272128-06-0

Basic information

• Product Name: 3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE
• Synonyms: 3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE
• CAS NO: 272128-06-0
• Molecular Formula: C5H6F3NO
• Molecular Weight: 153.1
• Mol File: 272128-06-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 186
• Flash Point: 66°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 0.695mmHg at 25°C
• Refractive Index: 1.349
• CAS DataBase Reference: 3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE(272128-06-0)
• EPA Substance Registry System: 3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE(272128-06-0)

Safety Data

• Hazard Codes: T
• Hazardous Substances Data: 272128-06-0(Hazardous Substances Data)

Usage

General Description

3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE is a chemical compound with the molecular formula C5H4F3NO. It is a colorless liquid with a faint odor, and is commonly used as an intermediate in the production of pharmaceuticals and agrochemicals. This chemical is known to be toxic if ingested, inhaled or absorbed through the skin, and can cause irritation to the eyes, skin, and respiratory system. It is also considered to be harmful to aquatic life and may have long-term adverse effects in the environment. Therefore, proper handling and disposal of 3-(2,2,2-TRIFLUOROETHOXY)PROPIONITRILE is necessary to minimize potential risks to human health and the environment.

InChI:InChI=1/C5H6F3NO/c6-5(7,8)4-10-3-1-2-9/h1,3-4H2

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 107-13-1 acrylonitrile 

Relevant articles and documents

Hydroamination and alcoholysis of acrylonitrile promoted by the pincer complex {κP,κC,κP-2,6- (Ph2PO)2C6H3}Ni(OSO 2CF3)

This report describes the catalytic activity of the pincer-type complex {κP,κC,κP-2,6-(Ph 2PO)2C6H3}Ni(OSO2CF 3) (1) in the anti-Markovnikov addition of aliphatic and aromatic amines and alcohols to acrylonitrile, crotonitrile, and methacrylonitrile. The influence of additives on the catalytic activities was investigated, and it was found that substoichiometric quantities of water promoted the C-N bond forming reactions catalyzed by 1, especially the reactions involving aromatic amines; in comparison, NEt3 had a less dramatic impact. The opposite pattern was observed for the alcoholysis of acrylonitrile promoted by 1: water had no beneficial effect on these reactions, while NEt3 proved to be a potent promoter. Another important difference between these reactions is that hydroamination works better with more nucleophilic amines, whereas the alcoholysis reactions work well with ArOH, CF3CH2OH, and ArCH2OH but not at all with the more nucleophilic aliphatic alcohols methanol, ethanol, and 2-propanol. Both hydroamination and alcoholysis proceed much better with acrylonitrile in comparison to its Me-substituted derivatives crotonitrile and methacrylonitrile. Under optimized conditions, precatalyst 1 promotes conjugate additions to acrylonitrile with catalytic turnover numbers of up to 100 (hydroamination) or higher (alcoholysis). Spectroscopic studies have established that the main Ni-containing species in the hydroamination reactions is a cationic adduct in which the olefinic substrate is bound to the Ni center via its nitrile moiety; this binding activates the double bond toward an outer-sphere nucleophilic attack by the amine (Michael addition). The solid-state structures of the cationic nitrile adducts [{κP, κC,κP-2,6-(Ph2PO)2C 6H3}Ni(NCR)][OSO2CF3] (R = Me (2a), CH2CH2N(H)Ph (2e)), which can be regarded as model complexes for the species involved in the hydroamination catalysis, have been elucidated. Also reported are the solid-state structures of the charge-neutral compound {κP,κC,κP-2,6-(i- Pr2PO)2C6H3}Ni(OSO 2CF3) and an octahedral Ni(II) species resulting from the aerobic/hydrolytic oxidation of 1.