Cyclopropane-1,1-dicarboxylic acid

Base Information

• Chemical Name: Cyclopropane-1,1-dicarboxylic acid
• CAS No.: 598-10-7
• Molecular Formula: C5H6O4
• Molecular Weight: 130.1
• Hs Code.: 29172090
• European Community (EC) Number: 209-917-2
• NSC Number: 626865
• DSSTox Substance ID: DTXSID20208526
• Nikkaji Number: J6.789J
• Wikidata: Q72460599
• ChEMBL ID: CHEMBL1993862
• Mol file: 598-10-7.mol

Synonyms:1,1-cyclopropanedicarboxylate;CPrDCA

Chemical Property of Cyclopropane-1,1-dicarboxylic acid

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 1.56E-06mmHg at 25°C
• Melting Point: 134-136 °C(lit.)
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 371.307 °C at 760 mmHg
• PKA: 1.82(at 25℃)
• Flash Point: 192.54 °C
• PSA: 74.60000
• Density: 1.708 g/cm³
• LogP: -0.06420
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: methanol: soluble1g/10 mL, clear, colorless
• Water Solubility.: Soluble
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 130.02660867
• Heavy Atom Count: 9
• Complexity: 152

Purity/Quality:

99% ^*data from raw suppliers

1,1-Cyclopropanedicarboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1(C(=O)O)C(=O)O
• Uses: 1,1-Cyclopropanedicarboxylic acid is used to prepare spiro-cyclopropyl metallocycles.1 1,1-Cyclopropanedicarboxylic acid, is used as 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. 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. It can also be used as a building block for the synthesis of a series of cyclopropanecarboxamides, having antifungal activity.

Technology Process of Cyclopropane-1,1-dicarboxylic acid

There total 19 articles about Cyclopropane-1,1-dicarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.7%

tert-butyl methyl ether (1634-04-4) → cyclopropane-1,1-dicarboxylic acid (598-10-7)

Guidance literature:

In water;

Reference yield: 89.0%

C13H14O5 (1247181-41-4) + C13H14O5 (1247181-42-5) → phenylethane 1,2-diol (93-56-1) + cyclopropane-1,1-dicarboxylic acid (598-10-7)

Guidance literature:

With sodium hydroxide; at 60 ℃; for 4h;

DOI:10.1021/ol3030154

Reference yield: 87.2%

→ cyclopropane-1,1-dicarboxylic acid (598-10-7)

Guidance literature:

upstream raw materials:

diethyl cyclopropane-1,1-dicarboxylate

1-carbethoxy-1-cyanocyclopropane

1-cyano-cyclopropanecarboxylic acid

N,N'-bis(phenyl)cyclopropane-1,1-diamide

Downstream raw materials:

4-butanolide

cyclopropanecarboxylic acid

4-hydroxybutanoic acid

diethyl cyclopropane-1,1-dicarboxylate

Refernces

• 1、 Zhen, Xiaohua,Wan, Xintong,Zhang, Wei,Li, Qiao,Zhang-Negrerie, Daisy,Du, Yunfei. "Synthesis of Spirooxindoles from N-Arylamide Derivatives via Oxidative C(sp2)-C(sp3) Bond Formation Mediated by PhI(OMe)2 Generated in Situ". . p. 890 - 894. Retrieved 2019.
• 2、 Shi, Wei,Qiang, Hao,Huang, Dandan,Bi, Xinzhou,Huang, Wenlong,Qian, Hai. "Exploration of novel pyrrolo[2,1-f][1,2,4]triazine derivatives with improved anticancer efficacy as dual inhibitors of c-Met/VEGFR-2". . p. 814 - 831. Retrieved 2018/09/29.