(S)-1,1,1-TRIFLUORO-2-PROPANOL Property

Boiling point:

67.0±35.0℃ (760 Torr)

Density 

1.235±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

38.8±17.0℃

pka

12.53±0.20(Predicted)

form 

liquid

color 

Clear

Safety

RIDADR 

UN1993

HS Code 

2905599890

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

(S)-1,1,1-TRIFLUORO-2-PROPANOL Chemical Properties,Usage,Production

Description

(S)-1,1,1-Trifluoro-2-propanol is a compound important as an intermediate for various medicines and agrichemicals. Aside from methods using chemical catalysts, biological methods of reducing 1,1,1-trifluoroacetone to (S)-1,1,1-trifluoro-2-propanol by having microbial enzymes act on 1,1,1-trifluoroacetone has hitherto been studied.

Uses

(S)-1,1,1-TRIFLUORO-2-PROPANOL can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development and chemical production processes.

Uses

(S)-1,1,1-Trifluoro-2-propanol can be used as ion channel modulators to treat neurological disorders.

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).