155908-58-0

Basic information

• Product Name: 3-(2,2,2-trifluoroethoxy)benzaldehyde
• Synonyms: 3-(2,2,2-trifluoroethoxy)benzaldehyde;benzaldehyde, 3-(2,2,2-trifluoroethoxy)-
• CAS NO: 155908-58-0
• Molecular Formula: C₉H₇F₃O₂
• Molecular Weight: 204.1458896
• Mol File: 155908-58-0.mol

Chemical Properties

• Boiling Point: 230.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.292±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3-(2,2,2-trifluoroethoxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,2,2-trifluoroethoxy)benzaldehyde(155908-58-0)
• EPA Substance Registry System: 3-(2,2,2-trifluoroethoxy)benzaldehyde(155908-58-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 155908-58-0(Hazardous Substances Data)

Upstream product

• 6226-25-1 2,2,2-trifluoroethyl trifluoromethanesulphonate 
• 100-83-4 meta-hydroxybenzaldehyde 
• 587-04-2 m-Chlorobenzaldehyde 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 

Downstream Products

• 903630-07-9 (3-(2,2,2-trifluoroethoxy)phenyl)methanamine 
• 263349-56-0 (3-phenoxy-phenyl)-[3-(2,2,2-trifluoro-ethoxy)-benzyl]-amine 

Relevant articles and documents

ALCOHOL DERIVATIVES AS KV7 POTASSIUM CHANNEL OPENERS FOR USE IN EPILEPSY OR SEIZURES

The present invention provides novel compounds which activate the Kv7 potassium channels. Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds to treat disorders responsive to the activation of Kv7 potassium channels.

ALCOHOL DERIVATIVES AS KV7 POTASSIUM CHANNEL OPENERS

The present invention provides novel compounds which activate the Kv7 potassium channels. Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds to treat disorders responsive to the activation of Kv7 potassium channels.

ALCOHOL DERIVATIVES AS KV7 POTASSIUM CHANNEL OPENERS

The present invention provides novel compounds which activate the Kv7 potassium channels. Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds to treat disorders responsive to the activation of Kv7 potassium channels.

ALCOHOL DERIVATIVES AS KV7 POTASSIUM CHANNEL OPENERS

The present invention provides novel compounds which activate the Kv7 potassium channels. Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds to treat disorders responsive to the activation of Kv7 potassium channels.

Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

A simple and convenient method was developed for the introduction of a 2,2,2-trifluoroethoxy group to various aromatic and heteroaromatic systems. The novel process utilizes aromatic chlorides as substrates, and tetrakis(2,2,2-trifluoroethoxy) borate salt as an inexpensive and readily available fluoroalkoxy source in a palladium-catalyzed cross-coupling reaction. The power of the developed methodology was demonstrated in the synthesis of a fluorous derivative of Sildenafil.

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.