(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
Uses Preparation- Product Name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- CAS No.
- 127852-28-2
- Chemical Name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- Synonyms
- C1oHgF6O;R-MBT-PEL;(R)-1-[3,5-Bis(trifL;Aprepitant Impurity 49;Phenol,5-iodo-4-methyl-;Fosaprepitant Impurity 25;Rolapitant Intermediate 3;Thiazole,2-bromo-9-methyl-;(R)-1-[3,5- Bis(trifluoromethyl)phenyl]et;(R)-BIS-3,5-TRIFLUOROMETHYL-1-PHENYLETHANOL
- CBNumber
- CB5113482
- Molecular Formula
- C10H8F6O
- Formula Weight
- 258.16
- MOL File
- 127852-28-2.mol
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol Property
- Melting point:
- 53-58℃
- Boiling point:
- 175.8±35.0 °C(Predicted)
- Density
- 1.376±0.06 g/cm3(Predicted)
- storage temp.
- -20°C Freezer
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly)
- pka
- 13.99±0.20(Predicted)
- form
- Powder
- color
- White
- optical activity
- [α]/D +27±1°, c = 1 in acetonitrile
- λmax
- 272nm(MeOH)(lit.)
- InChI
- InChI=1/C10H8F6O/c1-5(17)6-2-7(9(11,12)13)4-8(3-6)10(14,15)16/h2-5,17H,1H3/t5-/s3
- InChIKey
- MMSCIQKQJVBPIR-RXMQYKEDSA-N
- SMILES
- C(C1C=C([C@H](O)C)C=C(C(F)(F)F)C=1)(F)(F)F |&1:4,r|
- CAS DataBase Reference
- 127852-28-2(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36/37/38-52/53-22
- Safety Statements
- 26-36/37/39-61
- WGK Germany
- 3
- Hazard Note
- Irritant
- HS Code
- 29062990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 49554
- Product name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- Purity
- ≥98.0% (GC)
- Packaging
- 5g
- Price
- $72
- Updated
- 2023/06/20
- Product number
- 49554
- Product name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- Purity
- ≥98.0% (GC)
- Packaging
- 25g
- Price
- $216
- Updated
- 2023/06/20
- Product number
- B4131
- Product name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $59
- Updated
- 2025/07/31
- Product number
- B4131
- Product name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $192
- Updated
- 2025/07/31
- Product number
- B416125
- Product name
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol
- Packaging
- 25g
- Price
- $260
- Updated
- 2021/12/16
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol Chemical Properties,Usage,Production
Uses
(R)-[3,5-bis (trifluoromethyl) phenyl] ethanol is an important chiral intermediate for the synthesis of novel chemotherapeutic and antiemetic drugs NK-1 receptor antagonists. Antidepressants have good potential efficacy in treating a range of central and peripheral nervous system depressions.
Preparation
At present, the methods for preparing optically pure (R)-[3,5-bis (trifluoromethyl) phenyl] ethanol include chemical methods and biological methods. Chemical synthesis requires the use of expensive transition metal Ru and other chemical catalysts, complicated steps, harsh reaction conditions, high energy consumption, large pollution, and low yield. Biological law is the use of free enzymes or whole cells for catalytic preparation. It has the characteristics of mild reaction conditions, high catalytic efficiency, and strong specificity.
Chemical Properties
White fine crystalline powder
Uses
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol is an intermediate in the synthesis of Aprepitant (A729800), a novel selective neurokinin-1 (NK-1) receptor antagonist. In vitro studies using human liver microsomes indicate that Aprepitant is metabolised primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19, and no metabolism by CYP2D6, CYP2C9, or CYP2E1. Antiemetic.
General Description
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol is a key intermediate for the synthesis of aprepitant, a potent human neurokinin-1 (NK-1) receptor.
Synthesis
30071-93-3
7480-35-5
368-63-8
The general procedure for the synthesis of 1-[3,5-bis(trifluoromethyl)phenyl]ethanol from 3,5-bis(trifluoromethyl)phenylacetophenone and cis-1-amino-2,3-dihydro-1H-inden-2-ol was as follows: in Example 5, [RuCl2(p-cymene)]2 (18.4 g), (1S,2R)- cis-1-amino-2-inden-2-ol (9.0 g) and 1- (3,5-bis(trifluoromethyl)phenyl)ethan-1-one (3 kg) were dissolved in 2-propanol (21 L), stirred for 30 min and thoroughly degassed under vacuum. A 5M sodium hydroxide solution (28mL) was then added and the mixture was aged for 4-6 hours to ensure complete conversion of the feedstock. Upon completion of the reaction, the mixture was poured into 1N HCl (21L) and extracted with heptane (2 x 10.5L). The organic layers were combined, washed with brine, and 1,4-diazabicyclo[2.2.2]octane (740 g) was added. The solution was concentrated to nearly 4 mL/g of alcohol (KF < 200 μg/mL; 2-propanol < 5 vol%). The mixture was inoculated at 40°C and allowed to cool slowly to room temperature to form crystalline species, which were then further cooled to 0°C. The crystalline product was collected by filtration, washed with cold heptane and dried to give the DABCO complex in 75-80% yield and ee value >99%.
References
[1] Patent: US2002/22725, 2002, A1
[2] Patent: US2002/52493, 2002, A1
[3] Patent: US2002/52494, 2002, A1
[4] Patent: US6432952, 2002, B1
[5] Patent: US2003/215456, 2003, A1
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol Preparation Products And Raw materials
Raw materials
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View Lastest Price from (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol manufacturers
- Product
- (R)-1-[3,5-Bis(trilfuoromethyl)phenyl]ethanol 127852-28-2
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-12-09
- Product
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol 127852-28-2
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-27
- Product
- (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol 127852-28-2
- Price
- US $300.00-250.00/kg
- Min. Order
- 100kg
- Purity
- 99.99%
- Supply Ability
- 100Tons
- Release date
- 2023-03-06