10557-13-8

Basic information

• Product Name: 1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione
• Synonyms: 1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione97%;4-(2-Oxopropanoyl)benzotrifluoride, 2-Oxo-4'-(trifluoromethyl)propiophenone;1,2-Propanedione,1-[4-(trifluoromethyl)phenyl]-
• CAS NO: 10557-13-8
• Molecular Formula: C₁₀H₇F₃O₂
• Molecular Weight: 216.16
• Mol File: 10557-13-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 30-32
• Boiling Point: 250.1°C at 760 mmHg
• Flash Point: 95.2°C
• Appearance: /
• Density: 1.285g/cm³
• Vapor Pressure: 0.022mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: 1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione(10557-13-8)
• EPA Substance Registry System: 1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione(10557-13-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 10557-13-8(Hazardous Substances Data)

Usage

General Description

1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione, also known as 4'-trifluoromethylacetophenone, is an organic compound with the chemical formula C11H9F3O. It is a flavor and fragrance ingredient that is commonly used in the production of food flavors and perfumes. This chemical is a pale yellow, crystalline solid with a sweet, floral odor. It is synthesized through the Friedel-Crafts acylation of benzene with trifluoroacetyl chloride, followed by reduction of the resulting ketone. 1-[4-(Trifluoromethyl)phenyl]propane-1,2-dione is also utilized in the pharmaceutical industry and has applications in the synthesis of various pharmaceutical drugs. However, it is important to handle this compound with care, as it is considered potentially hazardous and should be used in a well-ventilated area with appropriate protective equipment.

InChI:InChI=1/C10H7F3O2/c1-6(14)9(15)7-2-4-8(5-3-7)10(11,12)13/h2-5H,1H3

Upstream product

• 75-52-5 nitromethane 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 79756-87-9 1-(prop-1-ynyl)-4-trifluoromethylbenzene 

Downstream Products

• 1421922-50-0 2,5-dimethyl-4-{[4-(propan-2-yloxy)-1,3-thiazol-2-yl]methyl}aniline 

Relevant articles and documents

Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts

Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.

Reactions and reactivity of acyloxycarbenes

Phenylacetoxycarbene, phenyl(pivaloyloxy)carbene, and phenyl(benzoyloxy)carbene, photolytically generated from diazirine precursors in pentane at 25°C, efficiently rearranged by 1,2-acyl migrations to give high yields of the appropriate 1,2-diketones. The kinetics of these rearrangements were determined by laser flash photolysis. Substituent effects on the acyl migrations and ab initio electronic structure calculations on ground state carbenes and transition states were employed to analyze the rearrangement mechanism. Additions of phenylacetoxycarbene to alkenes proceeded in good yields, in lieu of the 1,2-acyl shift; absolute rate constants were obtained for these reactions of the ambiphilic carbene. (Phenoxymethyl)acetoxycarbene gave only a 1,2-H shift; the potentially competitive 1,2-acetyl migration was suppressed.