Methyl propiolate
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Basic information
- CAS
922-67-8- Standard SMILES
C#CC(=O)OC- InChIKey
IMAKHNTVDGLIRY-UHFFFAOYSA-N- Molecular formula
- C4H4O2
- Average molar mass
- 84.07 g/mol
- Monoisotopic mass
- 84.02112937
Names & identifiers
- Preferred name
- Methyl propiolate
- IUPAC
- methyl prop-2-ynoate
- English name
- Methyl propiolate
- Molecular formula
- C4H4O2
- Molecular weight
- 84.07
Names & synonyms
METHYL PROPIOLATEMethyl propynoatePropiolic acid, methyl estermethyl propargylatePropynoic acid methyl estermethyl 2-propynoateAI3-37828EINECS 213-083-5BRN 0605462T88NXO102KNSC-1541644-02-00-01688 (Beilstein Handbook Reference)
Show more names
4-Methoxy-4-oxobut-2-ynoic acidPROPYNOIC ACID, METHYL ESTERHCequivCCOOCH3Methyl propinoateMETHYPROPIOLATE,99%MethylPropiolate>Sucrose Impurity 14
UNII-T88NXO102Kmethyl acetylenemonocarboxylate(CARBOMETHOXY)ACETYLENE(METHOXYCARBONYL)ACETYLENEDTXSID60238923RefChem:158010DTXCID101614147515-15-3
Database identifiers
- CAS
922-67-8- PubChem CID
- 13536
- DTXSID
DTXSID60238923- ChEMBL
CHEMBL4086262- UNII
- T88NXO102K
- EC Number
- 213-083-5
- Nikkaji
- J87.385C
Properties
Computed structural propertiesFilling in
- XLogP
- 0.6
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 95.4
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Physicochemical properties
- Melting point
- 171 · 171-173 °C
- Boiling point
- 103 · 103-105 °C (lit.)
- Density
- 0.945 g/mL · 0.945 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.408(lit.)
- Flash point
- 50 °F · 50 °F
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Chloroform (Sparingly), Methanol (Sparingly)
- form
- Liquid
- Specific Gravity
- 0.945 · 0.9450
- color
- Clear colorless
- Water Solubility
- Not miscible in water.
- BRN
- 605462 · 605462
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger 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 69 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 12-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24695
Hazard Classes and CategoriesFlam. Liq. 2 (100%)
Safety data
- F
- 19
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- UE0050000
- ridadr
- UN 3272 3/PG 2
- hs_code
- 29161980
- risk_code
- 11-36/37/38-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- hazard_note
- Highly Flammable/Harmful
- safety_code
- 26-36-36/37/39-23-16-33-7/9
Chemistry & industry
Applications
UsesMethyl propiolate was used in the synthesis of polysubstituted 3-arylaminoacrylate and tetrahydropyrimidin-2-one derivatives. It was also used as a thiol derivatizing agent for capillary electrophoresis.
General DescriptionMethyl Propiolate is an α,β-unsaturated ester that can undergo Diels-Alder and various other cycloaddition reactions, Michael additions, acetylide formation, halogen addition, as well as a range of cyclization reactions to produce heterocycles and aromatic compounds.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
497 records
Compound notes
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