magnesium(2+) ion ethoxyethane dibromide

• ChemBase ID: 302425
• Molecular Formular: C4H10Br2MgO
• Molecular Mass: 258.2346
• Monoisotopic Mass: 255.89488064
• SMILES: CCOCC.[Mg+2].[Br-].[Br-]
• Canonical SMILES: CCOCC.[Mg+2].[Br-].[Br-]
• InChI: InChI=1S/C4H10O.2BrH.Mg/c1-3-5-4-2;;;/h3-4H2,1-2H3;2*1H;/q;;;+2/p-2
• InChIKey: JGZKUKYUQJUUNE-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: magnesium(2+) ion ethoxyethane dibromide
• IUPAC Traditional name: magnesium(2+) ion diethyl ether dibromide
• Synonyms: Magnesium bromide diethyl etherate; 乙醚溴化镁

Database IDs

• CAS Number: 29858-07-9
• MDL Number: MFCD00064500

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.83816534
• LogD (pH = 7.4): 0.83816534
• Log P: 0.83816534
• Molar Refractivity: 22.5097 cm^3
• Polarizability: 8.788117 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 35°C(95°F)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Flammable (F)
• UN Number: UN1325
• Hazard Class: 4.1
• Packing Group: II
• Risk Statements: 11
• Safety Statements: 7-16-33
• TSCA Listed: 否
• GHS Pictograms: GHS02
• GHS Hazard statements: H228
• GHS Precautionary statements: P210-P241-P280-P240-P370+P378A

Product Information

• Purity: 98%

REFERENCES

• Lewis acid which can influence the regio- and stereochemical outcome of reactions because of its chelating character. Mediates the rearrangement of epoxides to aldehydes and ketones: J. Am. Chem. Soc., 77, 5083 (1955); Tetrahedron Lett., 33, 4457 (1992); or ring-opening to bromohydrins: J. Org. Chem., 61, 3557 (1996); 68, 3660 (2003); Tetrahedron Lett., 45, 5969 (2004). Promotes anti-selectivity in aldol reactions: J. Org. Chem., 56, 5978 (1991). Activates amides to selective N-acylation: Tetrahedron Lett., 43, 647 (2002).
• In combination with Me₂S, promotes chemoselective deprotection of p-methoxybenzyl ethers, in the presence of benzyl or TBDMS ethers, benzoate esters or acetonides: Tetrahedron Lett., 38, 1443 (1997). In the presence of triethylamine, promotes the room-temperature Cannizzaro reaction of aryl and heteroaryl aldehydes to the corresponding alcohol and carboxylic acid: Org. Lett., 7, 5893 (2005).
• For a brief feature on uses of this reagent, see: Synlett, 912 (2004).