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A11437 762-42-5 Dimethyl acetylenedicarboxylate, 98% Acetylenedicarboxylic acid dimethyl ester Butynedioic acid dimethyl ester Alfa Aesar


Certificate of Analysis

Dimethyl acetylenedicarboxylate, 98%

CAS: 762-42-5 MDL: MFCD00008456  EINECS: 212-098-4
UN#:UN1760Hazard Class:8Packing Group:II
Alternate Name: Acetylenedicarboxylic acid dimethyl ester
Butynedioic acid dimethyl ester


Pricing and Availability

Size ($) Price Your Price Quantity Options Availability
25g 68.80 Check Availability Add to Favorites Enter qty and click checkbox
100g 237.00 Check Availability Add to Favorites Enter qty and click checkbox
500g 945.00 Check Availability Add to Favorites Enter qty and click checkbox

Chemical Properties

Formula: C6H6O4  Flash point: 86°(186°F)
Formula weight: 142.11  Density: 1.156
Melting point: -18° Refractive Index: 1.4525
Boiling point: 95-98°/19mm Sensitivity: Light Sensitive

Literature References

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.

Other References

Beilstein: 607063
UN#: UN1760
Harmonized Tariff Code: 2917.19

GHS Hazard and Precautionary Statements

Hazard Statements : H314-H318-H302-H227

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed. Combustible liquid.

Precautionary Statements : P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A

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.

CorrosiveHarmful or Irritant

Risk & Safety

Risk Phrases: 22-34
Harmful if swallowed. Causes burns.
Safety Phrases: 20-23-26-36/37/39-45-60
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.
Harmful Corrosive
RTECS: ES0175000