Methyl propiolate (HCID 13536)

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 properties

XLogP: 0.6
Topological polar surface area: 26.3 Å²
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
Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents, bases, acids.
InChI: 1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3
InChIKey: IMAKHNTVDGLIRY-UHFFFAOYSA-N
SMILES: COC(=O)C#C
CAS DataBase Reference: 922 · 922-67-8(CAS DataBase Reference)
FDA UNII: 88 NXO102K · T88NXO102K
NIST Chemistry Reference: 2 · 2-Propynoic acid, methyl ester(922-67-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger
Hazard statements: 225 · H225-H315-H319-H335
Precautionary statements: 210 · P210-P233-P240-P241-P303+P361+P353-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: F,Xi
Risk Statements: 11 · 11-36/37/38-36
Safety Statements: 26 · 26-36-36/37/39-23-16-33-7/9
RIDADR: 3272 · UN 3272 3/PG 2
WGK Germany: 3 · 3
RTECS: 50000 · UE0050000
F: 19 · 19
Hazard Note: Highly Flammable/Harmful
HazardClass: 3 · 3
PackingGroup: II
HS Code: 29161980 · 29161980
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Flam · Eye Irrit. 2Flam. Liq. 2Skin 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 · 4 items

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
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: II
target organs: Respiratory system
Hazard statements: H225-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. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P210-P233-P240-P241-P303+P361+P353-P305+P351+P338

Chemistry & industry

Applications · 2 items

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.