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Sigma-Aldrich

Cyclopropane-1,1-dicarboxylic acid

97%

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About This Item

Linear Formula:
C3H4(CO2H)2
CAS Number:
598-10-7
Molecular Weight:
130.10
Beilstein:
1864823
EC Number:
209-917-2
MDL number:
MFCD00013727
UNSPSC Code:
12352100
PubChem Substance ID:
24861158
NACRES:
NA.22

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
Tetrahedron, 45, 1219-1219 (1989)
Nora A Foroud et al.
Phytopathology, 109(5), 796-803 (2018-12-13)
Plant signaling hormones such as ethylene have been shown to affect the host response to various pathogens. Often, the resistance responses to necrotrophic fungi are mediated through synergistic interactions of ethylene (ET) with the jasmonate signaling pathway. On the other
Y H Dong et al.
Science in China. Series B, Chemistry, life sciences & earth sciences, 33(11), 1297-1303 (1990-11-01)
The crystal structures of [Pt(NH3)2CPrDCA].H2O (I), [Pt(CH3NH2)2CPrDCA] (II), and [Pt(dmbn) CPrDCA].2.5H2O (III) (where CPrDCA is 1,1-cyclopropanedicarboxylate; dmbn is 2,3-dimethyl-2,3-butyldiamine) are determined. Compound I crystallizes in the orthorhombic space group Pnma with the cell dimensions: a = 6.517(2), b = 9.709(3)
A Hussain K Sharba et al.
Molecules (Basel, Switzerland), 10(9), 1153-1160 (2007-11-17)
New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl)
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