3539-97-7

Basic information

• Product Name: (S)-1,1,1-TRIFLUORO-2-PROPANOL
• Synonyms: (2S)-1,1,1-trifluoro-2-propanol;(S)-Trifluoroisopropanol;(S)-1,1,1-Trifluoropropan-2-ol;(2S)-1,1,1-Trifluoropropan-2-ol;2-Propanol, 1,1,1-trifluoro-, (2S)-;(2S)-2-Hydroxy-1,1,1-trifluoropropane
• CAS NO: 3539-97-7
• Molecular Formula: C₃H₅F₃O
• Molecular Weight: 114.07
• Mol File: 3539-97-7.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 67.0±35.0℃ (760 Torr)
• Flash Point: 38.8±17.0℃
• Appearance: /
• Density: 1.235±0.06 g/cm3 (20 ºC 760 Torr)
• PKA: 12.53±0.20(Predicted)
• CAS DataBase Reference: (S)-1,1,1-TRIFLUORO-2-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,1,1-TRIFLUORO-2-PROPANOL(3539-97-7)
• EPA Substance Registry System: (S)-1,1,1-TRIFLUORO-2-PROPANOL(3539-97-7)

Safety Data

• RIDADR: UN1993
• Hazardous Substances Data: 3539-97-7(Hazardous Substances Data)

Usage

Description

(S)-1,1,1-Trifluoro-2-propanol is a significant compound that serves as an intermediate for the synthesis of various medicines and agrichemicals. It is characterized by its unique chemical structure, which includes a trifluoromethyl group and a hydroxyl group, making it a valuable building block in the pharmaceutical and chemical industries. (S)-1,1,1-TRIFLUORO-2-PROPANOL can be synthesized through different methods, including chemical catalysis and biological reduction using microbial enzymes acting on 1,1,1-trifluoroacetone.

Uses

Used in Pharmaceutical Industry:
(S)-1,1,1-Trifluoro-2-propanol is used as an organic synthesis intermediate for the development of new pharmaceutical compounds. Its unique structure allows for the creation of a wide range of drugs with potential therapeutic applications, making it a crucial component in the drug discovery process.
Used in Agrichemical Industry:
In the agrichemical sector, (S)-1,1,1-Trifluoro-2-propanol is utilized as an intermediate for the synthesis of various agrochemicals, such as pesticides and herbicides. Its incorporation into these products can enhance their effectiveness and selectivity, leading to improved agricultural outcomes.
Used in Laboratory Research and Development:
(S)-1,1,1-Trifluoro-2-propanol is also employed in laboratory settings for research and development purposes. Its unique properties make it an attractive candidate for studying various chemical reactions and exploring new synthetic pathways, contributing to the advancement of scientific knowledge in the field.
Used in Chemical Production Processes:
Lastly, (S)-1,1,1-Trifluoro-2-propanol plays a vital role in chemical production processes, where it is used as an intermediate to synthesize a variety of compounds. Its versatility and reactivity make it a valuable asset in the chemical manufacturing industry, facilitating the production of numerous products with diverse applications.

Synthesis

A liquid medium was prepared to be composed of 2000 ml of an ion-exchanged water, 60 g of glucose, 30 g of peptone, 50 g of yeast extract, 4.8 g of potassium dihydrogenphosphate and 2.5 g of dipotassium hydrogen phosphate. The liquid medium was charged into a fermenter of 5 L capacity (available from B.E. MARUBISHI Co., Ltd. under the trade name of a MDN-type 5L(S)) and then subjected to steam sterilization at 121°C for 60 minutes. This liquid medium was inoculated with 80 ml of a suspension of Hansenula polymorpha NBRC0799, the suspension being obtained by conducting a preliminary culture on 100 ml of the same composition to be 2.0 × 109 cfu/ml. Then, it was cultured at 28°C, an air ventilation of 1 vvm and a stirring speed of 500 rpm for 24 hours, thereby preparing a suspension of 4.3 × 109 cfu/ml (or 86 g/L in terms of the weight of wet cell bodies). At this time, adjustment of pH was attained by using aqueous ammonia, so that a pH was adjusted at 6.5. After culture had terminated, the ventilation amount and the stirring speed were changed to 0.1 vvm and 50 rpm. A solution obtained by dissolving 125.2 g of 1,1,1-trifluoroacetone and 200 g of glucose in 300 ml of an ion-exchanged water prepared in another vessel was added to the suspension automatically by a computer program in the use of an online sugar concentration sensor (an online biosensor available from ABLE & Biott Co.,Ltd. under the trade name of BF-410), so as to maintain a glucose concentration of 2 %. It was confirmed that the yield obtained after a lapse of 168 hours was 94.9 % by monitoring the reduction of the substrate due to the microorganism every 24 hours, upon which the reaction was terminated.In order to recall 1,1,1-trifluoro-2-propanol produced from the reaction solution after termination of the reaction, distillation was performed. A distillate was recalled in an amount of 188 ml, from which it was found, by internal standard method of 19F-NMR, that 109.2 g of 1,1,1-trifluoro-2-propanol was contained. As a result of measuring the optical purity under the above-discussed analyzing conditions, the optical purity was confirmed to be 98.7% ee (S-configuration).

Upstream product

• 421-50-1 1,1,1-trifluoro-2-propanone 
• 359-41-1 1,1,1-trifluoro-2,3-epoxypropane 
• 130025-34-2 (S)-2-trifluoromethyl-oxirane 
• 67-56-1 methanol 
• 374-01-6 1,1,1-trifluoroisopropanol 
• 18454-30-3 (+)-3-(1-trifluoromethylethoxy)propionic acid 
• 88378-50-1 (S)-(+)-1-Bromo-3,3,3-trifluoro-2-propanol 
• 143142-90-9 (2R)-2-(trifluoromethyl)oxirane 

Downstream Products

• 845616-82-2 5-methane-sulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid 
• 1224933-70-3 2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid 
• 1246442-51-2 carbonic acid 4-nitro-phenyl ester (S)-2,2,2-trifluoro-1-methyl-ethyl ester 
• 1252634-15-3 (2S,4R)-4-[2-Chloro-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzenesulfonyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl Ester 2-methyl Ester 
• 1364677-75-7 5-(4-chloro-3-(4-chloro-phenyl)-2-(S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine 
• 1364677-63-3 6-(4-chloro-phenyl)-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyrazine-2-carboxylic acid methyl ester 
• 1374674-98-2 4-{(S)-3-[2-chloro-4-((S)-2,2,2-trifluoro-1-methyl-1-ethoxy)-benzenesulfonyl]-pyrrolidin-1-yl}-6-trifluoromethyl-pyrimidine-2-carbonitrile 
• 1415818-02-8 (S)-1,1,1-trifluoropropan-2-yl 4-((1r,4r)-4-(3-cyanopyridin-4-yloxy)cyclohexyloxy)piperidine-1-carboxylate 
• 1434816-99-5 2-chloro-4-((S)-2,2,2-trifluoro-1-methylethoxy)-1-tritylsulfanyl benzene 
• 1430745-36-0 (1R,3S,5S)-((S)-1,1,1-trifluoropropan-2-yl) 3-((1r,4R)-4-(3-cyanopyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 1430747-24-2 (1R,3R,5S)-((S)-1,1,1-trifluoropropan-2-yl) 3-((1r,4R)-4-(3-cyanopyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 1434817-35-2 1-bromo-2-chloro-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzene 
• 1449329-77-4 tert-butyl 2-(5-chloro-3-fluoropyridin-2-yl)-2-((2S,4R)-4-(2-chloro-4-((S)-1,1,1-trifluoropropan-2-yloxy)phenylsulfonyl)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)azetidine-1-carboxylate 
• 1449329-76-3 tert-butyl 2-(5-chloro-3-fluoropyridin-2-yl)-2-((2S,4R)-4-(2-chloro-4-((S)-1,1,1-trifluoropropan-2-yloxy)phenylsulfonyl)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)azetidine-1-carboxylate 

Relevant articles and documents

ION CHANNEL MODULATORS

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.

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.

ION CHANNEL MODULATORS

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.