421-50-1

Basic information

• Product Name: 1,1,1-Trifluoroacetone
• Synonyms: TRIFLUOROACETONE;1,1,1-trifluoro-2-propanon;3,3,3-Trifluoroacetone;CH3COCF3;Methyl trifluoromethyl ketone;Trifluoromethyl methyl ketone;1,1,1-TRIFLUOROACETONE;1,1,1-TRIFLUORO-2-PROPANONE
• CAS NO: 421-50-1
• Molecular Formula: C₃H₃F₃O
• Molecular Weight: 112.05
• EINECS: 207-005-9
• Product Categories: C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 421-50-1.mol
• Article Data: 41

Chemical Properties

• Melting Point: -78 °C
• Boiling Point: 22 °C(lit.)
• Flash Point: −23 °F
• Appearance: Clear colorless/Liquid
• Density: 1.252 g/mL at 25 °C(lit.)
• Vapor Pressure: 13.62 psi ( 20 °C)
• Refractive Index: n20/D 1.3(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• Water Solubility: Miscible
• Sensitive: Lachrymatory
• Stability: Volatile
• BRN: 1748614
• CAS DataBase Reference: 1,1,1-Trifluoroacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-Trifluoroacetone(421-50-1)
• EPA Substance Registry System: 1,1,1-Trifluoroacetone(421-50-1)

Safety Data

• Hazard Codes: F+,Xi,F
• Statements: 12-36/37/38
• Safety Statements: 16-26-29-33-36-7/9-9-37/39-39
• RIDADR: UN 1993 3/PG 1
• WGK Germany: 3
• F: 19
• TSCA: T
• HazardClass: 3
• PackingGroup: I
• Hazardous Substances Data: 421-50-1(Hazardous Substances Data)

Usage

Chemical Properties

1,1,1-Trifluoroacetone is CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 421-50-1 differently. You can refer to the following data:
1. 1,1,1-Trifluoroacetone is used as intermediate of bioactive substance and antihypertensive drug, and as effective synthetic building block and trifluoromethyl reaction reagent.
2. 1,1,1-Trifluoroacetone is a general chemical reagent used in the synthesis of glucokinase-glucokinase regulatory protein) GK-GKRP disruptors which may act as potential targets for type II diabetics. Reactant for enantioselective cycloadditions.
3. Used in a synthesis of 2-trifluoromethyl-7-azaindoles starting with 2,6-dihalopyridines. The derived chiral imine was used to prepare enantiopure α-trifluoromethyl alanines and diamines via a Strecker reaction followed by either nitrile hydrolysis or reduction.

InChI:InChI=1/C3H3F3O/c1-2(7)3(4,5)6/h1H3

Upstream product

• 2253-00-1 1,1,3,3,3-pentafluoro-2-methyl-1-propene 
• 334-98-5 (trifluoro methyl) magnesiumiodide 
• 75-36-5 acetyl chloride 
• 2229-07-4 methyl radical 
• 684-16-2 Hexafluoroacetone 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 75-05-8 acetonitrile 
• 359-41-1 1,1,1-trifluoro-2,3-epoxypropane 
• 163133-86-6 pyrimidin-4-amine 
• 64723-97-3 1,1,1-trifluoroacetone enolate anion 
• 120-72-9 indole 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 66929-54-2 (Z)-1,1,1-trifluoro-4-hydroxy-4-phenylbut-3-en-2-one 
• 7291-30-7 Z-1,1,1-trifluoro-4-hydroxypent-3-ene-2-one 

Downstream Products

• 428-70-6 1,1,1-trifluoro-2-methyl-3-nitropropan-2-ol 
• 379-19-1 2,2-bis-(4-chloro-phenyl)-1,1,1-trifluoro-propane 
• 65138-47-8 5,5,7-Trimethyl-2,2-diphenyl-7-(trifluormethyl)-6-oxa-1-aza-5λ⁵-phosphabicyclo<3.2.0>hept-3-en-3,4-dicarbonsaeure-dimethylester 
• 1588-37-0 N-[2,2,2-trifluoro-1-methylethylidene]aniline 
• 64750-89-6 4,4,4-Trifluor-3-methyl-2-butensaeure-ethylester 
• 27970-78-1 Phenyl-methanesulfonic acid 1-trifluoromethyl-vinyl ester 
• 507-52-8 2-(trifluoromethyl)-2-propanol 
• 426-54-0 1,1,1-trifluoro-2-phenylpropan-2-ol 
• 76953-96-3 1-(4-methoxyphenyl)-1-(trifluoromethyl)ethanol 
• 131131-37-8 2-(1-Benzenesulfonyl-3-methyl-1H-indol-2-yl)-1,1,1-trifluoro-propan-2-ol 
• 79663-87-9 1-(3-trifluoromethylphenyl)-1-(trifluoromethyl)ethanol 
• 79247-86-2 4-trifluoromethylthiazole-2-carboxylic acid ethyl ester 
• 1630-78-0 (E)-1,2-difluoroethene 
• 75995-83-4 r-2-trifluoromethyl-2-methyl-t-3,t-4-difluoro-oxetan 

Relevant articles and documents

SYNTHESIS AND CRYSTAL STRUCTURE OF 1,1,1,5,5,5-HEXAFLUORO-2-AMINOPENTAN-4-ONE (HFAP)

The vapour phase reaction of ammonia and hexafluoroacetylacetone leads to the formation of the new β-keto-amine C5H3F6NO.Crystals of the compound are monoclinic, space group P21/n, a = 10.01(2), b = 19.33(3), c = 8.40(1) Angstroem, β = 82.27(6) deg; final R = 0.044.

One electron transfer chain decomposition of trifluoroacetone diperoxide: The first 1,2,4,5-tetroxane with O-transfer capability

Reaction of 1,1,1-trifluoropropanone (trifluoroacetone) (1a) with 30% hydrogen peroxide in the presence of conc. sulfuric acid afforded in good yield 3,6-bis(trifluoromethyl)-3,6-dimethyl-1,2,4,5-tetroxane or trifluoroacetone diperoxide (2a). Peroxide 2a is quantitatively converted into trifluoroacetone (1a) and dioxygen by a catalytic amount of tetrabutylammonium iodide through a reductive electron transfer chain reaction carried out by the superoxide ion. Trifluoroacetone diperoxide (2a) is capable of O-atom transfer to alkenes and sulfides.

Homogeneous liquid-liquid extraction of neodymium(iii) by choline hexafluoroacetylacetonate in the ionic liquid choline bis(trifluoromethylsulfonyl)imide

The ionic liquid choline bis(trifluoromethylsulfonyl)imide, [Chol][Tf 2N], was used for the extraction of neodymium(iii), in combination with choline hexafluoroacetylacetonate, [Chol][hfac], as the extractant. The binary mixture of [Chol][Tf2N] and water shows temperature-dependent phase behavior, with an upper critical solution temperature of 72 °C. A novel extraction technique, homogeneous liquid-liquid extraction (HLLE), was applied to this solvent system. HLLE is based on the use of thermomorphic solvent mixtures and has the advantage of forming a homogeneous phase during mixing. Extraction is not kinetically hindered by an interface and the extraction equilibrium is reached faster than in the case of heterogeneous mixing in conventional solvent extraction. Several extraction parameters were studied for the extraction of neodymium(iii) with [Chol][hfac]: temperature, pH, extractant concentration and loading of the ionic liquid phase. A speciation study was performed to determine the stoichiometry of the extracted neodymium(iii) complex and a plausible extraction mechanism is proposed. Neodymium is extracted as a tetrakis hexafluoroacetylacetonate complex with one choline cation as counter ion. The crystal structure of the extracted complex showed the presence of a coordination bond between the choline counter ion and the neodymium(iii) center, resulting in a coordination number of nine. The stripping of the loaded neodymium and the influence of acid and extractant concentrations on the phase behavior of the [Chol][Tf2N]-H 2O system were investigated. This journal is the Partner Organisations 2014.

One-electron reduction of methyl(trifluoromethyl)dioxirane by iodide ion. Evidence for an electron-transfer chain reaction mediated by the superoxide ion

One-electron-transfer processes, triggered by I- in catalytic amounts, convert methyl(trifluoromethyl)dioxirane (1) into 1,1,1-trifluoropropanone (trifluoroacetone) and dioxygen. It is proposed that the initially formed bis(oxy)methylene radical anion 1′ performs nucleophilic attack at the dioxirane 1, yielding a dimeric radical anion 2′; the latter then fragments into trifluoroacetone and superoxide ion (O2?-). The intermediacy of Superoxide ion (the propagator of the electron-transfer chain reaction) is demonstrated by its trapping with either benzoyl chloride or chlorotrimethylsilane. Also, potassium superoxide in catalytic amounts induces the fast and complete conversion of 1 into trifluoroacetone with evolution of dioxygen. The redox reaction between dioxirane 1 and iodide ion in acidic medium yields substantial amounts of hydrogen peroxide, which was detected by the catalase probe.

Eliminations from 2H-Heptafluorobut-2-ene

Various approaches are described for dehydrofluorination of heptafluorobut-2-ene (2) to give hexafluorobut-2-yne (1). Molecular sieve is particularly successful. Reaction of (2) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) surprisingly gave the novel heterocycle (8) via initial nucleophilic attack. Reactions of (2) with other bases are also described.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

METHODS FOR FUNCTIONALIZATION HYDROCARBONS

In one aspect, the disclosure relates to a method for functionalizing hydrocarbons. In a further aspect, the method involves heating a hydrocarbon with a composition having an acid and an oxidant. In other aspects, the composition can further include an iodine-based compound and/or a compound having formula AaXn. In any of these aspects, the oxidant can be regenerated in situ or in a separate regeneration step. Also disclosed are functionalized hydrocarbons produced by the disclosed method. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

Catalytic conversion of ketones to esters: Via C(O)-C bond cleavage under transition-metal free conditions

The catalytic conversion of ketones to esters via C(O)-C bond cleavage under transition-metal free conditions is reported. This catalytic process proceeds under solvent-free conditions and offers an easy operational procedure, broad substrate scope with excellent selectivity, and reaction scalability. This journal is