49623-20-3

Basic information

• Product Name: 3-Isopropylbenzotrifluoride
• Synonyms: 3-Isopropylbenzotrifluoride
• CAS NO: 49623-20-3
• Molecular Formula: C₁₀H₁₁F₃
• Molecular Weight: 188.19
• Mol File: 49623-20-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Isopropylbenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isopropylbenzotrifluoride(49623-20-3)
• EPA Substance Registry System: 3-Isopropylbenzotrifluoride(49623-20-3)

Safety Data

• Hazardous Substances Data: 49623-20-3(Hazardous Substances Data)

Upstream product

• 368-79-6 2-<3-(Trifluoromethyl)phenyl>propene 
• 32454-18-5 2-m-Trifluoromethylphenyl-2-methylpropanal 
• 32445-99-1 4-isopropyl-1-(trifluoromethyl)benzene 
• 110-86-1 pyridine 
• 98-08-8 α,α,α-trifluorotoluene 
• 5161-49-9 dimethyldiazirine 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 83493-57-6 2-(m-Trifluoromethylphenyl)-2-methyl-propan-1-ol 
• 254895-41-5 methyl-2-methyl-2-(5-(trifluoromethyl)cyclohexa-2,4-dien-1-yl)propanoate 
• 1888-75-1 isopropyllithium 
• 98-82-8 Isopropylbenzene 
• 93683-27-3 perfluoro-2,4-dimethyl-3-ethylpent-3-yl radical 
• 1068-55-9 isopropylmagnesium chloride 
• 98-15-7 3-chlorotrifluoromethylbenzene 

Downstream Products

• 49623-30-5 m-Trifluormethyl-β.β-dichlor-tert.-butylbenzol 
• 98-08-8 α,α,α-trifluorotoluene 
• 32445-99-1 4-isopropyl-1-(trifluoromethyl)benzene 
• 349-76-8 3'-(trifluoromethyl)acetophenone 

Relevant articles and documents

Iron-Catalyzed Isopropylation of Electron-Deficient Aryl and Heteroaryl Chlorides

Traditional methods for the preparation of secondary alkyl-substituted aryl and heteroaryl chlorides challenge both selectivity and functional group tolerance. This contribution describes the use of statistical design of experiments to develop an effective procedure for the preparation of isopropyl-substituted (hetero)arenes with minimal isopropyl to n-propyl isomerization. The reaction tolerates electronically diverse aryl chloride coupling partners, with excellent conversion observed for strongly electron-deficient aromatic rings, such as esters and amides. Electron-rich systems, including methyl- and methoxy-substituted aryl chlorides, were found to be less reactive. Furthermore, the reaction was found to be most successful when heteroaryl chlorides were submitted to the cross-coupling protocol. By mapping substituent effects on reaction selectivity, we were able to show that electron-deficient aryl chlorides are essential for efficient coupling, and use electronic structure calculations to predict the likelihood of successful coupling through the estimation of the electron affinity of each aryl chloride. Moderate isolated yields were achieved with selected aryl chlorides, and moderate to good isolated yields were obtained for all the heteroaryl chlorides coupled. Excellent selectivity was observed when a 2,6-dichloroquinoline was used, allowing mono-substitution on a challenging substrate. (Figure presented.).

Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C-C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

ALKYLATION OF BENZOTRIFLUORIDES

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