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L14931 Cyclopropanecarboxaldehyde, 98%

CAS Number
1489-69-6
Synonyms

Stock No. Size Price ($) Quantity Availability
L14931-03 1g 34.90
L14931-06 5g 116.00
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Cyclopropanecarboxaldehyde, 98%

MDL
MFCD00012261
EINECS
000-000-0

Chemical Properties

Formula
C4H6O
Formula Weight
70.09
Boiling Point
98-101°
Flash Point
7°(44°F)
Density
0.938
Refractive Index
1.4298
Storage & Sensitivity
Air Sensitive. Store under Argon. Ambient temperatures.
Solubility
Soluble in water.

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.

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.

Literature References

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.

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.

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):

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H314-H335

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
906781
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2912.29
TSCA
Yes
RTECS
GZ1005000

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