72559-36-5

Usage

Molecular Structure

A benzene ring with a methoxy group (-OCH3) attached to the third carbon atom and a but-3-yn-1-yl group attached to the first carbon atom.

Physical State

Colorless liquid

Odor

Sweet, floral

Flammability

Highly flammable

Applications

a. Precursor in the production of pharmaceuticals, dyes, and fragrances
b. Solvent in chemical reactions and manufacturing processes

Safety Precautions

Handle with caution due to flammability and potential health hazards.

Upstream product

• 106-96-7 propargyl bromide 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 40138-66-7 3-(m-methoxyphenyl)propanal 
• 60190-80-9 dimethyl (1-diazo-2-oxo-2-phenylethyl)phosphonate 
• 189812-98-4 [4-(3-Methoxy-phenyl)-but-1-ynyl]-trimethyl-silane 
• 104997-02-6 3-(3-bromo-but-3-enyl)-anisole 

Downstream Products

• 1332955-35-7 6-(3-methoxyphenyl)hex-3-yn-1-ol 
• 1332955-43-7 C₁₃H₁₉NO 
• 1332955-44-8 C₁₃H₁₉NO 
• 1332955-49-3 C₁₅H₂₀O₂S 
• 1332954-72-9 (Z)-6-(3-methoxyphenyl)hex-3-en-1-ol 
• 1332955-50-6 C₁₅H₂₀O₂S 
• 1332954-93-4 (E)-N-(6-(3-methoxyphenyl)hex-3-enyl)-4-methylbenzenesulfonamide 
• 1332954-94-5 (Z)-N-(6-(3-methoxyphenyl)hex-3-enyl)-4-methylbenzenesulfonamide 
• 1332955-15-3 (E)-6-(3-methoxyphenyl)hex-3-ene-1-thiol 
• 1332955-16-4 (Z)-6-(3-methoxyphenyl)hex-3-ene-1-thiol 
• 1332954-71-8 (E)-6-(3-methoxyphenyl)hex-3-en-1-ol 
• 1353371-41-1 C₂₀H₂₄O₄S 

Relevant academic research and scientific papers

Tandem Prins/friedel-crafts cyclization for stereoselective synthesis of heterotricyclic systems

Homoallylic substrates such as (E)-6-arylhex-3-enyl alcohols, N-tosylamides, and thiols undergo smooth cross-coupling with various aldehydes in the presence of 10 mol % Sc(OTf)3 and 30 mol % TsOH to afford the trans-fused hexahydro-1H-benzo [f]isochromenes, N-tosyloctahydrobenzo [f] -isoquinolines, and hexahydro-lH-benzo [f]isothiochromenes, respectively. However, the cross-coupling of (Z)-olefins such as 6-arylhex-3-enyl alcohols, N-tosylamides, and thiols with aldehydes affords the corresponding hexahydro-1H-benzo-[f]isochromenes, N-tosyloctahydrobenzo [f]isoquinolines, and hexahydro-1H-benzo[f] isothiochromenes with complete cis selectivity via intramolecular Prins-, aza-Prins-, and thia-Prins/(Figure presented) Friedel - Crafts cyclizations, respectively. Though the Prins cyclization proceeds smoothly under the influence of Sc(OTf)3, high conversions and enhanced reaction rates are achieved using a mixture of Sc(OTf)3 and TsOH (1:3).

A convenient reagent for aldehyde to alkyne homologation

A convenient reagent for the one-carbon homologation of an aldehyde to the corresponding alkyne is reported. This reagent allows this conversion to conveniently be carried out on a large scale under ambient conditions.

Bronsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes

We have described the first Bronsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate. Copyright