343412

Sigma-Aldrich

Cyclopropane-1,1-dicarboxylic acid

97%

Linear Formula:
C3H4(CO2H)2
CAS Number:
Molecular Weight:
130.10
Beilstein/REAXYS Number:
1864823
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

mp

134-136 °C (lit.)

solubility

methanol: soluble 1 g/10 mL, clear, colorless

SMILES string

OC(=O)C1(CC1)C(O)=O

InChI

1S/C5H6O4/c6-3(7)5(1-2-5)4(8)9/h1-2H2,(H,6,7)(H,8,9)

InChI key

FDKLLWKMYAMLIF-UHFFFAOYSA-N

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General description

Cyclopropane-1,1-dicarboxylic acid is a dicarboxylic acid. Cyclopropane-1,1-dicarboxylic acid, an inhibitor of 1-aminocyclopropane-1-carboxylic acid oxidase, was quantitated in Lycopersicum esculentum by HPLC-electrospray tandem mass spectrometry. Crystal and molecular structure of cyclopropane-1,1-dicarboxylic acid has been reported.

Application

Cyclopropane-1,1-dicarboxylic acid was used in the preparation of new heterocyclic derivatives of cyclopropane dicarboxylic acid containing thiadiazole and 1,2,4-triazole moieties. It was also used to prepare spiro-cyclopropyl metallocycles.

Packaging

5 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

C

Risk Statement

34

Safety Statement

26-36/37/39-45

RIDADR

UN 3261 8 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Michael B Johansen et al.
Organic letters, 10(16), 3497-3500 (2008-07-12)
Pyrrolo[1,2- a]indoles are conveniently prepared from tetrahydro-1,2-oxazines, which in turn are generated through the reaction of nitrones with 1,1-cyclopropanediesters. The synthetic route proves to be highly diastereoselective and provides access to the core of the recently discovered pyrrolo[1,2- a]indole natural...
Yan-Biao Kang et al.
Organic & biomolecular chemistry, 4(2), 299-301 (2006-01-05)
A tandem ring-opening-cyclization reaction of cyclopropanes with imines in the presence of 5 mol% of scandium triflate was developed for the highly diastereoselective synthesis of multi-substituted pyrrolidines.
Konstantinos Petritis et al.
Phytochemical analysis : PCA, 14(6), 347-351 (2003-12-12)
Varying concentrations of cyclopropane-1,1-dicarboxylic acid (CDA), an inhibitor of 1-aminocyclopropane-1-carboxylic acid oxidase, added to the solid culture medium of tomato nodal shoot segments resulted in a reduction in the level of endogenous ethylene according to the concentration of inhibitor applied....
Tetrahedron, 45, 1219-1219 (1989)
The crystal and molecular structure of cyclopropane-1, 1-dicarboxylic acid.
Meester MAM, et al.
Acta Crystallographica Section B, Structural Science, 27(3), 630-634 (1971)

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