Dimethyl acetylenedicarboxylate

• Catalog No.: A11437
• CAS Number: 762-42-5
• M. F.: C6H6O4
• M. W.: 142.10944
• Purity: 98%

SYNONYMS

• Title: 丁炔二酸二甲酯
• IUPAC name: 1,4-dimethyl but-2-ynedioate
• IUPAC Traditional name: 1,4-dimethyl but-2-ynedioate
• Synonyms: Acetylenedicarboxylic acid dimethyl ester; Butynedioic acid dimethyl ester

DATABASE IDS

• MDL Number: MFCD00008456
• EC Number: 212-098-4
• CAS Number: 762-42-5
• Beilstein Number: 607063

PROPERTIES

• Purity: 98%
• Boiling Point: 195-198°C
• Density: 1.156
• Flash Point: 86°C(186°F)
• Melting Point: -18°C
• Refractive Index: 1.4480
• GHS Hazard statements: H314-H318-H302-H227
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 21/22-34
• RTECS: ES0175000
• Safety Statements: 26-36/37/39-45
• Storage Warning: Light Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN1760
• Packing Group: II

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 ?-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.