328-75-6

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)nitrobenzene
• Synonyms: alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-5-nitro-m-xylene;Benzene, 1-nitro-3,5-bis(trifluoromethyl)-;LABOTEST-BB LT01143370;1-NITRO-3,5-BIS(TRIFLUOROMETHYL)BENZENE;1,3-BIS(TRIFLUOROMETHYL)-5-NITROBENZENE;5-NITRO-1,3-BIS(TRIFLUOROMETHYL)BENZENE;A,A,A,A',A',A'-HEXAFLUORO-5-NITRO-M-XYLENE;3,5-DI(TRIFLUOROMETHYLNITRO)BENZENE
• CAS NO: 328-75-6
• Molecular Formula: C₈H₃F₆NO₂
• Molecular Weight: 259.11
• EINECS: 206-336-6
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 328-75-6.mol

Chemical Properties

• Boiling Point: 71-72 °C(lit.)
• Flash Point: 172 °F
• Appearance: Clear yellow/Liquid
• Density: 1.535 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0416mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: 2-8°C
• BRN: 1998251
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)nitrobenzene(328-75-6)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)nitrobenzene(328-75-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25-36-37
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 328-75-6(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW LIQUID

InChI:InChI=1/C8H6F3NO3/c1-15-7-3-5(8(9,10)11)2-6(4-7)12(13)14/h2-4H,1H3

Upstream product

• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 

Downstream Products

• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 58324-87-1 3,5-bis(tri?uoromethyl)phenyl phenyl sulfide 
• 58324-86-0 2-nitro-2-(3,5-bis(trifluoromethyl)-phenyl)propane 
• 65253-34-1 2-(m,m'-Bis-trifluormethyl-phenyl)-2-nitrobutan 
• 75092-05-6 3,3′,5,5′-tetrakis(trifluoromethyl )hydrazobenzene 
• 75092-04-5 3,3′5,5′-tetrakis(trifluoromethyl)azobenzene 
• 86280-22-0 C₁₅H₈F₆NO₂ 
• 98012-88-5 6-amino-2,4-bis(trifluoromethyl)benzonitrile 
• 349-60-0 1-methoxy-3,5-bis(trifluoromethyl)benzene 
• 727741-42-6 N-(cyclohex-2-enyl)-3,5-bis(trifluoromethyl)benzenamine 
• 35564-19-3 1-fluoro-3,5-bis-(trifluoromethyl)benzene 
• 98012-95-4 N-(2-Cyano-3,5-bis-trifluoromethyl-phenyl)-acetamide 
• 16143-84-3 (3,5-bis(trifluoromethyl)methyl)acetanilide 
• 328-73-4 3,5-bis(trifluoromethyl)iodobenzene 

Relevant articles and documents

Synthesis, molecular docking studies, and larvicidal activity evaluation of new fluorinated neonicotinoids against Anopheles darlingi larvae

Anopheles darlingi is the main vector of malaria in Brazil, characterized by a high level of anthropophilia and endophagy. Imidacloprid, thiacloprid, and acetamiprid are the most widespread insecticides of the neonicotinoid group. However, they produce adverse effects on the non-target insects. Flupyradifurone has been marketed as an alternative to non-fluorinated neonicotinoids. Neonicotinoids containing trifluoroacethyl substituent reveal increased insecticidal activity due to higher hydrophobicity and metabolic stability. We synthesized novel neonicotinoid insecticides containing fluorinated acceptor groups and their interactions were estimated with the nicotinic acetylcholine receptor (nAChR) binding site by molecular docking studies, to evaluate their larvicidal activity against A. darlingi, and to assess their outdoor photodegradation behavior. New neonicotinoid analogues were prepared and characterized by NMR and mass-spectrometry. The synthesized molecules were modelled by time-dependent density functional theory and analyzed, their interaction with nAChR was investigated by molecular docking. Their insecticide activity was tested on Anopheles larvae collected in suburban area of Manaus, Brazil. Four new fluorinated neonicotinoid analogs were prepared and tested against 3rd instars larvae of A. darlingi showing high larvicidal activity. Docking studies reveal binding modes of the synthesized compounds and suggest that their insecticidal potency is governed by specific interactions with the receptor binding site and enhanced lipophilicity. 2-Chloro-5-(2-trifluoromethyl-pyrrolidin-1-ylmethyl)pyridine 5 showed fast degradation in water maintaining high larvicidal activity. All obtained substances possessed high larvicidal activity in low concentrations in 48 hours of exposure, compared to commercial flupyradifurone. Such activity is connected to a unique binding pattern of the synthesized compounds to insect's nAChR and to their enhanced bioavailability owing to introduction of fluorinated amino-moieties. Therefore, the compounds in question have a high potential for application as control agents for insects transmitting tropical diseases, and they will be less persistent in the environment.

Novel compound 1 - bromo -2 , 4, 6 -trifluoro -3, 5 -bis (trifluoromethyl) benzene and preparation method thereof (by machine translation)

The invention relates to the field of industrial organic synthesis, and particularly discloses a compound shown as a formula I, and the chemical formula is 1 - bromo -2 , 4, 6 -trifluoro -3, 5 -trifluoromethyl benzene and a preparation method thereof. The method comprises the steps of nitration, catalytic hydrogenation, chlorination, diazotization, fluoro and the like. The preparation method has the characteristics of easily available raw materials, simple process, controllable reaction conditions and the like, is suitable for industrial production and can be used as a key intermediate to prepare OLED materials. (by machine translation)

Nitration of Strongly Deactivated Aromatics with Superacidic Mixed Nitric-Triflatoboric Acid (HNO3/2CF3SO3H-B(O3SCF3)3)

The nitration of various deactivated arenes (including methanesulfonyl-, nitro-, and polyhalobenzenes) was carried out in good yield with mixed nitric-triflatoboric superacid.For example pentafluorobenzene gave pentafluoronitrobenzene in 99percent yield, nitrobenzene to m-dinitrobenzene in 92percent selectivity with 85percent overall yield, and methyl phenyl sulfone gave only the m-nitro isomer in 78percent isolated yield.Thus the new nitrating system gives high regioselectivity and yields under generally mild reaction conditions.The reagent system is compatible with many functional groups of arenes.