377-33-3

Basic information

• Product Name: TETRAFLUOROSUCCINIMIDE
• Synonyms: TETRAFLUOROSUCCINIMIDE;3,3,4,4-Tetrafluorosuccinimide;3,3,4,4-tetrafluoropyrrolidine-2,5-dione;3,3,4,4-tetrafluoropyrrolidine-2,5-quinone
• CAS NO: 377-33-3
• Molecular Formula: C4HF4NO2
• Molecular Weight: 171.05
• Mol File: 377-33-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 66-67°C
• Boiling Point: 176°C
• Flash Point: 68.2 °C
• Appearance: /
• Density: 1.7 g/cm³
• Vapor Pressure: 0.577mmHg at 25°C
• Refractive Index: 1.373
• PKA: 0.82±0.70(Predicted)
• CAS DataBase Reference: TETRAFLUOROSUCCINIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAFLUOROSUCCINIMIDE(377-33-3)
• EPA Substance Registry System: TETRAFLUOROSUCCINIMIDE(377-33-3)

Safety Data

• Hazard Codes: Xi,F
• Hazardous Substances Data: 377-33-3(Hazardous Substances Data)

Usage

General Description

Tetrafluorosuccinimide, also known as TFSI, is a chemical compound with the formula C4F4NO2. It is a white crystalline solid with a melting point of 116-117°C. TFSI is commonly used as a powerful and non-nucleophilic fluorinating agent in organic synthesis. It has been used as a reagent in the preparation of pharmaceuticals, agrochemicals, and other organic compounds. TFSI is also used as an electrolyte additive in lithium-ion batteries, as it can improve the cycling performance and thermal stability of the batteries. Additionally, it has potential applications in the field of ionic liquids and energy storage devices. TFSI is considered to be a versatile and useful compound in various chemical and industrial processes.

InChI:InChI=1/C4HF4NO2/c5-3(6)1(10)9-2(11)4(3,7)8/h(H,9,10,11)

Upstream product

• 425-08-1 Perfluor-bernsteinsaeure-monoamid 
• 377-37-7 2,2,3,3-tetrafluorosuccinamide 

Downstream Products

• 104710-88-5 trans-carbonyl(tetrafluorosuccinimidato-N)bis(triphenylphosphine)iridium 
• 104710-81-8 Pd(C₆H₅)(NCOC₂F₄CO)(P(C₆H₅)3)2 
• 104710-87-4 Rh(CO)(NCOC₂F₄CO)(P(C₆H₅)3)2 
• 104710-84-1 PdCl(NCOC₂F₄CO)((C₆H₅)2PC₂H₄P(C₆H₅)2) 
• 1810-13-5 (+/-)-3,3,4,4-tetrafluoropyrrolidine hydrochloride 

Relevant articles and documents

The chain carriers of intermolecular hydrogen abstraction in the photobromination with N-bromosuccinimide; modifications of the chain carriers

The photoinitiated bromination of 1-chloropentane with N-bromosuccinimide (NBS) in the presence of Br2 is compared with that of NBS and 1,1-dichloroethene to generate the succinimidyl radical (S radical) and with that of Br2 + K2CO3 to generate the bromine atom (Br radical) as the chain carriers.The relative reactivities of intermolecular H-abstraction (r-values) shown by the NBS + Br2 system decrease to levels lower than those shown by either S radical or Br radical chain propagations at lower temperatures under appropriate conditions: these observations indicate thepresence of a new chain propagating species that is assumed to be the bromine radical complex (BRC) modified from S radical or Br radical reversibly under the experimental conditions.Supporting evidence for the equilibria of S radical, Br radical, and BRC in the photodecomposition of NBS + Br2 is discussed.The unusual H-abstraction reactivity of Br radical toward the methyl hydrogens of 1-chloropentane was noted; this serves as independent support for the presence of a new radical propagation species.