Cyclopropane-1,1-dicarboxylic acid

Name: Cyclopropane-1,1-dicarboxylic acid
Brand: ALDRICH
Price: 210 USD
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97%

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About This Item

Linear Formula:

C₃H₄(CO₂H)₂

CAS Number:

598-10-7

Molecular Weight:

130.10

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24861158

EC Number:

209-917-2

Beilstein/REAXYS Number:

1864823

MDL number:

MFCD00013727

Assay:

97%

Key Documents

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InChI key

FDKLLWKMYAMLIF-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

97%

mp

134-136 °C (lit.)

solubility

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

functional group

carboxylic acid

Quality Level

200

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1 of 4

This Item	143510	28684	28682
Sigma-Aldrich 343412 Cyclopropane-1,1-dicarboxylic acid	Sigma-Aldrich 143510 5-Hydroxyindole-2-carboxylic acid	Sigma-Aldrich 28684 trans-Cyclobutane-1,2-dicarboxylic acid	Sigma-Aldrich 28682 cis-Cyclobutane-1,2-dicarboxylic acid
assay 97%	assay ≥96.5%	assay ≥97.0% (T)	assay ≥97.0% (T)
solubility methanol: soluble 1 g/10 mL, clear, colorless	solubility chloroform/ethanol (1:1): soluble 50 mg/mL, clear to slightly hazy, yellow to brown	solubility -	solubility -
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 100
mp 134-136 °C (lit.)	mp 249 °C (dec.) (lit.)	mp -	mp 133-139 °C
functional group carboxylic acid	functional group carboxylic acid	functional group carboxylic acid	functional group carboxylic acid

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.[1] Crystal and molecular structure of cyclopropane-1,1-dicarboxylic acid has been reported.[2]

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.[3] It was also used to prepare spiro-cyclopropyl metallocycles.[4]

pictograms

GHS05

signalword

Danger

hcodes

H314

pcodes

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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)

Synthesis of thiadiazoles and 1,2,4-triazoles derived from cyclopropane dicarboxylic acid.

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)

Studies on structures of some platinum complexes with 1,1-cyclopropanedicarboxylate.

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)

Expedient synthesis of pyrrolo[1,2-a]indoles: preparation of the core of yuremamine.

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

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