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1489-69-6 - Cyclopropanecarboxaldehyde, 98% - L14931 - Alfa Aesar

L14931 Cyclopropanecarboxaldehyde, 98%

CAS Number
1489-69-6
Synonyms

Size Price ($) Quantity Availability
1g 31.86
5g 106.53
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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
Sensitivity
Air Sensitive
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-H318

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. 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 IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

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

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