Basic information
- CAS
623-47-2- Standard SMILES
C#CC(=O)OCC- InChIKey
FMVJYQGSRWVMQV-UHFFFAOYSA-N- Molecular formula
- C5H6O2
- Average molar mass
- 98.1 g/mol
- Monoisotopic mass
- 98.03677943
Overview
Ethyl propiolate is the ethyl ester of prop-2-ynoic acid. It is an ethyl ester, a ynoate ester and a terminal acetylenic compound.
Names & identifiers
- Preferred name
- Ethyl propiolate
- IUPAC
- ethyl prop-2-ynoate
- English name
- Ethyl propiolate
- Molecular formula
- C5H6O2
- Molecular weight
- 98.1
Names & synonyms
Ethyl propiolate623-47-2ethyl prop-2-ynoateEthyl acetylenecarboxylateETHYL PROPYNOATE(Ethoxycarbonyl)acetyleneNSC-60551W235G5U52SCHEBI:51740DTXSID80211359RefChem:596387DTXCID30133850
Show more names
EPLPropioLHC≡CCO2C2H5Ethyl propinateEthylPropiolate>
210-795-82-Propynoic acid, ethyl esterEthyl 2-propynoatePropiolic acid ethyl esterethyl propargylatePropargylic Acid Ethyl EsterPropiolic acid, ethyl esterMFCD00009184
Database identifiers
- CAS
623-47-2- PubChem CID
- 12182
- DTXSID
DTXSID80211359- ChEMBL
CHEMBL53384- ChEBI
CHEBI:51740- UNII
- W235G5U52S
- EC Number
- 210-795-8
- Nikkaji
- J137.953D
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 106
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
SpringerMaterials PropertiesOptical coefficient
Physical DescriptionColorless liquid with a pungent odor; mp = 9 deg C; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 9 °C · 9°C
- Boiling point
- 120 °C · 120 °C (lit.)
- Density
- 0.968 g/mL · 0.968 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.412(lit.)
- Flash point
- 74 °F · 74 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Miscible with alcohol.
- form
- Liquid
- Specific Gravity
- 0.968 · 0.968
- color
- Clear colorless to pale yellow
- Water Solubility
- miscible
- Merck
- 14 · 14,3846
- BRN
- 878250 · 878250
- Dielectric constant
- 7 · 7.0
- InChI
- 1S/C5H6O2/c1-3-5(6)7-4-2/h1H,4H2,2H3
- InChIKey
- FMVJYQGSRWVMQV-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C#C
- CAS DataBase Reference
- 623 · 623-47-2(CAS DataBase Reference)
- FDA UNII
- 235 G5U52S · W235G5U52S
- NIST Chemistry Reference
- Ethyl propiolate(623-47-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 226 · H226-H315-H319-H335
- Precautionary statements
- 210 · P210-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi,F
- Risk Statements
- 10 · 10-36/37/38-36-11
- Safety Statements
- 26 · 26-36-37/39-16-33-29-24-23
- RIDADR
- 3272 · UN 3272 3/PG 3
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29161980 · 29161980
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 Flam · Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Warning
H226 (98.1%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 53 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propynoic acid, ethyl ester
Status: Active Update: 06-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28015
Ethyl acetylenecarboxylate: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin, respiratory tract, and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesFlam. Liq. 3 (98.1%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 3272 3/PG 3
- hs_code
- 29161980
- risk_code
- 10-36/37/38-36-11
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xi,F
- hazard_note
- Irritant
- safety_code
- 26-36-37/39-16-33-29-24-23
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H226-H315-H319-H335
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- Precautionary statements
- P210-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesUsed in organic synthesis and as a peptide coupling reagent; [Merck Index]
Applications
UsesEthyl propiolate is used as a precursor in the preparation of substituted anthraquinones and pyrazolo[1,5-a]pyridine, which exhibits anti-inflammatory activity. Further, it is employed in the synthesis of benzene-1,2,3,5-tetracarboxylates promoted by triphenylphosphine. Its halogenated derivatives are used as a substrate for direct, asymmetric alkynylation of cyclic beta-ketoesters using chiral phase-transfer catalysts.
UsesIn organic synthesis; peptide coupling reagent.
UsesHalogenated derivatives were used as substrates for direct, asymmetric alkynylation of cyclic -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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Ethyl propiolate is the ethyl ester of prop-2-ynoic acid. It is a ynoate ester, a terminal acetylenic compound and an ethyl ester.
Related reactions
710 records
Compound notes
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