30071-93-3

Basic information

• Product Name: 3',5'-Bis(trifluoromethyl)acetophenone
• Synonyms: 3',5'-Bis(trifluoromethyl)acetophenone 98%;3,5-BIS(TRIFLUOROMETHYL);TRIFLUOROMETHYL ACETOPHENONE;3,5-Di(trifluoromethyl)hypnone;3',5'-Bis(trifluorom;3,5-(CF3)2-acetophenone;3, 5 - two-trifluoroMethyl;1-[3,5-Bis(trifluoromethyl)phenyl]ethan-1-one, 5-Acetyl-alpha,alpha,alpha,alpha',alpha',alpha'-hexafluoro-m-xylene
• CAS NO: 30071-93-3
• Molecular Formula: C₁₀H₆F₆O
• Molecular Weight: 256.14
• EINECS: 250-023-7
• Product Categories: Fluorides;Trifluoromethylbenzene serise;Boronic Acid series;PHARMACEUTICAL INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);ketone;Miscellaneous;C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Indolines ,Indoles
• Mol File: 30071-93-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 95-98 °C (15 mmHg)
• Flash Point: 180 °F
• Appearance: clear pale yellow liquid
• Density: 1.422 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.836mmHg at 25°C
• Refractive Index: n20/D 1.4221(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2384789
• CAS DataBase Reference: 3',5'-Bis(trifluoromethyl)acetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-Bis(trifluoromethyl)acetophenone(30071-93-3)
• EPA Substance Registry System: 3',5'-Bis(trifluoromethyl)acetophenone(30071-93-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-36
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 30071-93-3(Hazardous Substances Data)

Usage

Description

3',5'-Bis(trifluoromethyl)acetophenone is an organic compound characterized by its clear pale yellow liquid appearance. It is known for its chemical structure that includes two trifluoromethyl groups attached to a benzene ring, with a carbonyl group attached to the side chain.

Uses

Used in Pharmaceutical Industry:
3',5'-Bis(trifluoromethyl)acetophenone is used as a reactant for the preparation of pyrazole carboxamide derivatives, which possess significant antibacterial and antifungal properties. These derivatives are valuable in the development of new drugs to combat various bacterial and fungal infections, making this compound an important contributor to the pharmaceutical industry.
Used in Chemical Synthesis:
As a versatile reactant, 3',5'-Bis(trifluoromethyl)acetophenone can be utilized in various chemical synthesis processes, particularly in the creation of complex organic molecules with potential applications in different fields, such as materials science, agrochemicals, and more. Its unique structure and reactivity make it a valuable building block for the synthesis of a wide range of compounds.

InChI:InChI=1/C7H11F3O/c8-7(9,10)5-1-3-6(11)4-2-5/h5-6,11H,1-4H2

Upstream product

• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 108-24-7 acetic anhydride 
• 401-96-7 3,5-bis(trifluoromethyl)benzoyl fluoride 
• 594-27-4 tetramethylstannane 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 349-59-7 3,5-bis(trifluoromethyl)styrene 
• 75-36-5 acetyl chloride 
• 5780-37-0 (E)-acetaldoxime 
• 725-89-3 3,5-bistrifluoromethylbenzoic acid 
• 917-54-4 methyllithium 
• 68120-60-5 1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol 
• 112981-69-8 3,5-bis(trifluoromethyl)phenylmagnesium bromide 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 785-56-8 3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride 

Downstream Products

• 68120-60-5 1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-ol 
• 742097-67-2 N-(1-(3,5-bis(trifluoromethyl)phenyl)ethyl)formamide 
• 530441-95-3 (R)-1-(1-(bromomethoxy)ethyl)-3,5-bis(trifluoromethyl)benzene 
• 345580-18-9 (S)-2-amino-3-[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-N-methyl-2-phenylpropionamide 
• 345578-66-7 (R)-4-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxymethyl]-4-phenyl-imidazolidin-2-one 
• 345579-91-1 (S)-5-[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxymethyl]-5-phenylimidazolidine-2,4-dione 
• 618096-34-7 (S)-5-[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxymethyl]-(R)-2-tert-butyl-3-methyl-5-phenylimidazolidin-4-one 
• 511256-36-3 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-N-methylethanamine 
• 511256-31-8 [(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethyl]-methyl-((S)-1-phenyl-ethyl)-amine 
• 384824-41-3 [(S)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-amine 
• 511256-29-4 [(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-amine 
• 392655-32-2 C₁₈H₁₅F₆N 
• 1227953-47-0 ethyl 6-(3,5-bis(trifluoromethyl)phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylate 
• 1294503-01-7 9-(4-chlorophenyl)-2-(3,5-di(trifluoromethyl)phenyl)-7-phenyl-7H-pyrazolo[3,4-h][1,6]naphthyridine 

Relevant articles and documents

An improved preparation of 3,5-bis(trifluoromethyl)acetophenone and safety considerations in the preparation of 3,5-bis(trifluoromethyl)phenyl Grignard reagent

An improved and efficient bromination of 3,5-bis(trifluoromethyl)benzene was developed. A safe and reliable preparation of the potentially explosive 3,5-bis(trifluoromethyl)phenyl Grignard and 3-trifluoromethylphenyl Grignard reagents, from the precursor bromides, is described. Reaction System Screening Tool (RSST) and Differential Thermal Analysis (DTA) studies suggest these trifluoromethylphenyl Grignard reagents can detonate on loss of solvent contact or upon moderate heating. When prepared and handled according to the methods described herein, these Grignard reagents can be safely prepared and carried on to advanced intermediates.

Preparation method of 3, 5-bis (trifluoromethyl) acetophenone

The invention provides a preparation method of 3, 5-bis (trifluoromethyl) acetophenone. 3, 5-bis (trifluoromethyl) acetophenone is synthesized by using 3, 5-bis (trifluoromethyl) bromobenzene as a rawmaterial. The preparation method comprises the following steps: under a reaction temperature, selectively mixing either N-methoxy-N-methylacetamide or N-methoxy-N-methylformamide with 3, 5-bis (trifluoromethyl) bromobenzene and n-butyl lithium, and carrying out a stirring reaction under a reaction solvent condition at a reaction temperature of -70 to -90 DEG C; and executing a post-processing step, namely, heating to room temperature, extraction and washing, drying and evaporating to remove the residual solvent, and performing column chromatography separation to obtain 3, 5-bis (trifluoromethyl) acetophenone. According to the invention, cheap 3, 5-bis (trifluoromethyl) bromobenzene as a raw material directly reacts with N-methoxy-N-methylacetamide to obtain the high-yield 3, 5-bis (trifluoromethyl) acetophenone, the method is simple in reaction steps, easy to control and suitable for industrial production, so that a more valuable synthesis route is provided for preparation of aprepitant, good social benefits and economic benefits can be brought, and the economic value potential is relatively large.

A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction

An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).