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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
Pricing and availability is not currently available.

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.)

functional group

aldehyde

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)[1].
Used to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.[2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000245194
0000245193
0000208473
0000197353
0000139477

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Wang, Z. et al
Tetrahedron Letters, 41, 4007-4007 (2000)
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
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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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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