173859-39-7

Basic information

• Product Name: 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile
• Synonyms: 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile
• CAS NO: 173859-39-7
• Molecular Formula: C₁₁H₈F₃NO
• Molecular Weight: 227.1825296
• Mol File: 173859-39-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 273.3°C at 760 mmHg
• Flash Point: 119.1°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 0.00577mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile(173859-39-7)
• EPA Substance Registry System: 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile(173859-39-7)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 173859-39-7(Hazardous Substances Data)

Usage

Description

1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile is a chemical compound characterized by its chemical formula C11H7F3NO. It is a white to light brown solid that is recognized for its high chemical reactivity. 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile is frequently utilized as a building block in the synthesis of pharmaceuticals and agrochemicals, and it also serves as a precursor in the production of other organic compounds. Its applications extend to research laboratories and industrial settings, where it is valued for its potential in the field of organic synthesis and drug discovery.

Uses

Used in Pharmaceutical Synthesis:
1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile is used as a building block for the synthesis of various pharmaceuticals. Its high chemical reactivity allows for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Production:
In the agrochemical industry, 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile is employed as a key component in the production of different agrochemicals. Its role in this sector is crucial for the development of effective products for agricultural use.
Used in Organic Synthesis:
1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile is used as a precursor in the field of organic synthesis. Its versatile chemical properties make it a valuable compound for creating a variety of organic molecules, which can be applied in numerous industries and research areas.
Used in Drug Discovery:
1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbonitrile is also utilized in drug discovery, where its reactivity and structural properties aid in the identification and development of potential new drugs. Its use in this field highlights the importance of chemical research and innovation in advancing medical treatments.

InChI:InChI=1/C11H8F3NO/c12-11(13,14)16-9-3-1-8(2-4-9)10(7-15)5-6-10/h1-4H,5-6H2

Upstream product

• 49561-96-8 (4-trifluoromethoxy-phenyl)-acetonitrile 
• 107-04-0 1-Bromo-2-chloroethane 
• 106-93-4 ethylene dibromide 

Downstream Products

• 936727-93-4 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarboxylic acid 
• 1239894-07-5 N-{(1S)-2-(3-amino-8-azabicyclo[3.2.1]oct-8-yl)-1-[(2,4-dichlorophenyl)methyl]-2-oxoethyl}-1-{4-[(trifluoromethyl)oxy]phenyl}cyclopropanecarboxamide 
• 1239707-77-7 (S)-ethyl 3-(4-bromophenyl)-2-(1-(4-(trifluoromethoxy)phenyl)cyclopropanecarboxamido)propanoate 
• 1373527-99-1 C₂₂H₂₀Cl₂F₃NO₄ 
• 1373527-88-8 (S)-3-(2,4-dichlorophenyl)-2-(1-(4-(trifluoromethoxy)phenyl)cyclopropanecarboxamido)propanoic acid 
• 1239707-78-8 (S)-3-(4-bromophenyl)-2-(1-(4-(trifluoromethoxy)phenyl)cyclopropanecarboxamido)propanoic acid 

Relevant articles and documents

Photochemical Deracemization at sp3-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer

A photochemical deracemization of 5-substituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80–99% ee). The reaction is catalyzed by a chiral diarylketone which displays a two-point hydrogen bonding site. Mechanistic evidence (DFT calculations, radical clock experiments, H/D labeling) suggests the reaction to occur by selective hydrogen atom transfer (HAT). Upon hydrogen binding, one substrate enantiomer displays the hydrogen atom at the stereogenic center to the photoexcited catalyst allowing for a HAT from the substrate and eventually for its conversion into the product enantiomer. The product enantiomer is not processed by the catalyst and is thus enriched in the photostationary state.

COMPOUNDS FOR TREATING AND PREVENTING GROWTH HORMONE RECEPTOR-DEPENDENT CONDITIONS

The invention relates to compounds, in particular pyrimidine-2,4-diamines, analogues and salts thereof and pharmaceutical compositions comprising pyrimidine-2,4-diamines analogues and salts thereof for use in the treatment and prevention of a disease, in particular a growth hormone receptor-dependent condition. The invention also relates to methods of using these compounds and compositions to treat physiological dsorders related to the amount or activity of growth hormone. In a particular embodiment, the invention relates to a compound according to formula 1 for use in the treatment or prevention of a disease in a subject

Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8- (trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury

Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure-activity studies in this series by branching at the α position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.