2-bromopropanedial

• ChemBase ID: 64245
• Molecular Formular: C3H3BrO2
• Molecular Mass: 150.95872
• Monoisotopic Mass: 149.93164134
• SMILES: O=CC(C=O)Br
• Canonical SMILES: O=CC(C=O)Br
• InChI: InChI=1S/C3H3BrO2/c4-3(1-5)2-6/h1-3H
• InChIKey: SURMYNZXHKLDFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromopropanedial
• IUPAC Traditional name: 2-bromopropanedial
• Synonyms: Bromomalonaldehyde; 2-Bromomalonaldehyde; 2-Bromo-propanedial; 2-Bromo-1,3-propanedialdehyde; Bromomalonaldehyde; 2-Bromomalonaldehyde; 2-bromopropanedial; 溴代丙二醛

Database IDs

• CAS Number: 2065-75-0
• MDL Number: MFCD00459999
• PubChem SID: 24878070; 162029984
• PubChem CID: 74945

CALCULATED PROPERTIES

• Acid pKa: 4.4680343
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.89006907
• LogD (pH = 7.4): -2.5212631
• Log P: 0.17657888
• Molar Refractivity: 24.5097 cm^3
• Polarizability: 9.544977 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 132 - 134°C; 132-136 °C(lit.)
• Hydrophobicity(logP): -0.314

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%
• Linear Formula: BrCH(CHO)2

DETAILS

Sigma Aldrich - 535079

Application
Used in the formation of glyoxal-derived adducts from substituted guanines1
Used to construct a 1,4-dihydroquinoline bearing a C-3 chiral sulfoxide group which functions as an annelated NADH model in the enantioselective reduction of methyl benzoylformate to methyl mandelate.
Packaging
5, 25 g in glass bottle

REFERENCES

• Cuny, G., et al.: Bioorg. Med. Chem. Lett., 18, 4388 (2008)
• Frotscher, M., et al.: J. Med. Chem., 51, 2158 (2008)