133512-60-4

Basic information

• Product Name: Benzoic acid, 4-(pentafluoroethyl)-, ethyl ester
• CAS NO: 133512-60-4
• Molecular Formula: C11H9F5O2
• Molecular Weight: 268.183
• Mol File: 133512-60-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-(pentafluoroethyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(pentafluoroethyl)-, ethyl ester(133512-60-4)
• EPA Substance Registry System: Benzoic acid, 4-(pentafluoroethyl)-, ethyl ester(133512-60-4)

Safety Data

• Hazardous Substances Data: 133512-60-4(Hazardous Substances Data)

Upstream product

• 5798-75-4 Ethyl 4-bromobenzoate 
• 124898-13-1 trimethyl(pentafluoroethyl)silane 
• 60007-39-8 pentafluoroethylcopper(I) 
• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 94-09-7 p-aminoethylbenzoate 
• 116-14-3 polytetrafluoroethylene 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 4334-88-7 p-ethoxycarbonylphenylboronic acid 

Downstream Products

• 383-13-1 4-pentafluoroethylbenzoic acid 

Relevant articles and documents

Pentafluoroethylation of Arenediazonium Tetrafluoroborates Using On-Site Generated Tetrafluoroethylene

Copper-mediated pentafluoroethylation of arenediazonium tetrafluoroborates with tetrafluoroethylene (TFE) on-site generated from TMSCF3 has been developed as a new method to prepare pentafluoroethyl arenes. The active pentafluoroethylation reagent “CuC2F5” is pre-generated from CuSCN, TFE and CsF, and its generation and further reaction are strongly solvent-dependent. This pentafluoroethylation reaction represents the first example of Sandmeyer-type pentafluoroethylation, which exhibits good functional group tolerance and potential applications for the synthesis of complicated bioactive compounds.

From C1 to C2: TMSCF3 as a Precursor for Pentafluoroethylation

A highly efficient copper-mediated aromatic pentafluoroethylation method using TMSCF3 as the sole fluoroalkyl source is described. The reaction proceeds by a key C1 to C2 process, that is, the generation of CuCF3 from TMSCF3, followed by a subsequent spontaneous transformation into CuC2F5. Various aryl iodides were pentafluoroethylated with the TMSCF3-derived CuC2F5. This method represents the first practical and efficient method for pentafluoroethylation of aryl iodides using commercially available TMSCF3 as a pentafluoroethyl precursor.

Pentafluoroethylbenziodoxole (BIX-C2F5): A Shelf-Stable Reagent for Pentafluoroethylation of β-Ketoesters and Arylboronic Acids

An improved method for the preparation of pentafluoroethylating reagent pentafluoroethyl-substituted benziodoxole (BIX-C2F5) was described. Under mild conditions, BIX-C2F5was able to react with β-ketoesters or aryl/heteroaryl boronic acids to generate pentafluoroethylated compounds in good yields.