Dimethyl acetylenedicarboxylate
Dimethyl acetylenedicarboxylate (DMAD), CAS 762-42-5, with the molecular formula C6H6O4 and a molecular weight of 142.11 g/mol, is a highly reactive ester and a valuable building block in organic synthesis. It is particularly recognised for its utility as a versatile dienophile in Diels-Alder cycloaddition reactions, enabling the construction of complex cyclic systems. Available at 99% purity, DMAD is an essential reagent for chemical research and development.
- IUPAC
- Dimethyl 2-butynedioate
- Synonyms
- Dimethyl 2-butynedioateDMAD
Diels-Alder Reactions
DMAD serves as a potent dienophile in Diels-Alder reactions, readily reacting with dienes to form six-membered rings. This cycloaddition is a cornerstone for synthesising complex polycyclic and heterocyclic compounds.
Organic Synthesis Building Block
As a difunctional ester with an activated alkyne, DMAD is a versatile intermediate. It participates in various addition reactions, Michael additions, and cycloadditions, facilitating the synthesis of diverse organic molecules.
Heterocycle Synthesis
The electron-deficient triple bond in DMAD makes it a key reagent for constructing various heterocyclic systems. It reacts with nucleophiles and 1,3-dipoles to form pyrroles, pyridines, and other nitrogen-containing heterocycles.
| Molecular weight | 142.11 |
|---|---|
| Linear formula | CH3OCOC≡CCO2CH3 |
| Assay | 99% |
| Boiling point | 95-98 °C/19 mmHg(lit.) |
| Density | 1.156 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.447(lit.) |
| Application | Versatile dienophile used in Diels-Alder reactions.1,2,3 |
Hazard statements
- H302Harmful if swallowed
- H314Causes severe skin burns and eye damage
Precautionary statements
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
- P310Immediately call a POISON CENTER or doctor
| Protective equipment | Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 86 °C / 186.8 °F |
| Transport (UN / ADR) | UN 3265 8 / PGII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | C |
| Risk statements (R) | 34 |
| Safety statements (S) | 23-26-27-36/37/39-45 |
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 Dimethyl acetylenedicarboxylate (DMAD) primarily used for?
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DMAD (CAS 762-42-5) is primarily used as a versatile dienophile in Diels-Alder reactions and as a general building block in organic synthesis for constructing complex molecules and heterocycles.
What is the CAS number and molecular formula for Dimethyl acetylenedicarboxylate?
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The CAS number for Dimethyl acetylenedicarboxylate is 762-42-5, and its linear formula is CH3O2C-C≡C-CO2CH3 (C6H6O4).
What grade and purity does Tech Serve Solutions supply for Dimethyl acetylenedicarboxylate?
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Tech Serve Solutions supplies Dimethyl acetylenedicarboxylate with a purity of 99%. This product is typically supplied for research and chemical synthesis purposes and is not represented as USP, BP, EP, or any other pharmacopoeia grade.
How should Dimethyl acetylenedicarboxylate be handled safely?
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Dimethyl acetylenedicarboxylate is a hazardous substance (GHS05, GHS07, Danger). It is harmful if swallowed (H302) and causes severe skin burns and eye damage (H314). Handle with appropriate personal protective equipment, including full-face respirators, chemical-resistant gloves, and eye protection. Work in a well-ventilated area or fume hood.
Is Dimethyl acetylenedicarboxylate a controlled substance?
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The provided data does not indicate that Dimethyl acetylenedicarboxylate is a controlled substance.
How is Dimethyl acetylenedicarboxylate packed, shipped, and exported?
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Tech Serve Solutions packs, ships, and exports chemicals adhering to all relevant safety and regulatory standards for hazardous materials. Specific packaging details are available upon request.
How can I request a sample or a quote for Dimethyl acetylenedicarboxylate?
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To request a sample or a quote for Dimethyl acetylenedicarboxylate, please contact our sales department through the website or by phone, providing your specific requirements.
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