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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

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.)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)

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