Methoxyallene
Methoxyallene (CAS: 13169-00-1, C4H6O, MW: 70.09) is a valuable organic building block and reactant in diverse chemical syntheses. This allene derivative is known for its utility in multicomponent reactions, hydroamination, and cyclization processes, leading to complex heterocyclic compounds and carbocycles. Methoxyallene serves as a versatile starting material for creating substituted pyrroles, dihydropyridines, and various functionalised molecules, making it a key intermediate for organic synthesis.
- IUPAC
- 1-Methoxy-1,2-propadiene,Methyl propadienyl ether,NSC 363923
Synthesis of Enantiopure Pyridines
Methoxyallene is employed as a reactant in multicomponent reactions with nitriles and carboxylic acids, followed by cyclocondensation. This pathway facilitates the synthesis of enantiopure pyridine derivatives.
Intermolecular Hydroamination
This compound participates in intermolecular hydroamination reactions. This process allows for the addition of N-H bonds across the unsaturated system of methoxyallene.
Pyrrole and Dihydropyridine Synthesis
It is used in one-pot synthesis methods for preparing alkoxy and (alkylsulfanyl)-substituted pyrroles and dihydropyridines, offering efficient routes to these heterocycles.
Cycloaddition Reactions
Methoxyallene can undergo intermolecular [4+2] cycloaddition reactions with dienes. This enables the formation of cyclic structures through the reaction of the allene with conjugated dienes.
Allenyl Cyclization and Transformations
The compound is involved in allenyl cyclization reactions, which can be subsequently transformed into dicarbonyl compounds, cyclopentenones, and butenolide structures.
| Molecular weight | 70.09 |
|---|---|
| Empirical formula | C4H6O |
| Grade | technical grade |
| Density | 0.832 g/mL at 25 °C |
| Refractive index | n20/D 1.429 |
| Storage temperature | 2-8°C |
| Application | Reactant involved in:• Multicomponent reactions with nitriles and carboxylic acids followed by cyclocondensation for synthesis of enantiopure pyridines1• Intermolecular hydroamination2• One-pot synthesis of alkoxy and (alkylsulfanyl)-substituted pyrroles and dihydropyridines3• Intermolecular [4+2] cycloaddition with dienes4• Allenyl cyclization and subsequent transformation into dicarbonyl, cyclopentenones, and butenolide compounds5• Insertion reactions of C-C pi-bonds into alkylidenesilacyclopropanes6 |
Hazard statements
- H225Highly flammable liquid and vapour
Precautionary statements
- P210Keep away from heat, sparks and open flames. No smoking
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US) |
|---|---|
| Flash point | -28 °C / -18.4 °F |
| Transport (UN / ADR) | UN 1993BE 3 / PGII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | F |
| Risk statements (R) | 11 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Methoxyallene used for?
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Methoxyallene is primarily used as a reactant in organic synthesis. It is involved in reactions such as multicomponent reactions for pyridine synthesis, intermolecular hydroamination, and the one-pot synthesis of substituted pyrroles and dihydropyridines, as well as cycloaddition and cyclization reactions.
What are the CAS number and formula for Methoxyallene?
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The CAS number for Methoxyallene is 13169-00-1, and its empirical formula is C4H6O.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Methoxyallene in technical grade. We do not represent this product as USP, BP, or EP grade.
How should Methoxyallene be handled safely?
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Methoxyallene is highly flammable (H225) and requires careful handling. It should be stored at 2-8°C and used with appropriate personal protective equipment, including eyeshields, gloves, and a suitable respirator, in a well-ventilated area away from ignition sources.
Is Methoxyallene a controlled substance?
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The provided data does not indicate that Methoxyallene is a controlled substance.
How is Methoxyallene packed and shipped?
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Methoxyallene is shipped as UN 1993, Class 3, Packing Group II, indicating it is a flammable liquid. Specific packing configurations are available upon request.
How can I request a quote or sample for Methoxyallene?
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To request a quote or sample for Methoxyallene, please contact our sales department through the TSS website or your designated account manager.
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