402-54-0

Basic information

• Product Name: 4-Nitrobenzotrifluoride
• Synonyms: 1-Nitro-4-(trifluoromethyl)benzene;1-Nitro-4-trifluoromethyl-benzene;4-(Trifluoromethyl)nitrobenzene;Benzene, 1-nitro-4-(trifluoromethyl)-;p-nitrotrifluorotoluene;nitrobenzotrifluorides;p-Nitro(trifluoromethyl)benzene;p-Nitrobenzotrifluoride
• CAS NO: 402-54-0
• Molecular Formula: C₇H₄F₃NO₂
• Molecular Weight: 191.11
• EINECS: 206-948-3
• Product Categories: Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 402-54-0.mol
• Article Data: 96

Chemical Properties

• Melting Point: 38-40 °C(lit.)
• Boiling Point: 81-83 °C10 mm Hg(lit.)
• Flash Point: 191 °F
• Appearance: White to yellow/Crystalline Powder, Crystals or Crystalline Mass
• Density: 1.3910 (estimate)
• Vapor Pressure: 0.454mmHg at 25°C
• Refractive Index: 1.524
• Solubility: soluble in Methanol
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents, strong reducing agents.
• CAS DataBase Reference: 4-Nitrobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrobenzotrifluoride(402-54-0)
• EPA Substance Registry System: 4-Nitrobenzotrifluoride(402-54-0)

Safety Data

• Hazard Codes: T+,T,Xi
• Statements: 22-26-36/37/38-21/22
• Safety Statements: 26-28-36/37-45-36/37/39-28A
• RIDADR: UN 3431 6.1/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 402-54-0(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liqui

Synthesis Reference(s)

Synthesis, p. 932, 1980 DOI: 10.1055/s-1980-29276Tetrahedron Letters, 32, p. 91, 1991 DOI: 10.1016/S0040-4039(00)71226-3

General Description

A thin, oily straw colored liquid with a fishlike odor. May be toxic by ingestion, inhalation and skin absorption. Insoluble in water and denser than water. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

InChI:InChI=1/C7H5Cl2F/c8-7(9)5-2-1-3-6(10)4-5/h1-4,7H

Upstream product

• 14505-17-0 p-nitrobenzylidyne tribromide 
• 402-14-2 2-nitro-5-(trifluoromethyl)aniline 
• 62-23-7 4-nitro-benzoic acid 
• 636-98-6 p-nitrobenzene iodide 
• 2314-97-8 iodotrifluoromethane 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 371-76-6 bis(trifluoromethyl)mercury 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 455-14-1 4-trifluoromethylphenylamine 
• 74087-85-7 3,3-dimethyldioxirane 
• 98-08-8 α,α,α-trifluorotoluene 
• 619-50-1 4-nitrobenzoic acid methyl ester 

Downstream Products

• 455-14-1 4-trifluoromethylphenylamine 
• 1030-22-4 1,2-bis(4-cyanophenyl)diazene oxide 
• 75-07-0 acetaldehyde 
• 35848-46-5 4-(α,α,α-Trifluoromethyl)nitrobenzene radical anion 
• 122947-73-3 2-Dichloromethyl-1-nitro-4-trifluoromethyl-benzene 
• 122947-74-4 2-Dibromomethyl-1-nitro-4-trifluoromethyl-benzene 
• 67-64-1 acetone 
• 89303-21-9 2-Benzenesulfonylmethyl-1-nitro-4-trifluoromethyl-benzene 
• 117508-93-7 1-(5-trifluoromethyl-2-nitrophenyl)ethyl phenyl sulphone 
• 2367-02-4 1-phenoxy-4-(trifluoromethyl)benzene 
• 402-17-5 2-nitro-5-trifluoromethylphenol 
• 102512-07-2 N-(4-(trifluoromethyl)phenyl)hydroxylamine 
• 3284-64-8 1-nitro-4-(trichloromethyl)benzene 
• 34913-29-6 4,4′-bis(trifluoromethyl)azobenzene 

Relevant articles and documents

Aromatic trifluoromethylation catalytic in copper

Cu(i)-diamine complexes were found to catalyse the trifluoromethylation of aryl iodides. In the presence of a small amount of CuX (X = Cl, Br, I) and 1,10-phenanthroline (phen), the cross-coupling reactions of iodoarenes with trifluoromethylsilanes proceeded smoothly to afford trifluoromethylated aromatics in good yields.

Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qualitative and quantitative studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligandless [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

NOVEL METHOD FOR PRODUCING PERFLUOROALKYLATING AGENTS USING MONOHYDROPERFLUOROALKANE AS STARTING MATERIAL, AND METHOD FOR PRODUCING AROMATIC PERFLUOROALKYL COMPOUNDS USING THE SAME

To provide a simple method for producing silylated trifluoromethylcarbinol from trifluoromethane.SOLUTION: There is provided a method for producing a compound represented by the formula [1], in which the compound is obtained by reacting a monohydroperfluoroalkane, a carbonyl compound, and NaH in an organic solvent and then reacting the reaction solution with a silylating agent. [In the formula, RF is an alkyl group such as a linear chain of C1 to 2, and a perfluoroalkyl group in which all H on C is substituted with F; R1 and R2 are independently alkyl groups such as a linear chain of H or C1 to 2, or the like respectively; R1 and R2 may be integrated to form a ring; and R3, R4 and R5 are independently H or C1 to 2 linear alkyl groups, or the like respectively.]SELECTED DRAWING: None