20445-31-2

Basic information

• Product Name: (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid
• Synonyms: (R)-(+)-MTPA,(R)-(+)-Mosher'sacid;(R)-(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid, 99%(e.e.>99.5%);(+)--Methoxy--(trifluoromethyl)phenylaceticacid(Moshersacid);(r)-(+)-à-methoxy-à-(trifluoromethyl)phenylacetic acid;(R)-(+)-1-Methoxy-1-(trifluoromethyl)phenylacetic acid 99% (99%ee);(R)-(+)-1-Methoxy-1-(trifluoromethyl)phenylacetic acid (99%ee);(R)-(+)-ɑ-Methoxy-ɑ-(trifluoromethyl)phenylacetic acid, 99%;(R)-(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic Acid [Optical Resolving]
• CAS NO: 20445-31-2
• Molecular Formula: C₁₀H₉F₃O₃
• Molecular Weight: 234.17
• EINECS: 243-829-5
• Product Categories: Analytical Chemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination
• Mol File: 20445-31-2.mol

Chemical Properties

• Melting Point: 46-49 °C(lit.)
• Boiling Point: 105-107 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystalline Low Melting Solid
• Density: 1.344 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol (50 mg/ 1 ml).
• PKA: 1.47±0.10(Predicted)
• Sensitive: Hygroscopic
• Merck: 14,6280
• BRN: 2215440
• CAS DataBase Reference: (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid(20445-31-2)
• EPA Substance Registry System: (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid(20445-31-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• HazardClass: IRRITANT, HYGROSCOPIC, KEEP COLD
• Hazardous Substances Data: 20445-31-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid is used as a chiral derivatizing agent for the determination of enantiomeric purity and absolute configuration of alcohols and amines by NMR. This is important for the development and quality control of chiral drugs, as the stereochemistry of a compound can significantly affect its biological activity and safety.
Used in Analytical Chemistry:
(R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid is used as a widely used reagent for the determination of optical purities of alcohols and amines by 1H or 19F NMR. This allows for the accurate measurement of the enantiomeric composition of chiral compounds, which is crucial in various fields such as pharmaceuticals, agrochemicals, and fragrances.
Used in Research:
(R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid is used as a derivatization agent for β-arylethylamines, enantiomeric alcohols, and enantiomeric amines in research settings. This helps in the study of the stereochemistry and properties of these compounds, as well as their interactions with other molecules and biological systems.

InChI:InChI=1/C10H8ClF3O2/c1-16-9(8(11)15,10(12,13)14)7-5-3-2-4-6-7/h2-6H,1H3/t9-/m0/s1

Upstream product

• 67-56-1 methanol 
• 13006-19-4 α-(Chlordifluormethyl)-α-(trifluormethyl)-benzylalkohol 
• 141090-95-1 Trimethyl-(2,2,2-trichloro-1-phenyl-1-trifluoromethyl-ethoxy)-silane 
• 80866-87-1 α-methoxy-α-trifluoromethyl-phenyl-acetonitrile 
• 105678-40-8 (2RS)-2-Methoxy-2-trifluoromethylphenylacetamide 
• 145938-92-7 1,1,1-Trichloro-3,3,3-trifluoro-2-phenyl-propan-2-ol 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 111688-22-3 (R)-(-)-α-methoxy-α-trifluoromethylphenylacetyl chloride 
• 120576-70-7 (R)-MTPA 
• 20445-31-2 MTPA 
• 39532-38-2 (1R,2S,5R)-menthyl (R)-α-methoxy-α-trifluoromethylphenylacetate 
• 537695-87-7 (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanol 
• 384-64-5 3,3,3-trifluoro-2-phenylpropene 
• 159383-84-3 (-)-(2R)-3,3,3-trifluoro-2-phenylpropane-1,2-diol 

Downstream Products

• 111042-72-9 (2S)-2,3-dimethylbutyl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 17257-71-5 (S)-Mosher acid 
• 1044203-86-2 pentafluorophenyl trifluoromethyl-methoxy-phenylacetate 
• 76904-97-7 3-(S)-3-[2-(R)-2-methoxy-2-phenyl-2-trifluoromethyl]acetoxybutyric acid methyl ester 
• 127604-11-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-methyl-2-phenylcarbamoyl-ethyl ester 
• 127604-10-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methyl-2-phenylcarbamoyl-ethyl ester 
• 79644-02-3 (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 85718-78-1 (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate 

Relevant articles and documents

Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones

The first catalytic asymmetric vinylogous aldol reaction of activated allyls to activated acyclic ketones is disclosed. A variety of activated acyclic ketones, such as trifluoromethyl ketones, α-ketoesters, and α-keto phosphonates, were found to be involved forming diverse γ-selective aldol adducts with high enantioselectivities (up to >99% ee). The method provides an effective, general strategy to access valuable chiral electron-withdrawing group-substituted tertiary hydroxyl-based carboxylic acids.

Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched α-Hydroxy-α-perfluoroalkyl Esters

This study has led to the development of a novel, highly efficient, 1,2-perfluoro-alkyl/-aryl migration process in reactions of hydrate of 1-perfluoro-alkyl/-aryl-1,2-diketones with alcohols, which are promoted by a Zn(II)/bisoxazoline and form α-perfluoro-alkyl/-aryl-substituted α-hydroxy esters. With (-)-8-phenylmenthol as the alcohol, the corresponding menthol esters are generated in high yields with excellent levels of diastereoselectivity. The mechanistic studies show that the benzilic ester-type rearrangement reaction takes place via an unusual 1,2-migration of electron-deficient trifluoromethyl group rather than the phenyl group. The overall process serves as a novel, efficient, and simple approach for the synthesis of highly enantioenriched, biologically relevant α-hydroxy-α-perfluoroalkyl carboxylic acid derivatives.

Thioacids and thioacid salts for determining the enantiomeric excess of chiral compounds containing an electrophilic carbon center

The invention provides novel chiral compounds including 2-methoxy-2-trifluoromethylphenylacetic thioacid useful to react with and analyze other chiral compounds that have an electrophilic chiral carbon center.

Probing the parallel resolution of Mosher's acid using a combination of quasi-enantiomeric oxazolidin-2-ones

Mosher's acid (2-methoxy-2-phenyl-2-trifluoromethylacetic acid) was resolved by parallel resolution of its corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of oxazolidin-2-ones.

Synthetic application of 3,3-dichloro-1, 1, 1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1, 1, 1-trifluoroacetone (TCTFA) for trifluorolactic acid derivatives

Synthetic application of 3,3-dichloro-1,1,1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1,1,1-trifluoroacetone (TCTFA) for industrially important trifluorolactic acid derivatives is described. Trifluorolactic acid was obtained by hydrolysis of DCTFA unde

Enantioselective synthesis of arylmethoxyacetic acid derivatives

The preparation of several arylmethoxyacetic acids by a sequence of asymmetric dihydroxylation and further oxidation of the resulting glycol with TEMPO/NaClO/NaClO2 is described. The scope and limitations of the reaction are discussed.

An effective hydrolysis of crowded chiral esters

Trifluoromethanesulfonic acid-coated silica in the absence of solvents is an effective reagent for hydrolysis of sterically crowded chiral esters giving chiral acids in good chemical and optical yield. On the other hand, the method was unsuitable for the

Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network

Enantiopure cis-1-aminoindan-2-ol was selected as a basic resolving agent for racemic 2-arylalkanoic acids on the basis that its rigid cis-conformation would favor the formation of a supramolecular hydrogen-bonded column, in which chiral discrimination of the racemic carboxylate would occur. It was found that this amino alcohol possesses high resolving efficiency for a variety of racemic acids; also, X-ray crystallographic analyses of the diastereomeric salts showed that a columnar hydrogen-bond network is formed in both the less- and more-soluble diastereomeric salts, as we had expected. A detailed study on the stabilising interactions suggested that there are two that play an important role: (i) hydrogen bonding between the ammonium and hydroxy groups and the acid carboxylate, which determines the formation of the columnar network and (ii) CH...π, which influences the herringbone packing of the aromatic groups, implying that it also plays some role in chiral discrimination.

Stereoselective Synthesis of Trifluoromethylated Compounds: Nucleophilic Addition of Formaldehyde N,N-Dialkylhydrazones to Trifluoromethyl Ketones

The nucleophilic 1,2-addition of formaldehyde N,N-dialkylhydrazones 1, 2, and 7-10 to trifluoromethyl ketones 3a-e takes place in the absence of any catalyst or promoter to afford a series of α-hydroxy-α-trifluoromethylhydrazones (4, 5, and 11-14) in good-to-excellent yields. From the several reagents studied, optimal results were achieved using 1-(methyleneamino)pyrrolidine (2) for the synthesis of racemic adducts and (S)-l-(methyleneamino)-2-[1-(methoxy)diphenyl-methyl]-pyrrolidine (10) for the asymmetric version of the reaction. The resolving properties of the chiral auxiliary carried by 10 allowed an easy Chromatographic (flash) separation of any obtained diastereomeric mixture. Thus, a single operation rendered moderate-to-good amounts (42-75%) of optically pure adducts (S,S)-14 (de > 98%) by combining excellent chemical (82-92%) and moderate optical (51-81%) yields. Hydrazones 5 and (S,S)-14 were protected by benzylation [→ 16 and (SJS)-18] and then transformed into benzyl-protected α-trifluoromethyl cyanohydrins 21 by MMPP oxidative cleavage and into α-benzyloxy-a-trifluoromethyl aldehydes 22 by ozonolysis. Alternatively, adducts 5 and (S,S)-14 were methylated [→ 19 and (S,S)-20] and transformed into the corresponding α-methoxy-α-trifluoromethyl carboxylic acids 24 by successive ozonolysis and in situ oxidation (NaClO2, tBuOH, isobutene) of the crude a-methoxyaldehydes.