1,3-dimethyl propanedioate

• ChemBase ID: 85346
• Molecular Formular: C5H8O4
• Molecular Mass: 132.11462
• Monoisotopic Mass: 132.04225874
• SMILES: O(C(=O)CC(=O)OC)C
• Canonical SMILES: COC(=O)CC(=O)OC
• InChI: InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3
• InChIKey: BEPAFCGSDWSTEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dimethyl propanedioate
• IUPAC Traditional name: dimethyl malonate
• Synonyms: Dimethyl malonate; Propanedioic acid dimethyl ester; Malonic acid dimethyl ester; Dimethyl malonate; 丙二酸二甲酯

Database IDs

• CAS Number: 108-59-8
• EC Number: 203-597-8
• MDL Number: MFCD00008460
• Beilstein Number: 774261
• Merck Index: 146096
• PubChem SID: 24848281; 24882580; 24854457; 162072462
• PubChem CID: 7943
• Chemspider ID: 21106102
• Wikipedia Title: Dimethyl_malonate

CALCULATED PROPERTIES

• Acid pKa: 12.90322
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.039329175
• LogD (pH = 7.4): -0.03933052
• Log P: -0.039329156
• Molar Refractivity: 28.526 cm^3
• Polarizability: 11.623122 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly soluble in water
• Apperance: Colorless liquid
• Melting Point: -62 - -60°C; -62 °C(lit.); -62°C; -62°C
• Boiling Point: 180-181 °C(lit.); 180-181°C; 180–181 °C; 180-181°C
• Flash Point: 185 °F; 85 °C; 85°C; 90°C(194°F)
• Density: 1.154; 1.156; 1.156 g/mL at 25 °C(lit.)
• Refractive Index: 1.4130; n20/D 1.413; n20/D 1.413(lit.)
• Vapor Density: >1 (vs air)
• Hydrophobicity(logP): 0.069

Safety Information

• Storage Warning: Irritant
• RTECS: OO0950000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 15; 26-36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H227; H315-H319-H335
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥96.0% (GC); ≥99%; 95%; 98%; 98+%
• Grade: purum
• Linear Formula: CH2(COOCH3)2

DETAILS

Sigma Aldrich - 136441

Packaging
1 kg in glass bottle
250 g in glass bottle

REFERENCES

• For successive C-alkylation, using NaOMe/MeOH, followed by NaH/THF, see: Org. Synth. Coll., 8, 381 (1993). For Michael addition to ɑ?-unsaturated acids, catalyzed by the Li salt of L-proline, see: J. Chem. Soc., Chem. Commun., 1088 (1991). For Knoevenagel reaction with (R)-citronellal, catalyzed by piperidine/AcOH, to give the alkylidene derivative, see: Org. Synth. Coll., 9, 310 (1998).
• C-Arylation with ortho-nitroaryl halides can be accomplished with NaH in DMSO. The products can be readily converted to substituted oxindoles: Synthesis, 51 (1993):
  
• Arylation with benzene: Tetrahedron Lett., 27, 2763 (1986), and free-radical substitution with thiophene or furan at the 2-position: Heterocycles, 27, 2627 (1988), are promoted by Ce(IV) salts.
• See also Diethyl malonate, A15468.