154851-69-1

Basic information

• Product Name: Pentanal, 2-[(dimethylphenylsilyl)methylene]-3-methyl-, (2Z)-
• CAS NO: 154851-69-1
• Molecular Formula: C15H22OSi
• Molecular Weight: 246.425
• Mol File: 154851-69-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Pentanal, 2-[(dimethylphenylsilyl)methylene]-3-methyl-, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanal, 2-[(dimethylphenylsilyl)methylene]-3-methyl-, (2Z)-(154851-69-1)
• EPA Substance Registry System: Pentanal, 2-[(dimethylphenylsilyl)methylene]-3-methyl-, (2Z)-(154851-69-1)

Safety Data

• Hazardous Substances Data: 154851-69-1(Hazardous Substances Data)

Upstream product

• 922-59-8 3-methyl-1-pentyne 
• 201230-82-2 carbon monoxide 
• 766-77-8 Dimethylphenylsilane 
• 108-86-1 bromobenzene 

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.

Silylformylation of chiral 1-alkynes, catalysed by solvated rhodium atoms

Solvated rhodium atoms, prepared by the metal vapour synthesis technique, promote the silylformylation reaction of variously substituted alkynes R1R2CH(CH2)nC≡CH, with catalytic activities comparable with and even higher than more common species such as Rh4(CO)12. Z-Silylalkenals are exclusively formed in high yields (60-95%) indicating syn addition both of CO and of the silane (Me2PhSiH) to the triple bond. The chemoselectivity of the process (silylformylation vs. hydrosilylation) is highly affected by the amount of catalyst employed (mmol of Rh species with respect to the alkyne reagent), by the steric requirements of the acetylenic substrates and by the hydrosilane/alkyne molar ratio. When optically active acetylenes are treated in the presence of Me2PhSiH under carbon monoxide pressure, the silylformylation reaction occurs with total retention of stereochemistry of the stereogenic centre, even if it is at the α-position of the unsaturated moiety, to afford enantiomerically enriched β-silylalkenals.