Dimethyl acetylenedicarboxylate, 98%, Thermo Scientific Chemicals
Dimethyl acetylenedicarboxylate, 98%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

Dimethyl acetylenedicarboxylate, 98%, Thermo Scientific Chemicals

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500 g
25 g
100 g
Catalog number A11437.36
also known as A11437-36
Price (USD)/ Each
1,212.00
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Quantity:
500 g
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Price (USD)/ Each
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Dimethyl acetylenedicarboxylate, 98%, Thermo Scientific Chemicals
Catalog numberA11437.36
Price (USD)/ Each
1,212.00
-
Add to cart
Chemical Identifiers
CAS762-42-5
IUPAC Name1,4-dimethyl but-2-ynedioate
Molecular FormulaC6H6O4
InChI KeyVHILMKFSCRWWIJ-UHFFFAOYSA-N
SMILESCOC(=O)C#CC(=O)OC
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)Clear colorless to yellow
FormLiquid
Assay (GC)≥97.5%
Identification (FTIR)Conforms
Refractive Index1.4460-1.4500 @ 20?C
It acts as an inhibitor of oxidative phosphorylation. It is also used in Pharmaceutical and electronic industry. It is used in organic synthesis. It also acts as an intermediate in chemical research. It is also used in Diels-Alder Reaction.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
It acts as an inhibitor of oxidative phosphorylation. It is also used in Pharmaceutical and electronic industry. It is used in organic synthesis. It also acts as an intermediate in chemical research. It is also used in Diels-Alder Reaction.

Solubility
It is insoluble in water but soluble in ethanol, ethyl ether, CCl4, miscible with organic solvents.

Notes
Stable under normal conditions. Incompatabile to strong oxidizing agents, strong acids, strong bases, Strong reducing agents. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
RUO – Research Use Only

General References:

  1. Peter M. Blonsky.; D. F.Shriver.; Paul Austin.;  H. R. Allcock. Polyphosphazene solid electrolytes. J. Am. Chem. Soc.1984106, (22), 6854-6855.
  2. Barry M. Trost.; Gerald J. Tanoury. An unusual mechanism of a palladium-catalyzed intramolecular carbametalation. A novel palladium-catalyzed rearrangement. J. Am. Chem. Soc.1988110, (5), 1636-1638.
  3. Dienophile in Diels-Alder and related reactions. For addition to a bis-allene, followed by dimerization to a paracyclophane, see: Org. Synth. Coll., 7, 485 (1990).
  4. For use in the masking of double bonds for subsequent release by cycloreversion, see: J. Org. Chem., 44, 962 (1979). Review of cycloreversion reactions in organic synthesis: Synthesis, 121 (1985).
  5. Used in synthesis of a wide variety of heterocyclic systems including benzo[b]thiophenes from thiophenols: Acta Chem. Scand., 27, 595 (1973), and chromones from phenols: Austral. J. Chem., 48, 677 (1995):
  6. Stabilized anions derived from cyclic ß-keto phosphonates undergo ring expansion, via a tandem Michael-Aldol-fragmentation mechanism, to give phosphonates with an additional two carbons in the ring, thus providing a route to highly functionalized medium ring compounds: J. Org. Chem., 60, 3084 (1995):
  7. Reacts with activated carbonyl compounds, such as ɑ-keto esters or ɑ-keto nitriles, in the presence of triphenylphosphine, to give highly functionalized -butyrolactones: J. Org. Chem., 61, 4516 (1996). For a further example with reaction scheme, see 2,2,2-Trifluoroacetophenone, A11403.