Dimethyl acetylenedicarboxylate, 98%
|UN#:||UN1760||Hazard Class:||8||Packing Group:||II|
|Alternate Name:||Acetylenedicarboxylic acid dimethyl ester
Butynedioic acid dimethyl ester
Pricing and Availability
|Size||($) Price||Your Price||Quantity||Options||Availability|
|Melting point:||-18°||Refractive Index:||1.4525|
|Boiling point:||95-98°/19mm||Sensitivity:||Light Sensitive|
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).
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).
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):
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):
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.
|Harmonized Tariff Code:||2917.19|
GHS Hazard and Precautionary Statements
Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed. Combustible liquid.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.
Risk & Safety
|Harmful if swallowed. Causes burns.|
|When using do not eat or drink. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). This material and/or its container must be disposed of as hazardous waste.|