131079-13-5

Basic information

• Product Name: Hexanal, 2-[(dimethylphenylsilyl)methylene]-, (2Z)-
• CAS NO: 131079-13-5
• Molecular Formula: C15H22OSi
• Molecular Weight: 246.425
• Mol File: 131079-13-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Hexanal, 2-[(dimethylphenylsilyl)methylene]-, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexanal, 2-[(dimethylphenylsilyl)methylene]-, (2Z)-(131079-13-5)
• EPA Substance Registry System: Hexanal, 2-[(dimethylphenylsilyl)methylene]-, (2Z)-(131079-13-5)

Safety Data

• Hazardous Substances Data: 131079-13-5(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 201230-82-2 carbon monoxide 
• 766-77-8 Dimethylphenylsilane 
• 693-02-7 hex-1-yne 

Downstream Products

• 1070-66-2 2-n-butylacrolein 
• 622383-01-1 2-[(dimethylphenylsilyl)methylene]hexan-1-ol 
• 30857-70-6 2-benzylhexanal 

Relevant articles and documents

Rhodium-catalyzed intermolecular silylcarbamoylation of acetylenic bonds

α,β-Unsaturated amides are readily formed by silylcarbamoylation of an acetylenic bond which is accomplished intermolecularly by a one-pot reaction of four components, an alkyne, a hydrosilane, an amine, and CO in the presence of a catalytic amount of Rh

Silylformylation catalyzed by Rh and Rh-Co mixed metal complexes and its application to the synthesis of pyrrolizidine alkaloids

Reactions of hydrosilanes with 1-hexyne catalyzed by Co2Rh2(CO)12, Rh4(CO)12, (BuNC)4RhCo(CO)4, and Rh(acac)(CO)2 at 25°C and atmospheric pressure to 10 atm of carbon

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.

New synthesis of α-benzylaldehydes from 2-(dimethylphenylsilylmethylene)alkanals by fluoride promoted phenyl migration

α-Benzyl aldehydes are prepared from easily available β-silylalkenals and fluoride reagents, under mild experimental conditions; the reaction occurs instantaneously with almost quantitative yields. A plausible mechanism is suggested, which involves a 1,2-