Cyclopropanecarboxaldehyde, 98%
Cyclopropanecarboxaldehyde, 98%
Cyclopropanecarboxaldehyde, 98%
Cyclopropanecarboxaldehyde, 98%
Thermo Scientific Chemicals

Cyclopropanecarboxaldehyde, 98%

CAS: 1489-69-6 | C4H6O | 70.091 g/mol
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Catalog number L14931.03
also known as L14931-03
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Chemical Identifiers
CAS1489-69-6
IUPAC Namecyclopropanecarbaldehyde
Molecular FormulaC4H6O
InChI KeyJMYVMOUINOAAPA-UHFFFAOYSA-N
SMILESO=CC1CC1
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SpecificationsSpecification SheetSpecification Sheet
Assay (GC)≥97.5%
Refractive Index1.4275-1.4315 @ 20?C
Appearance (Color)Clear colorless
Free acid (titration)≤1.5%
FormLiquid
Cyclopropanecarboxaldehyde reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides. It is also used in the synthesis of eta(2)-enonenickel complexes by reacting with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene) and PBu(3) and to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Cyclopropanecarboxaldehyde reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides. It is also used in the synthesis of eta(2)-enonenickel complexes by reacting with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene) and PBu(3) and to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.

Solubility
Soluble in water.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature is 2 - 8°C. It is sensitive to air.
RUO – Research Use Only

General References:

  1. Lewis Brewster Young.; Walter S. Trahanovsky. Cerium(IV) oxidation of organic compounds. III. Preparation of cyclopropanecarboxaldehyde from cyclopropanemethanol. J. Org. Chem. 1967, 32 (7), 2349-2350.
  2. J. R. Durig.; Fusheng Feng.; T. S. Little.; Ai -Ying Wang. Conformational stability, barriers to internal rotation, structural parameters, ab initio calculations, and vibrational assignment of cyclopropanecarboxaldehyde. Structural Chemistry. 1992, 3 (6), 417-428.
  3. Reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides: Synth. Commun., 25, 3351 (1995):