39637-99-5

Basic information

• Product Name: (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE
• Synonyms: (R)-(fi)-alpha-methoxy-alpha-trifluoromethylphenylacetylchloride;(+)-MTPA-CL;(+)-MOSHER'S ACID CHLORIDE;MOSHER'S ACID CHLORIDE;(+)-MOSHER'S CHLORIDE;(S)-(+)-A-METHOXY-A-(TRIFLUOROMETHYL)PHENYLACETYL CHLORIDE;(S)-(+)-ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)BENZENEACETYLCHLORIDE;(S)-(-)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE
• CAS NO: 39637-99-5
• Molecular Formula: C₁₀H₈ClF₃O₂
• Molecular Weight: 252.62
• EINECS: -0
• Product Categories: Analytical Chemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination
• Mol File: 39637-99-5.mol
• Article Data: 147

Chemical Properties

• Boiling Point: 213-214 °C(lit.)
• Flash Point: 194 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.35 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.469(lit.)
• Storage Temp.: −20°C
• Water Solubility: Sparingly miscible with water.
• Sensitive: Moisture Sensitive
• Merck: 14,6280
• BRN: 3591565
• CAS DataBase Reference: (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE(39637-99-5)
• EPA Substance Registry System: (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE(39637-99-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 39637-99-5(Hazardous Substances Data)

Usage

Description

(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE, also known as (R)-(-)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride, is a chiral acylating reagent with clear colorless to light yellow liquid properties. It plays a significant role in the resolution of amino acid enantiomers and the determination of the optical composition of compounds extracted from biological fluids.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE is used as a chiral acylating reagent for the resolution of amino acid enantiomers, such as 2,5-dimethoxy-4-methylamphetamine. This application is crucial in the development of enantiomerically pure drugs, which can have different pharmacological effects and reduce potential side effects caused by the unwanted enantiomer.
Used in Analytical Chemistry:
In the field of analytical chemistry, (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE is used for the determination of the optical composition of compounds extracted from biological fluids. This is important for understanding the stereochemistry of molecules and their interactions with biological systems, which can influence the efficacy and safety of drugs.
Used in Research and Development:
(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE is also utilized in research and development for the synthesis of novel chiral compounds and the study of their properties. This contributes to the advancement of knowledge in the field of stereochemistry and the development of new pharmaceuticals and materials with potential applications in various industries.

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

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• 17257-71-5 (-)-MTPA 
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Downstream Products

• 91487-22-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-methoxycarbonyl-1-thiophen-2-yl-propyl ester 
• 91487-22-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-2-methoxycarbonyl-1-thiophen-2-yl-propyl ester 
• 79847-80-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-2-methyl-decyl ester 
• 79847-80-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-methyl-decyl ester 
• 79847-80-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-methyl-decyl ester 
• 110884-73-6 (+)-(S)-m-nitrophenyl α-methoxy-α-trifluoromethylphenylacetate 
• 66050-95-1 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-(4-methyl-cyclohex-3-enyl)-propyl ester 
• 109121-09-7 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109121-07-5 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109064-53-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109121-08-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109214-45-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-2-methyl-3-oxo-2-propyl-cyclopentyl ester 
• 109121-05-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-2-methyl-3-oxo-2-propyl-cyclopentyl ester 
• 109064-52-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-methyl-3-oxo-2-propyl-cyclopentyl ester 

Relevant articles and documents

Synthesis, Absolute Configurations, and Biological Activities of Floral Scent Compounds from Night-Blooming Araceae

The uncommon jasmone derivatives dehydrojasmone, isojasmol, and isojasmyl acetate, floral scent compounds from night-blooming Araceae, were synthesized in a scalable synthesis employing conjugate addition with a selenoacetal as the key step. The stereoselective strategy with subsequent enzymatic kinetic resolution allowed determining the absolute configuration of the natural compounds by GC on a chiral phase. The homoterpene (E)-4,8-dimethyl-1,3,7-nonatrien-5-yl acetate, another uncommon scent compound, was obtained by α-regioselective aldehyde prenylation. The biological activities of dehydrojasmone and isojasmol were investigated in field assays, showing that these unique volatiles are able to selectively attract specific cyclocephaline scarab beetle pollinators.

Multigram Preparation of BRD4780 Enantiomers and Assignment of Absolute Stereochemistry

The development of a multigram synthesis of 3-exo-isopropylbicyclo[2.2.1]heptan-2-endo-amine hydrochloride (1) (also known as BRD4780 and AGN-192403) is described. The process involves protection of the amine as 4-nitrobenzyl carbamate, pNZ, which enables chiral SFC chromatography. The absolute configuration (AC) of the individual enantiomers has been determined by Mosher's amide method, VCD spectroscopy, and X-ray crystallography. We highlight the VCD approach as a rapid and effective means of AC determination that can be deployed directly on the target compounds.

Studies toward norzoanthamine: Ireland–Claisen rearrangements of α,β-unsaturated esters in a stereocontrolled synthesis of trans-fused 2-cyclohexen-1-ones

The enantiocontrolled preparation of the trans-fused ABC ring system of norzoanthamine is described. The synthesis strategy has incorporated studies of Ireland–Claisen rearrangements of esters derived from 3,3-dimethylacrylic acid. Stereocontrol results from competing chair- and boat-like transition states. Introduction of a nitroalkene by application of a modified Henry reaction facilitates an intramolecular Diels–Alder cycloaddition for an effective and simple transformation to the desired conjugated decalone. A fully functionalized AB ring system leads to the cyclization of the trans-fused cyclohexenone to complete the ABC system via ring-closing metathesis.