 H, J = 7.4 Hz).

InChI:InChI=1/C6H2ClF2NO2/c7-3-1-6(10(11)12)5(9)2-4(3)8/h1-2H

Upstream product

• 89-69-0 2,4,5-Trichloronitrobenzene 
• 3115-68-2 tetrabutyl phosphonium bromide 
• 90802-25-8 2,4-Difluor-benzoldiazonium-chlorid 
• 1435-44-5 1-chloro-2,4-difluorobenzene 

Downstream Products

• 372-18-9 1,3-Difluorobenzene 
• 142335-05-5 methyl 4-chloro-5-fluoro-2-nitrophenylthioacetate 

Relevant articles and documents

Synthesis of 2,4-difluoroaniline and 1,3-difluorobenzene from 1,2,4- trichlorbenzene

Nitration of inexpensive 1,2,4-trichlorobenzene gave 2,4,5- trichloronitrobenzene (90%) which was treated with KF to form 2,4-difluoro- 5-chloronitrobenzene (70%). This was selectively hydrogenated over Pd / C to give 2,4-difluoroaniline (80%). Deamination afforded 1,3-difluorobenzene. The sequence avoids the need for costly 1,3-dichlorobenzene.

Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones

Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia, and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease, and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, and inducing anesthesia are disclosed by administering to an animal in need of such treatment an alkyl or azido-substituted 1,4-dihydroquinoxaline-2,3-dione or pharmaceutically acceptable salts thereof, which have high binding to the glycine receptor.

Process for the preparation of fluorinated benzoic acids

A process for the preparation of 2-chloro-4,5-difluorobenzoic acid and 2,4,5-trifluorobenzoic acid as well as synthetic intermediates useful in and prepared according thereto, comprising reacting a nitrobenzene having the formula STR1 wherein X is chloro or fluoro, with an appropriate carbanion to form a compound having the formula STR2 wherein one of Y and Z is chloro and the other is nitro, and R is a radical selected from the group consisting of --CCl3, --CH2 NO2, --CH(NO2)R1, --CH(CO2 R1)2, --CH(C(O)R2)2, --CH(CN)CO2 R1, --CH(CO2 R1)COR2 and --COR2 where R1 is alkyl or arylalkyl and R2 is alkyl, aryl or arylalkyl and, where appearing more than once in such a radical, R1 and R2 may be the same or different at each occurrence.