78950-29-5

Basic information

• Product Name: 4-(Trifluoromethyl)phenyl acetate
• Synonyms: 4-(TRIFLUOROMETHYL)PHENYL ACETATE;TrifluoroMethyl Methyl;4-(Acetoxy)benzotrifluoride, Acetic acid 4-(trifluoromethyl)phenyl ester
• CAS NO: 78950-29-5
• Molecular Formula: C₉H₇F₃O₂
• Molecular Weight: 204.15
• Mol File: 78950-29-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 207.2 °C at 760 mmHg
• Flash Point: 68.8 °C
• Appearance: /
• Density: 1.271 g/cm³
• Vapor Pressure: 0.228mmHg at 25°C
• Refractive Index: 1.443
• CAS DataBase Reference: 4-(Trifluoromethyl)phenyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethyl)phenyl acetate(78950-29-5)
• EPA Substance Registry System: 4-(Trifluoromethyl)phenyl acetate(78950-29-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 78950-29-5(Hazardous Substances Data)

Usage

General Description

4-(Trifluoromethyl)phenyl acetate, also known as para-Trifluoromethylphenyl acetate or p-TFMPA is an organic compound with the molecular formula C9H7F3O2. This chemical is characterized by the presence of a trifluoromethyl group (-CF3) and an acetate group (-COOCH3) attached to a phenyl ring. It is commonly used as a reagent in organic synthesis, particularly in the formation of arylic and aliphatic compounds. The trifluoromethyl group is electron withdrawing, which makes this compound useful in processes that require a high degree of stability and resistance against reactions. It's also used in the pharmaceutical and agrochemical industries. The chemical is typically a clear colorless liquid and should be handled with care as it may cause irritation to the skin and eyes.

InChI:InChI=1/C9H7F3O2/c1-6(13)14-8-4-2-7(3-5-8)9(10,11)12/h2-5H,1H3

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 402-45-9 4-hydroxybenzotrifluoride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 108-24-7 acetic anhydride 
• 33035-41-5 2-(diacetoxyiodo)mesitylene 
• 75-36-5 acetyl chloride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 127-09-3 sodium acetate 
• 455-13-0 4-Iodobenzotrifluoride 
• 6018-89-9 nickel(II) acetate tetrahydrate 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 64-19-7 acetic acid 
• 33527-94-5 4-acetoxyiodobenzene 

Downstream Products

• 721-63-1 (4-trifluoromethylphenyl)acetic acid ethyl ester 

Relevant articles and documents

Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling

The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to al

Donor-Acceptor Fluorophores for Energy-Transfer-Mediated Photocatalysis

Triplet-triplet energy transfer (EnT) is a fundamental activation pathway in photocatalysis. In this work, we report the mechanistic origins of the triplet excited state of carbazole-cyanobenzene donor-acceptor (D-A) fluorophores in EnT-based photocatalytic reactions and demonstrate the key factors that control the accessibility of the 3LE (locally excited triplet state) and 3CT (charge-transfer triplet state) via a combined photochemical and transient absorption spectroscopic study. We found that the energy order between 1CT (charge transfer singlet state) and 3LE dictates the accessibility of 3LE/3CT for EnT, which can be effectively engineered by varying solvent polarity and D-A character to depopulate 3LE and facilitate EnT from the chemically more tunable 3CT state for photosensitization. Following the above design principle, a new D-A fluorophore with strong D-A character and weak redox potential is identified, which exhibits high efficiency for Ni(II)-catalyzed cross-coupling of carboxylic acids and aryl halides with a wide substrate scope and high selectivity. Our results not only provide key fundamental insight on the EnT mechanism of D-A fluorophores but also establish its wide utility in EnT-mediated photocatalytic reactions.

TCDA: Practical Synthesis and Application in the Trifluoromethylation of Arenes and Heteroarenes

A practical synthesis of the reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported on 50 g scale. The trifluoromethylation with TCDA was optimized, and the reaction shows very broad scope with respect to electron-deficient, -neutral, -rich aryl/heteroaryl iodides, as well as excellent functional group tolerability, such as ester, amide, aldehyde, hydroxyl, and carboxylic acid. The reagent was also applied to the late-stage trifluoromethylation of three medicinally relevant compounds. Additionally, the building block trifluoromethylpyridine and one drug related molecule Boc-Fluoxetin were synthesized in 10 g scale by this method, demonstrating its practical applications in process chemistry.