1,3-diethyl 2,2-dibromopropanedioate

• ChemBase ID: 89111
• Molecular Formular: C7H10Br2O4
• Molecular Mass: 317.9599
• Monoisotopic Mass: 315.8945828
• SMILES: O(C(=O)C(C(=O)OCC)(Br)Br)CC
• Canonical SMILES: CCOC(=O)C(C(=O)OCC)(Br)Br
• InChI: InChI=1S/C7H10Br2O4/c1-3-12-5(10)7(8,9)6(11)13-4-2/h3-4H2,1-2H3
• InChIKey: PFZYFZRUPFUEOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2,2-dibromopropanedioate
• IUPAC Traditional name: 1,3-diethyl 2,2-dibromopropanedioate
• Synonyms: Dibromomalonic acid diethyl ester; Diethyl 2,2-dibromopropane-1,3-dioate; Diethyl 2,2-dibromomalonate; Diethyl dibromomalonate; 二溴丙二酸二乙酯

Database IDs

• CAS Number: 631-22-1
• EC Number: 211-151-9
• MDL Number: MFCD00015154
• Beilstein Number: 1783879
• PubChem SID: 24865820; 162075995
• PubChem CID: 69427

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9222991
• LogD (pH = 7.4): 1.9222991
• Log P: 1.9222991
• Molar Refractivity: 53.6122 cm^3
• Polarizability: 21.331919 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 108-110°C/4mm; 108-110°C/4mm; 140-143 °C/18 mmHg(lit.)
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.68; 1.68 g/mL at 25 °C(lit.); 1.680
• Refractive Index: 1.4850; n20/D 1.484(lit.)

Safety Information

• Storage Warning: Corrosive/Light Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: UN1760
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 95+%; 97%
• Linear Formula: Br2C(CO2C2H5)2

DETAILS

Sigma Aldrich - 412708

Packaging
25 mL in glass bottle

REFERENCES

• Brominating agent for Li enolates of esters, by displacement of bromomalonate, giving better results than bromine itself where unsaturation is present: Rec. Trav. Chim., 96, 72 (1977).
• A so-called 'forcing Knoevenagel' methodology has been employed with ketones in the presence of tributylantimony to give the alkylidenemalonates: Tetrahedron, 51, 8033 (1995). Under similar conditions, Michael acceptors were found to undergo cyclopropanation of the olefinic double bond: Tetrahedron, 45, 3011 (1989).