33553-90-1

Basic information

• Product Name: 2-Butynoic acid, 4-hydroxy-4-phenyl-, methyl ester
• CAS NO: 33553-90-1
• Molecular Formula: C11H10O3
• Molecular Weight: 190.199
• Mol File: 33553-90-1.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 2-Butynoic acid, 4-hydroxy-4-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butynoic acid, 4-hydroxy-4-phenyl-, methyl ester(33553-90-1)
• EPA Substance Registry System: 2-Butynoic acid, 4-hydroxy-4-phenyl-, methyl ester(33553-90-1)

Safety Data

• Hazardous Substances Data: 33553-90-1(Hazardous Substances Data)

Upstream product

• 4519-46-4 methyl 2-bromoacrylate 
• 100-52-7 benzaldehyde 
• 598-30-1 sec.-butyllithium 
• 594-19-4 tert.-butyl lithium 
• 109-72-8 n-butyllithium 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 14274-07-8 methyl trans-β-benzoylacrylate 
• 1607842-13-6 (R)-methyl 4-phenyl-4-(trimethylsilyloxy)but-2-ynoate 
• 1607842-14-7 (S)-4-allyl-5-phenylfuran-2(5H)-one 
• 1607841-95-1 4-allyl-5-phenylfuran-2(5H)-one 
• 1401693-26-2 3-bromo-4-iodo-5-phenylfuran-2(5H)-one 
• 1401693-17-1 3-chloro-4-iodo-5-phenylfuran-2(5H)-one 

Relevant articles and documents

Synthesis of New γ-Lactams with gem-Difluorinated Side Chains

A short and efficient approach has been designed for the synthesis of new γ-lactams that feature gem-difluorinated side-chains in position 4. The key steps involve 1,4-addition of nitroalkane anions on electrophilic gem-difluoroalkenes, followed by a cascade nitro reduction-heterocyclization. This flexible strategy also allows easy introduction of substituents in positions 3 or 5.

Relative Rates of Metal-Free Azide-Alkyne Cycloadditions: Tunability over 3 Orders of Magnitude

The thermal (3 + 2) dipolar azide-alkyne cycloaddition, proceeding without copper or strained alkynes, is an underutilized ligation with potential applications in materials, bioorganic, and synthetic chemistry. Herein, we investigate the effects of alkyne substitution on the rate of this reaction, both experimentally and computationally. Electron-withdrawing groups accelerate the reaction, providing a range of relative rates from 1.0 to 2100 between the slowest and fastest alkynes studied. Unexpectedly, aryl groups conjugated to the alkyne significantly retard the reaction rate. In contrast, a sulfonyl, ester-substituted alkyne is reactive enough that it couples with an azide at room temperature in a few hours. This reactivity scale should provide a guide to those who wish to use this ligation under mild conditions.

Highly enantioselective catalytic methyl propiolate addition to both aromatic and aliphatic aldehydes

The excellent catalytic effect on methyl propiolate addition to a wide range of aromatic and aliphatic aldehydes promoted by inexpensive and commercially available BINOL-based ligand is reported. The catalyst systems showed high yields and excellent enantioselectivities for aromatic aldehydes, and excellent yields and high enantioselectivities for aliphatic aldehydes.