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272213

Sigma-Aldrich

Cyclopropanecarboxaldehyde

98%

Synonym(s):

1-(Formyl)cyclopropane, 2-Cyclopropanecarboxaldehyde, Cyclopropanecarbaldehyde, Cyclopropylcarboxaldehyde, Formylcyclopropane

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About This Item

Linear Formula:
C3H5CHO
CAS Number:
1489-69-6
Molecular Weight:
70.09
MDL number:
MFCD00012261
UNSPSC Code:
12352100
PubChem Substance ID:
24856460
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.4298 (lit.)

bp

98-101 °C (lit.)

density

0.938 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

O=CC1CC1

InChI

1S/C4H6O/c5-3-4-1-2-4/h3-4H,1-2H2

InChI key

JMYVMOUINOAAPA-UHFFFAOYSA-N

Application

Cyclopropanecarboxaldehyde was used in the synthesis of eta(2)-enonenickel complexes by reacting with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene) and PBu(3).
Used to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225,H314

Hazard Classifications

Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

44.6 °F - closed cup

Flash Point(C)

7 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Barry M Trost et al.
Journal of the American Chemical Society, 128(41), 13328-13329 (2006-10-13)
Transition-metal-catalyzed trimethylenemethane (TMM) [3 + 2] cycloadditions provide direct routes to functionalized cyclopentanes. This reaction has been shown to be a highly chemo-, regio-, and diastereoselective process. We report a palladium-catalyzed asymmetric [3 + 2] trimethylenemethane (TMM) cycloaddition between 3-acetoxy-2-trimethylsilylmethyl-1-propene
Wang, Z. et al
Tetrahedron Letters, 41, 4007-4007 (2000)
M Cowart et al.
Bioorganic & medicinal chemistry letters, 11(1), 83-86 (2001-01-05)
The synthesis and SAR of a novel series of non-nucleoside pyridopyrimidine inhibitors of the enzyme adenosine kinase (AK) are described. It was found that pyridopyrimidines with a broad range of medium and large non-polar substituents at the 5-position potently inhibited
Krzysztof Z Łączkowski et al.
Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, 27(9), 2125-2140 (2018-09-18)
Synthesis and investigation of antifungal, anticonvulsant and anti-Toxoplasma gondii activities of ten novel (2-(cyclopropylmethylidene)hydrazinyl)thiazole 3a-3j are presented. Among the derivatives, compounds 3a-3d and 3f-3j possess very high activity against Candida spp. ATCC with MIC = 0.015-7.81 µg/ml. Compounds 3a-3d and 3f-3j possess also
Takashi Tamaki et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(39), 10083-10091 (2009-09-01)
Cyclopropanecarboxaldehyde (1 a), cyclopropyl methyl ketone (1 b), and cyclopropyl phenyl ketone (1 c) were reacted with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene) and PBu(3) at 100 degrees C to give eta(2)-enonenickel complexes (2 a-c). In the presence of PCy(3) (Cy =

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