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E46607

Sigma-Aldrich

Ethyl propiolate

99%

Synonym(s):

Ethyl acetylenecarboxylate

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About This Item

Linear Formula:
HC≡CCO2C2H5
CAS Number:
623-47-2
Molecular Weight:
98.10
Beilstein:
878250
EC Number:
210-795-8
MDL number:
MFCD00009184
UNSPSC Code:
12352100
PubChem Substance ID:
24894572
NACRES:
NA.22

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.412 (lit.)

bp

120 °C (lit.)

density

0.968 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C#C

InChI

1S/C5H6O2/c1-3-5(6)7-4-2/h1H,4H2,2H3

InChI key

FMVJYQGSRWVMQV-UHFFFAOYSA-N

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Application

Halogenated derivatives were used as substrates for direct, asymmetric alkynylation of cyclic ß-ketoesters using chiral phase-transfer catalysts. Also employed in a one-pot , four-component synthesis of benzene-1,2,3,5-tetracarboxylates promoted by Ph3P.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000132572
0000132573
STBK2879
0000092778
STBJ7140

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Thomas B Poulsen et al.
Journal of the American Chemical Society, 129(2), 441-449 (2007-01-11)
The first organocatalytic enantioselective direct alpha-alkynylation of beta-ketoesters and 3-acyl oxindoles is described. It is demonstrated that activated beta-halo-alkynes undergo nucleophilic acetylenic substitution catalyzed by chiral phase-transfer compounds to afford the alkynylated products in high yields and excellent enantioselectivities. The
Peter Morrison-Whittle et al.
Frontiers in microbiology, 9, 910-910 (2018-06-06)
The products of microbial metabolism form an integral part of human industry and have been shaped by evolutionary processes, accidentally and deliberately, for thousands of years. In the production of wine, a great many flavor and aroma compounds are produced
Kh Mahid Uddin et al.
Dalton transactions (Cambridge, England : 2003), 46(39), 13597-13609 (2017-09-28)
The reactivity of the face-capped benzothiazolate clusters HOs
Helvetica Chimica Acta, 89, 2918-2918 (2006)
Mikhail V Dobrynin et al.
Carbohydrate polymers, 241, 116327-116327 (2020-06-09)
Hydrosilylation catalyzed by the rhodium(I) complex [Rh(acac)(CO)2] or platinum(0)-based Karstedt's catalyst was employed to combine hydrophilic propargylated hydroxyethyl cellulose and hydrophobic hydride-terminated polydimethylsiloxane to give polymer hybrid structures. The final polymers were characterized by FTIR, solid state 1H, 13C and
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