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A11437
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

 

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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
TSCA: Yes
RTECS: ES0175000