4891-38-7

Basic information

• Product Name: METHYL PHENYLPROPIOLATE
• Synonyms: METHYL-(PHENYLPROPIOLAT);METHYL PHENYLPROPIOLATE;METHYL 3-PHENYLPROPIOLATE;PHENYLPROPIOLIC ACID METHYL ESTER;2-Phenyl-1-carbomethoxyacetylene;2-Propynoic acid, 3-phenyl-, methyl ester;Methyl 3-phenyl-2-propynoate;Methyl 3-phenylpropynoate
• CAS NO: 4891-38-7
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• Product Categories: C10 to C11;Carbonyl Compounds;Esters
• Mol File: 4891-38-7.mol
• Article Data: 103

Chemical Properties

• Melting Point: 26°C
• Boiling Point: 109-112 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow/Liquid After Melting
• Density: 1.086 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.025mmHg at 25°C
• Refractive Index: n20/D 1.5590(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 472813
• CAS DataBase Reference: METHYL PHENYLPROPIOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL PHENYLPROPIOLATE(4891-38-7)
• EPA Substance Registry System: METHYL PHENYLPROPIOLATE(4891-38-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4891-38-7(Hazardous Substances Data)

Usage

Description

METHYL PHENYLPROPIOLATE, also known as Methyl Phenyl Propiolate, is an organic compound with the chemical formula C10H10O2. It is a clear colorless to pale yellow liquid and is known for its reactivity in various chemical reactions, particularly in the synthesis of different organic compounds.

Uses

Used in Chemical Synthesis:
METHYL PHENYLPROPIOLATE is used as a key intermediate for the synthesis of various organic compounds, such as bicyclohexadienes, cis-methyl cinnamate, and (E)-alkyl 3-(dialkoxyphosphoryl)-3-phenylacrylate derivatives. Its reactivity and versatility make it a valuable component in the development of new chemical products.
Used in Organoiron Carbonyl Complexes:
METHYL PHENYLPROPIOLATE is used as a reactant in the formation of organoiron carbonyl complexes when combined with Fe2(CO)9. These complexes have potential applications in various fields, including catalysis and materials science.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 4859, 1987 DOI: 10.1021/jo00231a007Tetrahedron Letters, 21, p. 849, 1980 DOI: 10.1016/S0040-4039(00)71522-X

InChI:InChI=1/C10H8O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-6H,1H3

Upstream product

• 67-56-1 methanol 
• 27412-71-1 5-phenyl-1H-pyrazol-3(2H)-one 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 108-86-1 bromobenzene 
• 922-67-8 propynoic acid methyl ester 
• 405-42-5 2',2'-difluorostyrene 
• 107-06-2 1,2-dichloro-ethane 
• 637-44-5 phenylpropyolic acid 
• 3375-31-3 palladium diacetate 
• 13894-21-8 ethynyl p-tolyl sulfone 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 7063-23-2 phenylpropiolic acid sodium salt 

Downstream Products

• 50561-87-0 4,5-diphenyl-1⁽²⁾H-pyrazole-3-carboxylic acid methyl ester 
• 24161-43-1 methyl 3-phenylbicyclo<2.2.1>hepta-2,5-diene-2-carboxylate 
• 41126-46-9 3-methyl-4-phenyl-2-thioxo-2,3-dihydro-thiazole-5-carboxylic acid methyl ester 
• 3837-78-3 2-Cyan-6-methyl-7-<(1-phenyl-2-methoxycarbonyl-vinyl)-amino>-hepta-2,4,6-trien-saeure-methylester 
• 90900-33-7 methyl 3a,4,5,6-tetrahydro-3a,6,6-trimethyl-2-phenyl-pyrrolo<1,2-b>isoxazole-3-carboxylate 
• 111557-81-4 4-Methyl-2-phenyl-pyrrolo[1,2-a]quinoxaline-1-carboxylic acid methyl ester 
• 79230-01-6 (Z)-methyl 3-phenyl-3-(p-tolylamino)acrylate 
• 108286-45-9 3-Methyl-2-phenyl-6,7-dihydro-5H-pyrrolizine-1-carboxylic acid methyl ester 
• 108286-44-8 3-Methyl-1-phenyl-6,7-dihydro-5H-pyrrolizine-2-carboxylic acid methyl ester 
• 25359-49-3 Methyl 4-oxo-3-phenylpentanoate 
• 70218-14-3 Z-4-Acetoxy-3-phenyl-3-penten-saeure-methylester 
• 70218-15-4 E-4-Acetoxy-3-phenyl-3-penten-saeure-methylester 
• 70461-40-4 1-(2-Hydroxy-cyclopent-1-enyl)-3-phenyl-propynone 
• 168893-90-1 3-Amino-5-(2-phenylethynyl)-1H-1,2,4-triazole 

Relevant articles and documents

SF5-Enolates in Ti(IV)-Mediated Aldol Reactions

The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF5-acetates with aldehydes in the presence of TiCl4 in the non-nucleophilic solvent CH2Cl2

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Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.55.0 equiv) in toluene at 6080 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.