2136-75-6 | (Formylmethylene)triphenylphosphorane

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$13.00	$9.00
10g	97%	in stock	$19.00	$14.00
25g	97%	in stock	$20.00	$14.00
100g	97%	in stock	$29.00	$20.00
500g	97%	in stock	$120.00	$84.00

Description

• Catalog Number: AD29833
• Chemical Name: (Formylmethylene)triphenylphosphorane
• CAS Number: 2136-75-6
• Molecular Formula: C20H17OP
• Molecular Weight: 304.3221
• MDL Number: MFCD00006994
• SMILES: O=CC=P(c1ccccc1)(c1ccccc1)c1ccccc1

Computed Properties

• Complexity: 344
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 22
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• XLogP3: 3.6

Upstream Synthesis Route

2-(Triphenylphosphoranylidene)acetaldehyde is a valuable reagent widely used in chemical synthesis as a versatile and powerful tool for the formation of carbon-carbon bonds. Its ability to act as a nucleophile in various reactions makes it a key component in the construction of complex organic molecules.This compound finds particular application in the Horner-Wadsworth-Emmons reaction, a commonly employed method for the synthesis of olefins. By reacting with carbonyl compounds, such as aldehydes or ketones, 2-(Triphenylphosphoranylidene)acetaldehyde generates α,β-unsaturated esters or acids, providing a straightforward route to a range of functionalized double bonds.Additionally, 2-(Triphenylphosphoranylidene)acetaldehyde plays a crucial role in the Petasis reaction, facilitating the synthesis of β-amino alcohols. Through its reactivity towards electrophiles, this reagent enables the formation of C-N bonds, offering a convenient approach to a variety of nitrogen-containing compounds.In summary, the use of 2-(Triphenylphosphoranylidene)acetaldehyde in chemical synthesis allows for the efficient construction of diverse organic molecules by serving as a key building block in the formation of carbon-carbon and carbon-nitrogen bonds.

Literature

• Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones.

  Bioorganic & medicinal chemistry 20110101

• Preparation and chemistry of phosphoranyl-derived iodanes.

  The Journal of organic chemistry 20030207