1,4-dimethyl but-2-ynedioate

• ChemBase ID: 78495
• Molecular Formular: C6H6O4
• Molecular Mass: 142.10944
• Monoisotopic Mass: 142.02660867
• SMILES: O(C(=O)C#CC(=O)OC)C
• Canonical SMILES: COC(=O)C#CC(=O)OC
• InChI: InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
• InChIKey: VHILMKFSCRWWIJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dimethyl but-2-ynedioate
• IUPAC Traditional name: 1,4-dimethyl but-2-ynedioate
• Synonyms: Dimethyl 2-butynedioate; Dimethyl acetylenedicarboxylate; DMAD; Acetylenedicarboxylic; acid dimethyl ester; Dimethyl acetylenedicarboxylate; Acetylenedicarboxylic acid dimethyl ester; Butynedioic acid dimethyl ester; Dimethyl acetylenedicarboxylate; Dimethyl but-2-yne-1,4-dioate; dimethyl but-2-ynedioate; 丁炔二酸二甲酯

Database IDs

• CAS Number: 10227-18-6; 762-42-5
• EC Number: 212-098-4
• MDL Number: MFCD00008456
• Beilstein Number: 607063
• PubChem SID: 162043261; 24845139; 24893421
• PubChem CID: 12980
• Chemspider ID: 12440
• Wikipedia Title: Dimethyl_acetylenedicarboxylate

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.9685472
• LogD (pH = 7.4): 0.9685472
• Log P: 0.9685472
• Molar Refractivity: 32.5402 cm^3
• Polarizability: 12.367345 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water; Soluble in most; organic solvents
• Apperance: Colorless liquid
• Melting Point: -18 - -16°C; -18°C; -18°C; c
• Boiling Point: 195–198 °C; 96–98° at 8 mm Hg; 195-198°C; 95-98 °C/19 mmHg(lit.); 95-98°C/19mm
• Flash Point: 186.8 °F; 187 °F; 86 °C; 86°C; 86°C(186°F)
• Density: 1.156; 1.156 g/mL at 25 °C(lit.); 1.1564 g/cm3
• Refractive Index: 1.447; 1.4470; 1.4480; n20/D 1.447; n20/D 1.447(lit.)
• Hydrophobicity(logP): -0.09

Safety Information

• Storage Warning: Corrosive/Harmful/Air Sensitive/Light Sensitive/Lachrymatory/Keep Cold/Store under Argon; Light Sensitive
• RTECS: ES0175000
• European Hazard Symbols: Corrosive (C); X
• UN Number: 3265; UN1760
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 21/22-34; 34; R34
• Safety Statements: 23-26-27-36/37/39-45; 26-36/37/39-45; S23 S26 S27; S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• Main Hazard: Toxic gas
• GHS Hazard statements: H302-H314; H314-H318-H302-H227
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

Product Information

• Purity: ≥96.0% (GC); 95%; 97%; 98%; 99%
• Grade: purum
• Linear Formula: CH3OCOC≡CCO2CH3

DETAILS

Sigma Aldrich - D138401

Packaging
5, 25 g in glass bottle
Application
Versatile dienophile used in Diels-Alder reactions.1,2,3

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.