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Dimethyl acetylenedicarboxylate information


Dimethyl acetylenedicarboxylate
Chemical structure of DMADuak
Ball-and-stick model
Names
Preferred IUPAC name
Dimethyl but-2-ynedioate
Other names
DMAD
Acetylenedicarboxylic
acid dimethyl ester
Identifiers
CAS Number
  • 762-42-5 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL3248452
ChemSpider
  • 12440 checkY
ECHA InfoCard 100.010.999 Edit this at Wikidata
EC Number
  • 212-098-4
PubChem CID
  • 12980
RTECS number
  • ES0175000
UNII
  • 7HZA2PL15F
CompTox Dashboard (EPA)
  • DTXSID0061088 Edit this at Wikidata
InChI
  • InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 checkY
    Key: VHILMKFSCRWWIJ-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
    Key: VHILMKFSCRWWIJ-UHFFFAOYAX
SMILES
  • COC(=O)C#CC(=O)OC
Properties
Chemical formula
C6H6O4
Molar mass 142.11 g/mol
Appearance Colorless liquid
Density 1.1564 g/cm3
Melting point −18 °C (0 °F; 255 K)
Boiling point 195 to 198 °C (383 to 388 °F; 468 to 471 K) (96–98° at 8 mm Hg)
Solubility in water
Insoluble
Solubility in other solvents Soluble in most
organic solvents
Refractive index (nD)
1.447
Structure
Dipole moment
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
GHS labelling:
Pictograms
GHS05: CorrosiveGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H302, H314
Precautionary statements
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Flash point 187 °C (369 °F; 460 K)
Related compounds
Related compounds
Methyl propiolate,
Hexafluoro-2-butyne,
Acetylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethyl acetylenedicarboxylate (DMAD) is an organic compound with the formula CH3O2CC2CO2CH3. It is a di-ester in which the ester groups are conjugated with a C-C triple bond. As such, the molecule is highly electrophilic, and is widely employed as a dienophile in cycloaddition reactions, such as the Diels-Alder reaction. It is also a potent Michael acceptor.[1][2] This compound exists as a colorless liquid at room temperature. This compound was used in the preparation of nedocromil.

  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:10.1002/047084289X.
  2. ^ Sahoo, Manoj (2007). "Dimethyl Acetylene Dicarboxylate". Synlett. 2007 (13): 2142–2143. doi:10.1055/s-2007-984894.

and 18 Related for: Dimethyl acetylenedicarboxylate information

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Dimethyl acetylenedicarboxylate

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Dimethyl acetylenedicarboxylate (DMAD) is an organic compound with the formula CH3O2CC2CO2CH3. It is a di-ester in which the ester groups are conjugated...

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Thiazole

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a very mild reaction of a 2-(dimethylamino)thiazole with dimethyl acetylenedicarboxylate (DMAD) to a pyridine was found to proceed through a zwitterionic...

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Acetylenedicarboxylic acid

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acid. Acetylenedicarboxylic acid is used in the synthesis of dimethyl acetylenedicarboxylate, an important laboratory reagent. The acid is commonly traded...

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Indole

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Diels–Reese reaction dimethyl acetylenedicarboxylate reacts with 1,2-diphenylhydrazine to an adduct, which in xylene gives dimethyl indole-2,3-dicarboxylate...

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Dodecahedrane

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materials cyclopentadiene (2 equivalents 10 carbon atoms), dimethyl acetylenedicarboxylate (4 carbon atoms) and allyltrimethylsilane (2 equivalents, 6...

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Coniine

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is of special interest. The initial adduct of pyridine and dimethyl acetylenedicarboxylate is tetramethylquinolizine-1,2,3,4-tetracarboxylate, which on...

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C6H6O4

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mass : 142.10 g/mol, exact mass : 142.026608 u) may refer to: Dimethyl acetylenedicarboxylate 5-Hydroxymaltol 2-Hydroxymuconate semialdehyde Kojic acid Muconic...

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Cyclopropene

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yield by thermolysis of the adduct of cycloheptatriene and dimethyl acetylenedicarboxylate. Allyl chloride undergoes dehydrohalogenation upon treatment...

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Cyclooctatetraene

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give a [4.2.0]-bicyclic compound, which reacts further with dimethyl acetylenedicarboxylate in a Diels-Alder reaction (DA). Retro-DA at 200 °C releases...

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Raltegravir

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of the drug is then created when the amidoxime reacts with dimethyl acetylenedicarboxylate. The synthesis is completed by conversion of the remaining...

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Thermodynamic versus kinetic reaction control

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reaction of bis-furyl dienes 3 with hexafluoro-2-butyne or dimethyl acetylenedicarboxylate (DMAD) have been discovered and described in 2018. At low temperature...

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Cyclophane

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Dewar benzene derivative. Heat reverses the reaction. With dimethyl acetylenedicarboxylate, [6]metacyclophane rapidly undergoes the Diels-Alder reaction...

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Diphenylacetylene

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Scientific MSDS Related compounds Related compounds But-2-yne Dimethyl acetylenedicarboxylate Except where otherwise noted, data are given for materials...

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Bismuthinidene

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heterocyclic diene in the presence of the electron-deficient alkyne dimethyl acetylenedicarboxylate (DMAD), performing a hetero Diels-Alder [4+2] cycloaddition...

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Metal dithiolene complex

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method entail the reaction of electrophilic acetylenes such as dimethyl acetylenedicarboxylate with well defined polysulfido complexes. Early studies on dithiolene...

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Stetter reaction

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under Stetter conditions for coupling aromatic aldehydes with dimethyl acetylenedicarboxylate (DMAD), whereby the thiazolium ylide is hydrolyzed by the aromatization...

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Diethyl azodicarboxylate

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March 2011. DEAD is sometimes used for another chemical, diethyl acetylenedicarboxylate. P. N. Preston (1980). Benzimidazoles and congeneric tricyclic compounds...

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Oxocarbon anion

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Thus, for example, the oxalate moiety [−O−(C=O)2−O−] occurs in the ester dimethyl oxalate H3C−O−(C=O)2−O−CH3. The carbonate ion has a trigonal planar structure...

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