Substance
ID:714926
Names and Identifiers
IUPAC name
1,4-dimethyl but-2-ynedioate
IUPAC Traditional name
1,4-dimethyl but-2-ynedioate
Synonyms
Dimethyl acetylenedicarboxylate丁炔二酸二甲酯Butynedioic acid dimethyl esterAcetylenedicarboxylic acid dimethyl ester
Registration numbers
MDL Number
CAS Number
Beilstein Number
EC Number
Properties
Product Information
Purity
98%
Safety Information
GHS Pictograms
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
European Hazard Symbols
Harmful (X)
Corrosive (C)TSCA Listed
是
Hazard Class
8
UN Number
UN1760
Risk Statements
21/22-34
RTECS
ES0175000
GHS Hazard statements
H314-H318-H302-H227
Safety Statements
26-36/37/39-45
Storage Warning
Light Sensitive
Packing Group
II
GHS Precautionary statements
P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A
Physical Property
Boiling Point
195-198°C
Density
1.156
Flash Point
86°C(186°F)
Melting Point
-18°C
Refractive Index
1.4480
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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):
• 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).
• 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):
• 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).
• 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.