16185-96-9

Basic information

• Product Name: 2'-(Trifluoromethyl)propiophenone
• Synonyms: 2'-(TRIFLUOROMETHYL)PROPIOPHENONE;2-(TRIFLUOROMETHYL)PROPIOPHENONE;1-[2-(Trifluoromethyl)phenyl]-1-propanone;o-Trifluoromethylpropiophenone;2'-(Trifluoromethyl)propiophenone 97%;2'-(Trifluoromethyl)propiophenone97%;1-(2-(trifluoromethoxy)phenyl)propan-1-one;1-(2-(trifluoromethyl)phenyl)propan-1-one
• CAS NO: 16185-96-9
• Molecular Formula: C₁₀H₉F₃O
• Molecular Weight: 202.17
• Product Categories: C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Fluorine series
• Mol File: 16185-96-9.mol

Chemical Properties

• Boiling Point: 219-220 °C(lit.)
• Flash Point: 214 °F
• Appearance: /
• Density: 1.214 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.461(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2263292
• CAS DataBase Reference: 2'-(Trifluoromethyl)propiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-(Trifluoromethyl)propiophenone(16185-96-9)
• EPA Substance Registry System: 2'-(Trifluoromethyl)propiophenone(16185-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16185-96-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-(Trifluoromethyl)propiophenone is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and enhancing the therapeutic potential of existing medications.
Used in Agrochemical Industry:
In the agrochemical sector, 2'-(Trifluoromethyl)propiophenone is utilized as a key intermediate in the production of agrochemicals, aiding in the development of effective pest control agents and crop protection products.
Used in Organic Synthesis:
2'-(Trifluoromethyl)propiophenone is employed as a reagent in the synthesis of a wide range of organic compounds, facilitating the creation of novel chemical entities and expanding the scope of chemical research.
Used in Analytical Chemistry and Biochemical Research:
Leveraging its strong oxidizing properties, 2'-(Trifluoromethyl)propiophenone is used in analytical chemistry and biochemical research for various applications, including the analysis of complex chemical structures and the study of biological processes.
It is essential to handle and store 2'-(Trifluoromethyl)propiophenone with caution due to its flammability and potential health hazards, ensuring safety in its applications across different industries.

InChI:InChI=1/C10H9F3O/c1-2-9(14)7-5-3-4-6-8(7)10(11,12)13/h3-6H,2H2,1H3

Upstream product

• 197508-95-5 1-(2-trifluoromethylphenyl)-1-propanol 
• 447-61-0 2-Trifluoromethylbenzaldehyde 
• 123-62-6 propionic acid anhydride 
• 3796-19-8 2-trifluoromethylphenylmagnesium chloride 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 

Downstream Products

• 104384-69-2 2-bromo-1-[2-(trifluoromethyl)phenyl]propan-1-one 
• 1415763-97-1 1-(2-(trifluoromethyl)phenyl)-1-oxopropan-2-yl 4-methylbenzenesulfonate 
• 1072195-82-4 (S)-1-(2-hydroxyethyl)-4-methyl-N-[4-(methylsulfonyl)phenyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxamide 

Relevant articles and documents

Preparation of Trifluoromethylphenyl Magnesium Halides in the Presence of LiCl and Synthesis of 2′-Trifluoromethyl-Aromatic Ketones

The effect of LiCl-promoted insertion of magnesium turnings into halogenated-trifluoromethylbenzenes for Grignard reagent synthesis was investigated. In the presence of less than 1.0 equiv of LiCl, chloro(trifluoromethyl)benzene Grignard reagents were easily generated. The 2-trifluoromethylphenyl magnesium chloride Grignard reagent was obtained in high yield and 2′-trifluoromethyl-substituted aromatic ketone was synthesized through reaction of the obtained Grignard reagent with a carboxylic anhydride in an 83% yield.

METHOD OF PRODUCING HIGH-PURITY TRIFLUOROMETHYL GROUP-SUBSTITUTED AROMATIC KETONE

PROBLEM TO BE SOLVED: To provide a method of producing high-purity trifluoromethyl group-substituted aromatic ketone with a high yield. SOLUTION: The trifluoromethyl group-substituted aromatic ketone is improved in a distillation yield to attain high purity by the steps of: reacting a halogen-substituted benzotrifluoride compound with a magnesium metal to convert to a Grignard reagent; reacting the Grignard reagent with an acid anhydride; thereafter subjecting to hydrolysis treatment with an aqueous solution containing an acid to produce trifluoromethyl-substituted aromatic ketone; and thereafter subjecting to hydrolysis treatment under a basic condition using an aqueous solution containing a base to decompose and remove aliphatic fatty acid halogenated butyl ester, and aliphatic fatty acid trifluoromethyl phenyl ester which are hard to be distilled and removed from trifluoromethyl group-substituted aromatic ketone. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT

METHOD OF PRODUCING 2'-TRIFLUOROMETHYL GROUP-SUBSTITUTED AROMATIC KETONE

A method produces a 2′-trifluoromethyl-substituted aromatic ketone and includes reacting a 2-halogen-substituted benzotrifluoride compound with magnesium metal to convert the compound to a Grignard reagent; and reacting the Grignard reagent with an acid anhydride; and then hydrolyzing the resultant to produce a 2′-trifluoromethyl-substituted aromatic ketone. The method of producing a 2′-trifluoromethyl-substituted aromatic ketone enables 2′-trifluoromethyl-substituted aromatic ketone to be produced without using expensive raw materials by generating a Grignard reagent as an intermediate and reacting this Grignard reagent with an acid anhydride in an efficient productivity. The 2′-trifluoromethyl-substituted aromatic ketone that is produced by the method of producing a 2′-trifluoromethyl-substituted aromatic ketone can be used as fine chemicals, raw materials for pharmaceuticals and agrochemicals, raw materials for resins and plastics, electronics and information related materials, optical materials, and the like.

Diminished reactivity of ortho-substituted phenacyl bromides toward nucleophilic displacement

A systematic increase of substitution rates by tert-butylamine on α-bromopropiophenones is observed with meta or para substituents with increasing electron-withdrawing ability (k x 103 L M-1 min-1 = 12.7 (p-CH3), 15.7 (o-F), 20.5 (H), 20.0 (p-Cl), 23.6 (m-Cl), 27.3 (p-CF3)). Within an ortho-substituted series, the reactivities decrease (k x 103 L M-1 min-1 = 7.64 (o-OCH3), 5.31 (o-CH3), 2.85 (o-Cl), 2.40 (o-CF3)). Ortho-substitution results occur from rotational barrier effects and an Aδσ + Bδσ + repulsion. The major bonding contribution between reaction and α-substituent centers (A-B) is only the σ bond. When π bonding is allowed between A and B (meta/para-substitution), delocalization and stabilization of the reacting center occurs.

Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants

Some novel 2-methyl-3-aminopropiophenones were synthesized and their centrally acting muscle relaxant activities were,evaluated for an inhibitory effect on the flexor reflex in rats. The structure-activity relationships are discussed. In this series 2-methyl-3-pyrrolidino-1-(4-trifluoromethylphenyl)-propan-1-one (28) showed significant centrally acting muscle relaxant activity. In addition, the activities of each enantiomer (28-(S) and (R)) were studied along with their acute toxicities. Compound 28-(R) was found to exhibit more potent activity and weaker acute toxicity than 28-(S). Accordingly, compound 28-(R) (NK433) is under development as a novel centrally acting muscle relaxant.