Dimethyl acetylenedicarboxylate
General
Systematic name	Dimethyl acetylenedicarboxylate
Other names	DMAD Acetylenedicarboxylic acid, dimethyl ester
Molecular formula	C6H6O4
SMILES	O=C(OC)C#CC(OC)=O
Molar mass	142.11 g/mol
Appearance	Colorless liquid
CAS number	[762-42-5]
Properties
Density and phase	1.1564 g/cm3
Solubility in water	Insoluble
Other solvents	Soluble in most organic solvents
Melting point	-117 °C
Boiling point	195–198 °C 96–98° at 8 mm Hg
Structure
Dipole moment	0 D
Hazards
MSDS	External MSDS
Main hazards	Toxic gas
NFPA 704
Flash point	187 °F
R/S statement	R: R34 S: S23 S26 S27 S36/37/39 S45
RTECS number	ES0175000
Supplementary data page
Structure and properties	n = 1.447
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related compounds	Methyl propiolate, Hexafluoro-2-butyne, Acetylene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Dimethyl acetylenedicarboxylate (DMAD) is the organic compound with the formula CH₃O₂CC₂CO₂CH₃. This alkyne, which exists as a liquid at room temperature, is highly electrophilic. As such, DMAD, as it is commonly called in the laboratory, is widely employed as a dienophile in cycloaddition reactions, such as the Diels-Alder reaction. It is also a potent Michael acceptor.^[1] IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density, or volumic mass (ISO 31), is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that Solid solubility be merged into this article or section. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... // The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Propiolic acid, or acetylene mono-carboxylic acid, is an unsaturated organic acid prepared by boiling acetylene dicarboxylic acid, obtained by the action of alcoholic potash on dibromosuccinic acid, or its acid potassium salt with water. ... Acetylene (IUPAC name: ethyne) is the simplest alkyne hydrocarbon, consisting of two hydrogen atoms and two carbon atoms connected by a triple bond. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a substance. ... A dienophile can only properly be explained by being familar with a Diels-Alder reaction. ... The Diels-Alder reaction The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. ... The Michael reaction or Michael addition is the nucleophilic addition of an carbanion to an alpha, beta unsaturated carbonyl compound. ...

Preparation

Although inexpensively available, DMAD is prepared today as it was originally.^[2] Maleic acid is brominated and the resulting dibromosuccinic acid is dehydrohalogenated.^[3] The dicarboxylic acid is then esterified with methanol and sulfuric acid as a catalyst.^[4] Maleic acid or (Z)-Butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). ... Halogenation is a chemical reaction that replaces a hydrogen atom with a halogen atom. ... Succinic acid, originally called spirit of amber, is a carboxylic acid with the formula: HOOC-CH2-CH2-COOH At room temperature, pure succinic acid is a solid that forms colorless, odorless prisms. ... Dehydrohalogenation is an organic chemistry reaction from which an alkene is obtained from an alkyl halide. ... Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. ... Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... Methanol, also known as methyl alcohol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ...

Safety

DMAD is a lachrymator and a vesicant. A lachrymatory agent or lachrymator is a chemical compound that irritates the eyes to cause tearing, pain, and even temporary blindness. ... A vesicant (also known as a blister agent) is a chemical agent that causes blistering of the skin. ...

References

1. ^ Stelmach, J. E.; Winkler, J. D. “Dimethyl Acetylenedicarboxylate”in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
2. ^ Bandrowski, E. “Ueber Acetylendicarbonsäure” Chemische Berichte band 10, 838 (1877).
3. ^ Abbott, T. W.; Arnold, R. T.; Thompson, R. B. “Acetylenedicarboxyltic acid” Organic Syntheses, Collective Volume 2, page 10.
4. ^ Huntress, E. H. Lesslie, T. E.; Bornstein, J. “Dimethyl Acetylenedicarboxylate” Organic Syntheses, Collective Volume 4, page 329.

External links

• Links to external chemical sources.