104201-66-3

Basic information

• Product Name: (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester
• Synonyms: (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester;(E)-3-(Trifluoromethyl)cinnamic acid methyl ester;(E)-Methyl 3-(3-(Trifluoromethyl)Phenyl)Acrylate;(E)-Methyl 3-(3-(Trifluoromethyl)Phenyl)Acrylate(WXC02699)
• CAS NO: 104201-66-3
• Molecular Formula: C₁₁H₉F₃O₂
• Molecular Weight: 230.1831696
• Mol File: 104201-66-3.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester(104201-66-3)
• EPA Substance Registry System: (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester(104201-66-3)

Safety Data

• Hazardous Substances Data: 104201-66-3(Hazardous Substances Data)

Usage

Description

(2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester, also known as (2E)-methyl 3-(3-(trifluoromethyl)phenyl)prop-2-enoate, is an organic compound characterized by its molecular formula C11H9F3O2. This colorless to light yellow liquid with a fruity odor is insoluble in water but readily soluble in organic solvents. It is a methyl ester derivative of (2E)-3-[3-(trifluoromethyl)phenyl]-2-propenoic acid, and its trifluoromethyl group endows it with unique properties that are valuable in pharmaceutical research and drug discovery.

Uses

Used in Pharmaceutical Industry:
(2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester is used as an intermediate in the synthesis of various pharmaceuticals. Its trifluoromethyl group contributes to the development of new drugs with improved pharmacological properties.
Used in Agricultural Industry:
In the agricultural sector, (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester serves as an intermediate in the production of agrochemicals, potentially enhancing the effectiveness of crop protection agents.
Used in Flavors and Fragrances Production:
This chemical also has potential applications in the creation of flavors and fragrances, where its fruity odor can be utilized to develop new scents and tastes for various consumer products.
Safety Precautions:
It is crucial to handle (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester with care, as it may pose risks if ingested, inhaled, or comes into contact with skin and eyes. Proper safety measures should be taken to minimize exposure and ensure the well-being of individuals working with this compound.

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 292638-85-8 acrylic acid methyl ester 
• 16695-14-0 Malonic acid monomethyl ester 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 98-16-8 3-trifluoromethylaniline 
• 67-56-1 methanol 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 351-36-0 N-acetyl-3-trifluoromethylbenzenamine 
• 1384879-94-0 (E)-methyl 3-oxo-3-[2-(3-trifluoromethylstyryl)phenyl]propanoate 
• 454-87-5 3-(trifluoromethyl)benzenediazonium tetrafluoroborate 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 113048-69-4 (E)-3-(3-trifluoromethylphenyl)prop-2-en-1-ol 
• 294856-02-3 methyl 3-(3-(trifluoromethyl)phenyl)propanoate 
• 104201-78-7 4-Oxo-2-(3-trifluoromethyl-phenyl)-cyclopentane-1,1-dicarboxylic acid 
• 351536-26-0 tert-butyl-dimethyl-[1-trichloromethyl-3-(3-trifluoromethyl-phenyl)-allyloxy]-silane 

Relevant articles and documents

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer

Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).

Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines

N-(Aryloxy)imines, readily accessible by condensation/tautomerization of (pseudo)benzylic primary amines and 2,6-di-tert-butyl-1,4-benzoquinone, undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative C-C bond-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonates. This reactivity umpolung enables the formal α-allylation of (pseudo)benzylic primary amines. Mechanistic studies reveal that the apparent regioselectivity of the desired bond-forming event is a convergent process that is initiated by unselective allylation of N-(aryloxy)imines to give several regioisomeric species, which subsequently rearrange via stepwise [1,3]- or concerted [3,3]-sigmatropic shifts, ultimately converging to provide the desired regioisomer of the amine products.