1,5-dimethyl 3-oxopentanedioate

• ChemBase ID: 69503
• Molecular Formular: C7H10O5
• Molecular Mass: 174.1513
• Monoisotopic Mass: 174.05282342
• SMILES: C(C(=O)CC(=O)OC)C(=O)OC
• Canonical SMILES: COC(=O)CC(=O)CC(=O)OC
• InChI: InChI=1S/C7H10O5/c1-11-6(9)3-5(8)4-7(10)12-2/h3-4H2,1-2H3
• InChIKey: RNJOKCPFLQMDEC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,5-dimethyl 3-oxopentanedioate
• IUPAC Traditional name: 1,5-dimethyl 3-oxopentanedioate
• Synonyms: ACETONEDICARBOXYLIC ACID, DIMETHYLESTER; Dimethyl-3-oxoglutarate; Dimethyl-1,3-acetonedicarboxylate; Acetone-1,3-dicarboxylic acid dimethyl ester; Dimethyl 3-oxoglutarate; Dimethyl acetone-1,3-dicarboxylate; Dimethyl acetone-1,3-dicarboxylate; Dimethyl 3-oxopentane-1,5-dioate; Dimethyl acetone-1,3-dicarboxylate; Dimethyl-3-oxoglutarate; dimethyl 3-oxopentanedioate; 3-氧代戊二酸二甲酯; 1,3-丙酮二羧酸二甲酯; 丙酮二羧酸二甲酯

Database IDs

• CAS Number: 1830-54-2
• EC Number: 217-385-8
• MDL Number: MFCD00008462
• Beilstein Number: 1366042
• PubChem SID: 24893418; 162035229
• PubChem CID: 74591

CALCULATED PROPERTIES

• Acid pKa: 9.98486
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.41584393
• LogD (pH = 7.4): 0.41473073
• Log P: 0.18252482
• Molar Refractivity: 38.4212 cm^3
• Polarizability: 15.412765 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 16-17°C; 16-17°C
• Boiling Point: 237-241 °C/760 mmHg(lit.); 237-241°C; 237-241°C
• Flash Point: >110°C; >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.185; 1.206 g/mL at 20 °C(lit.)
• Refractive Index: 1.4440; n20/D 1.444(lit.); n20/D 1.445

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 43
• Safety Statements: 24-37; 36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280; P280G-P262
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); 95%; 95+%; 96%; 97%; TECH
• Grade: Lonza quality; purum
• Impurities: ≤0.3% impurity, main unknown; ≤0.5% trimethyl citrate; ≤1.0% methyl acetoacetate; ≤5.0% 1,3-di-MeO-carbonyl-2-MeO-propene
• Quality: dist.
• Linear Formula: CO(CH2COOCH3)2

DETAILS

MP Biomedicals - 05212340

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 690856

Packaging
1 kg in poly bottle
25 kg in comp drum

Sigma Aldrich - D138002

Packaging
25, 100 g in glass bottle

REFERENCES

• Reacts with ɑ-diketones in aqueous buffer to give bicyclic diketones (Weiss-Cook condensation): Tetrahedron Lett., 4885 (1968); Org. Synth. Coll., 7, 50 (1990):
  
• See also: J. Chem. Soc., Perkin 1, 1425 (1997). Use of cyclic ɑ-diketones leads to propellanes: Can. J. Chem., 189 (1978).
• The Na salt (NaH/THF) reacts with alkynals: J. Org. Chem., 62, 5688 (1997), or ynones: Synth. Commun., 28, 1525 (1998), under mild conditions to give 4-substituted dimethyl 2-hydroxyisophthalates via a Michael addition - aldol cyclization process; see 3-Butyn-2-one, L05527 for scheme.
• See also Diethyl acetone-1,3-dicarboxylate, A10933.