622382-74-5

Basic information

• Product Name: 2-[(dimethyl-p-tolylsilyl)methylene]hexanal
• Synonyms: 2-[(dimethyl-p-tolylsilyl)methylene]hexanal
• CAS NO: 622382-74-5
• Molecular Weight: 260.451
• Mol File: 622382-74-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[(dimethyl-p-tolylsilyl)methylene]hexanal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(dimethyl-p-tolylsilyl)methylene]hexanal(622382-74-5)
• EPA Substance Registry System: 2-[(dimethyl-p-tolylsilyl)methylene]hexanal(622382-74-5)

Safety Data

• Hazardous Substances Data: 622382-74-5(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 1432-39-9 dimethyl-p-tolylsilane 
• 693-02-7 hex-1-yne 
• 106-38-7 para-bromotoluene 

Relevant articles and documents

Fluoride-Promoted Rearrangement of Organo Silicon Compounds: A New Synthesis of 2-(Arylmethyl)aldehydes from 1-Alkynes

A new approach to 2-(arylmethyl)aldehydes 4 based upon a 1,2-anionotropic rearrangement of an aryl group is presented. The synthetic sequence begins with a silylformylation reaction of terminal acetylenes 5 with aryl and heteroaryl silanes 6, followed by treatment of the products (Z)-1 with TBAF. The optimization of the experimental conditions of the fluoride-promoted step is described, together with the synthetic potentialities of the process. A plausible mechanism of the rearrangement reaction is reported that suggests the addition of the fluoride ion to the arylsilicon moiety of β-silylalkenals (Z)-1 and the consequent migration of the aryl group to the adjacent carbon atom. Both aryl and heteroaryl substituents can rearrange without any loss of configuration. Bromofunctionalized substrates undergo an intramolecular reaction that affords exclusively carbacyclobenzyl aldehydes, further enhancing the high synthetic value of this method.