143142-90-9

Basic information

• Product Name: R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97
• Synonyms: R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97;(2R)-2-(Trifluoromethyl)oxirane (ee);(2R)-(+)-3,3,3-Trifluoro-1,2-propenoxide;(2R)-2-(Trifluoromethyl)oxirane, (2R)-1,2-Epoxy-3,3,3-trifluoropropane;(2R)-2-(trifluoromethyl)oxirane
• CAS NO: 143142-90-9
• Molecular Formula: C₃H₃F₃O
• Molecular Weight: 112.0505296
• Mol File: 143142-90-9.mol

Chemical Properties

• Boiling Point: 25-32 °C
• Flash Point: -15 °F
• Appearance: white crystal powder
• Density: 1.294 g/mL at 25 °C
• Vapor Pressure: 560mmHg at 25°C
• Refractive Index: n20/D <1.300
• Storage Temp.: 2-8°C
• CAS DataBase Reference: R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97(CAS DataBase Reference)
• NIST Chemistry Reference: R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97(143142-90-9)
• EPA Substance Registry System: R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97(143142-90-9)

Safety Data

• Hazard Codes: F+
• Statements: 12
• Safety Statements: 3
• RIDADR: UN 1993 3/PG 1
• WGK Germany: 3
• Hazardous Substances Data: 143142-90-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97 is used as a substrate for the synthesis of substituted trifluoro amino propanols, which are potent inhibitors of cholesteryl ester transfer protein. These inhibitors play a crucial role in managing cholesterol levels and can be used in the treatment of cardiovascular diseases.
Used in Chiral Synthesis:
R-(+)-2-TRIFLUOROMETHYLOXIRANE, 97 is used as a starting material for the preparation of (2R) Trifluoro-(methoxybenzyloxy)-propanol (chiral glycol) by reacting with 4-methoxybenzyl alcohol in the presence of NaH. This chiral glycol intermediate is further utilized in the synthesis of trifluoromethyl glycol carbamates, which have potential as monoacylglycerol lipase (MAGL) inhibitors. MAGL inhibitors can be used in the treatment of various conditions, including pain, inflammation, and neurodegenerative diseases.

InChI:InChI=1/C3H3F3O/c4-3(5,6)2-1-7-2/h2H,1H2/t2-/m1/s1

Upstream product

• 431-35-6 3-bromo-1,1,1-trifluoroacetone 
• 137429-44-8 3-bromo-1,1,1-trifluoropropan-2-ol 
• 359-41-1 1,1,1-trifluoro-2,3-epoxypropane 

Downstream Products

• 1032187-44-2 (R)-1,1,1-trifluoro-3-((S)-2-(3-fluoro-5-(trifluoromethyl)phenyl)-2-(5-fluoropyridin-2-yl)-3-phenylpropylamino)propan-2-ol 
• 1615720-80-3 (R)-N-(6-(4-(4-fluorophenyl)-1-(1-(3,3,3-trifluoro-2-hydroxypropyl)piperidin-4-yl)-1H-imidazol-5-yl)imidazo[1,2-b]pyridazin-2-yl)isonicotinamide 
• 1615721-10-2 (R)-2-fluoro-N-(6-(4-(4-fluorophenyl)-1-(1-(3,3,3-trifluoro-2-hydroxypropyl)piperidin-4-yl)-1H-imidazol-5-yl)imidazo[1,2-b]pyridazin-2-yl)isonicotinamide 

Relevant articles and documents

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including neurological disorders (e.g., Dravet syndrome, epilepsy), pain, and neuromuscular disorders are also provided herein.

Method for Industrial Production of Optically Active Fluoroalkyl Ethylene Oxide

It is possible to produce an optically active fluoroalkyl chloromethyl alcohol with a high optical purity and a good yield by treating a fluoroalkyl chloromethyl ketone with a microorganism having an activity for asymmetrically reducing the ketone or an enzyme having the activity. Then, it is possible to obtain a fluoroalkyl ethylene oxide by treating the alcohol with a base. Industrial implementation of the production method of the present invention is easy.

PYRAZOLYLAMINOBENZIMIDAZOLE DERIVATIVES AS JAK INHIBITORS

The present invention provides compounds of the formula below (I'): where R, and R1-R3 are as described herein, methods of treating patients for certain types of autoimmune diseases and cancer, and processes for preparing the compounds.

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

JAK1 inhibitors

The present invention relates to certain benzimidazole compounds, or pharmaceutically acceptable salts thereof, that inhibit Janus kinase 1 (JAK1), pharmaceutical compositions comprising the compounds, and methods of using the compounds to treat certain types of cancer.

ISOSELECTIVE POLYMERIZATION OF EPOXIDES

The present invention provides novel bimetallic complexes and methods of using the same in the isoselective polymerization of epoxides. The invention also provides methods of kinetic resolution of epoxides. The invention further provides polyethers with high enantiomeric excess that are useful in applications ranging from consumer goods to materials.

NEW CHIRAL SALEN CATALYSTS AND METHODS FOR THE PREPARATION OF CHIRAL COMPOUNDS FROM RACEMIC EPOXIDES BY USING THEM

The present invention relates to new chiral salen catalysts and the preparation method of chiral compounds from racemic epoxides using the same. More specifically, it relates to new chiral salen catalysts that have high catalytic activity due to new molecular structures and have no or little racemization of the generated target chiral compounds even after the reaction is completed and can be also reused without catalyst regeneration treatment, and its economical preparation method to mass manufacture chiral compounds of high optical purity, which can be used as raw materials for chiral food additives, chiral drugs, or chiral crop protection agents, etc., using the new chiral salen catalysts.

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.

Chiral N,N-disubstituted trifluoro-3-amino-2-propanols are potent inhibitors of cholesteryl ester transfer protein

A novel series of substituted N-benzyl-N-phenyl-trifluoro-3-amino-2-propanols are described that reversibly inhibit cholesteryl ester transfer protein (CETP). Starting with screening lead 22, various structural features were explored with respect to inhibition of the CETP-mediated transfer of [3H] cholesterol from high-density cholesterol donor particles to low-density cholesterol acceptor particles. The free hydroxyl group of the propanol was required for high potency, since acylation or alkylation reduced activity. High inhibitory potency was also associated with 3-ether moieties in the aniline ring, and the highest potencies were exhibited by 3-phenoxyaniline analogues. Activity was substantially reduced by oxidation or substitution in the methylene of the benzylic group, implying that the benzyl ring orientation was important for activity. In the benzylic group, substitution at the 3-position was preferred over either the 2- or the 4-positions. Highest potencies were observed with inhibitors in which the 3-benzylic substituent had the potential to adopt an out of plane orientation with respect to the phenyl ring. The best 3-benzylic substituents were OCF2CF2H (42, IC50 0.14 μM in buffer, 5.6 μM in human serum), cyclopentyl (39), 3-iso-propoxy (27), SCF3 (67), and C(CF3)2OH (36). Separation of 42 into its enantiomers unexpectedly showed that the minor R(+) enantiomer 1a was 40-fold more potent (IC50 0.02 μM in buffer, 0.6 μM in human serum) than the major S(-) enantiomer 1b, demonstrating that the R-chirality at the propanol 2-position is key to high potency in this series. The R(+) enantiomer 1a represents the first reported acyclic CETP inhibitor with submicromolar potency in plasma. A chiral synthesis of 1a is reported.