CAS Number: 23326-27-4
Chemical Name: Methyl but-2-ynoate
IUPAC Name: Methyl but-2-ynoate
Synonyms:
Methyl 2-butynoate;
2-Butynoic acid methyl ester;
Methyl tetrolate;
Crotonic acid methyl ester (alkyne form)
Molecular Formula: C₅H₆O₂
Molecular Weight: ~98.10 g/mol
Appearance: Colorless to pale yellow liquid
Physical State: Liquid
Melting Point: Approximately -70 to -75 °C
Boiling Point: Typically 100–105 °C (at atmospheric pressure; may vary slightly depending on purity)
Density: ~0.95–1.00 g/cm³
Solubility:
Soluble in most organic solvents such as ethanol, ether, acetone, and chloroform; limited solubility in water
Stability:
Stable under normal laboratory conditions; may polymerize or decompose under strong acidic or basic conditions; sensitive to strong oxidizing agents
Functional Groups:
Ester group (–COOCH₃)
Terminal alkyne functionality (–C≡C–)
Conjugated carbonyl system
Chemical Class:
Alkyne ester / Acetylenic ester / Unsaturated ester
SMILES (representative):
CC#CC(=O)OC
InChI Key (representative):
(Varies by database; available from chemical registries)
23326-27-4 (Methyl but-2-ynoate) is widely used as a reactive building block in organic synthesis due to its activated alkyne and ester functionalities.
It is particularly useful in:
Carbon–carbon bond formation reactions
Cycloaddition reactions (e.g., Diels–Alder and [2+2] reactions)
Nucleophilic addition reactions
Transition-metal-catalyzed coupling reactions
The conjugated alkyne–ester structure enhances electrophilicity, making it a versatile intermediate.
Used in:
Synthesis of pharmaceutical intermediates
Preparation of heterocyclic compounds
Manufacture of specialty chemicals
Development of agrochemical intermediates
Its compact structure allows incorporation into more complex molecular frameworks.
Commonly employed in:
Academic organic chemistry laboratories
Medicinal chemistry programs
Development of novel synthetic methodologies
Studies involving alkyne reactivity and ester transformations
The combination of an alkyne and ester group makes it highly suitable for multi-step synthetic routes.
GHS Classification (typical for similar compounds):
Flammable liquid
Harmful if swallowed
Causes skin and eye irritation
May cause respiratory irritation
Common Hazard Statements:
H226: Flammable liquid and vapor
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Precautionary Statements:
P210: Keep away from heat/sparks/open flames
P261: Avoid breathing vapors
P280: Wear protective gloves and eye protection
P305 + P351 + P338: IF IN EYES, rinse cautiously with water
P301 + P312: IF SWALLOWED, call a doctor if you feel unwell
Handle in a well-ventilated area using appropriate personal protective equipment (PPE).
Typical Purity: 95–99% (Research and Industrial Grade)
Storage Conditions:
Store in a tightly sealed container
Keep in a cool, dry, and well-ventilated area
Protect from heat, moisture, and direct sunlight
Keep away from strong oxidizing agents and bases
Commercial Use:
Available from specialty chemical manufacturers for research and industrial organic synthesis applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.
23326-27-4 (Methyl but-2-ynoate) is an important acetylenic ester widely utilized as a reactive intermediate in organic synthesis. Its alkyne and ester functionalities enable diverse transformations including carbon–carbon bond formation, cycloaddition reactions, and pharmaceutical intermediate development, making it a valuable compound in fine chemical and research applications.
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