713-65-5

Basic information

• Product Name: 4-(Trifluoromethoxy)nitrobenzene
• Synonyms: TIMTEC-BB SBB001666;P-NITRO (TRIFLUOROMETHOXY) BENZENE;4-(TRIFLUOROMETHOXY)NITROBENZENE;4-NITRO-1-TRIFLUOROMETHOXYBENZENE;1-NITRO-4-(TRIFLUOROMETHOXY)BENZENE;4-nitrotrifluoromethoxybenzene;p-Nitro (Trifluoromethoxy) Benzene 4-(Trifluoromethoxy)nitrobenzene;4-(trifluoromrthoxy)nitrobebzene
• CAS NO: 713-65-5
• Molecular Formula: C₇H₄F₃NO₃
• Molecular Weight: 207.11
• EINECS: -0
• Mol File: 713-65-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 15°C
• Boiling Point: 87 °C
• Flash Point: 87-89°C/15mm
• Appearance: /
• Density: 1,447 g/cm3
• Vapor Pressure: 0.196mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 1966388
• CAS DataBase Reference: 4-(Trifluoromethoxy)nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethoxy)nitrobenzene(713-65-5)
• EPA Substance Registry System: 4-(Trifluoromethoxy)nitrobenzene(713-65-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 713-65-5(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow liquid

Uses

1-Nitro-4-(trifluoromethoxy)benzene can be used to manufacture tobacco flavor.

InChI:InChI=1/C7H4F3NO3/c8-7(9,10)14-6-3-1-5(2-4-6)11(12)13/h1-4H

Upstream product

• 456-55-3 1-trifluoromethoxybenzene 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 100-01-6 4-nitro-aniline 
• 57830-55-4 2-((trifluoromethyl)sulfonyl)pyridine 
• 98-95-3 nitrobenzene 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 139301-27-2 4-trifluoromethoxyphenylboronic acid 
• 34888-05-6 (trichloromethoxy)benzene 
• 100-66-3 methoxybenzene 
• 1394827-04-3 potassium (4-(trifluoromethoxy)phenyl)trifluoroborate 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 22172-64-1 3-Phenyl-5-trifluormethoxy-anthranil 
• 461-82-5 4-(trifluoromethoxy)aniline 

Relevant articles and documents

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Trifluoromethoxylated aromatics (ArOCF3) are valuable structural motifs in the area of drug discovery due to the enhancement of their desired physicochemical properties upon the introduction of the trifluoromethoxy group (CF3O). Although significant progress has been made recently in the introduction of CF3O group into aromatics, current methods either require the use of expensive trifluoromethoxylation reagents or require harsh reaction conditions. We present a conceptually new and operationally simple protocol for the direct C?H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochemical reaction conditions. This reaction proceeds through the initial generation of CF3 radical followed by conversion to CF3O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochemical trifluoromethoxylation is illustrated by the direct incorporation of CF3O group into a variety of (hetero)aromatics as well as bio-relevant molecules.

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison t