| Identification | More | [Name]
1,1-Cyclopropanedicarboxylic acid | [CAS]
598-10-7 | [Synonyms]
1,1-CYCLOPROPANEDICARBOXYLIC ACID
CYCLOPROPANE-1,1-DICARBOXYLIC ACID
RARECHEM AL BO 0836
1,1-CyclopropanedicarboxylicAcid,97%
Cycloprpopane-1,1-Dicarboxylic
Cyclopropane-1,1-dicarboxylic acid 97%
1,1-cyclopropanedicarboxylate
1-Carboxycyclopropanecarboxylic acid | [EINECS(EC#)]
209-917-2 | [Molecular Formula]
C5H6O4 | [MDL Number]
MFCD00013727 | [Molecular Weight]
130.1 | [MOL File]
598-10-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to almost white crystalline powder | [Melting point ]
134-136 °C(lit.)
| [Boiling point ]
200.75°C (rough estimate) | [density ]
1.3985 (rough estimate) | [refractive index ]
1.5800 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
methanol: soluble1g/10 mL, clear, colorless | [form ]
powder to crystal | [pka]
1.82(at 25℃) | [color ]
White to Almost white | [Water Solubility ]
Soluble | [BRN ]
1864823 | [InChI]
InChI=1S/C5H6O4/c6-3(7)5(1-2-5)4(8)9/h1-2H2,(H,6,7)(H,8,9) | [InChIKey]
FDKLLWKMYAMLIF-UHFFFAOYSA-N | [SMILES]
C1(C(O)=O)(C(O)=O)CC1 | [CAS DataBase Reference]
598-10-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314 | [Precautionary statements ]
P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363 | [Hazard Codes ]
Xi,C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29172090 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
white to almost white crystalline powder | [Uses]
1,1-Cyclopropanedicarboxylic acid is used to prepare spiro-cyclopropyl metallocycles.1
| [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. | [Synthesis]
GENERAL STEPS: 15 g of diethyl malonate was dissolved in 187 ml of aqueous solution containing 50 μl NaOH at room temperature. Subsequently 21.3 g (93.8 mmol) of benzyltriethylammonium chloride was added and the resulting mixture was stirred for 10 minutes. To the reaction solution was added 12.3 g (65.47 mmol) of 1,2-dibromoethane and the reaction mixture continued to be stirred at room temperature for more than 18 hours. Upon completion of the reaction, the reaction mixture was neutralized by adding acid solution dropwise. The reaction mixture was washed with aqueous sulfuric acid solution and subsequently extracted with ethyl acetate. The organic phases were combined and the solvent was removed by distillation under reduced pressure to afford 6.2 g of a white solid product, 1,1-cyclopropanedicarboxylic acid, in 76.1% yield. | [Purification Methods]
Recrystallise the di-acid from CHCl3, EtOAc or *C6H6/Et2O/pet ether. It forms a monohydrate. [Nicolet & Satler J Am Chem Soc 49 2070 1927, Beilstein 9 II 512, 9 III 3795.] | [References]
[1] Organic Letters, 2015, vol. 17, # 11, p. 2618 - 2621
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3353 - 3358
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6674 - 6679
[4] Mendeleev Communications, 2014, vol. 24, # 6, p. 345 - 345
[5] Patent: WO2005/79812, 2005, A1. Location in patent: Page/Page column 51 |
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