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543195

Sigma-Aldrich

Methyl phenylpropiolate

97%

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About This Item

Linear Formula:
C6H5C≡CCO2CH3
CAS Number:
Molecular Weight:
160.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

refractive index

n20/D 1.5590 (lit.)

bp

109-112 °C/2 mmHg (lit.)

density

1.086 g/mL at 25 °C (lit.)

functional group

ester
phenyl

SMILES string

COC(=O)C#Cc1ccccc1

InChI

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

InChI key

JFGWPXKGINUNDH-UHFFFAOYSA-N

General description

Organoiron carbonyl complexes are obtained by reacting methyl phenylpropiolate with Fe2(CO)9.

Application

Methyl phenylpropiolate may be used in the synthesis of:
  • bicyclohexadienes
  • cis-methyl cinnamate
  • (E)-alkyl 3-(dialkoxyphosphoryl)-3-phenylacrylate derivatives

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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P Andrew Evans et al.
Journal of the American Chemical Society, 127(36), 12466-12467 (2005-09-08)
Transition metal-catalyzed [m+n+o] carbocyclization reactions provide powerful methods for the construction of complex polycyclic systems that are generally not accessible through classical pericyclic reactions. We have developed the first regio- and enantioselective crossed intermolecular rhodium-catalyzed [2+2+2] carbocyclization of carbon- and
Preparation and Structures of Methyl Phenylpropiolate-Iron Carbonyl Complexes. A New Dicarbonyl-p-cyclopentadienyloxy-s-vinyliron Compound.
Dahl LF, et al.
Journal of the American Chemical Society, 88(3), 446-452 (1966)
The catalyst-free addition of dialkyl phosphites on the triple bond of alkyl phenylpropiolates under microwave conditions.
Balint E, et al.
Current Catalysis, 4(1), 57-64 (2015)
Steric effects on reactivity in silicon chemistry.
Cartledge FK.
Organometallics, 2(3), 425-430 (1983)

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