1977-87-3

Basic information

• Product Name: cyclohexanecarbonyl fluoride
• Synonyms: cyclohexanecarbonyl fluoride
• CAS NO: 1977-87-3
• Molecular Weight: 130.162
• Mol File: 1977-87-3.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: cyclohexanecarbonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexanecarbonyl fluoride(1977-87-3)
• EPA Substance Registry System: cyclohexanecarbonyl fluoride(1977-87-3)

Safety Data

• Hazardous Substances Data: 1977-87-3(Hazardous Substances Data)

Upstream product

• 2719-27-9 cyclohexanylcarbonyl chloride 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2043-61-0 cyclohexanecarbaldehyde 
• 100-49-2 cyclohexylmethyl alcohol 
• 80283-44-9 4-hydroxyphenyl cyclohexanecarboxylate 

Downstream Products

• 74598-74-6 cyclohex-1-en-1-yl(cyclohexyl)methanone 
• 22164-12-1 N-benzyl-N-methylcyclohexanecarboxamide 
• 35665-26-0 N-benzylcyclohexanecarboxamide 
• 7469-80-9 cyclohexyl 4-methoxyphenyl ketone 
• 79852-25-8 cyclohexyl(thiophen-2-yl)methanone 
• 111609-50-8 cyclohexyl(furan-2-yl)methanone 
• 69210-90-8 cyclohexyl-(2,5-dimethoxy-phenyl)-ketone 
• 22733-94-4 benzyl cyclohexanecarboxylate 
• 166331-85-7 fluoromethyl cyclohexanecarboxylate 

Relevant articles and documents

Selective Electrochemical Formyl Hydrogen-Exchange Fluorination of Aliphatic Aldehydes to Prepare Acyl Fluorides Using HF-Base Solutions

The selective displacement of formyl hydrogen to fluorine in aliphatic aldehydes was successfully carried out electrochemically to give acyl fluorides in base-nHF (base: pyridine or Et3N, n=3-6) electrolyte solution with or without solvents such as acetonitrile and sulfolane.

Radical-Mediated Activation of Esters with a Copper/Selectfluor System: Synthesis of Bulky Amides and Peptides

Herein, we describe a new approach for the activation of esters via a radical-mediated process enabled by a copper/Selectfluor system. A variety of para-methoxybenzyl esters derived from bulky carboxylic acids and amino acids can be easily converted into the corresponding acyl fluorides, directly used in the one-pot synthesis of amides and peptides. As a proof of concept, this method was applied to the iterative formation of sterically hindered amide bonds.

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.

N-Hydroxybenzimidazole as a structurally modifiable platform forN-oxyl radicals for direct C-H functionalization reactions

Methods for direct functionalization of C-H bonds mediated byN-oxyl radicals constitute a powerful tool in modern organic synthesis. While severalN-oxyl radicals have been developed to date, the lack of structural diversity for these species has hampered further progress in this field. Here we designed a novel class ofN-oxyl radicals based onN-hydroxybenzimidazole, and applied them to the direct C-H functionalization reactions. The flexibly modifiable features of these structures enabled facile tuning of their catalytic performance. Moreover, with these organoradicals, we have developed a metal-free approach for the synthesis of acyl fluoridesviadirect C-H fluorination of aldehydes under mild conditions.