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Diethyl 1,1-cyclopropanedicarboxylate

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Name

Diethyl 1,1-cyclopropanedicarboxylate

EINECS 216-321-6
CAS No. 1559-02-0 Density 1.164 g/cm3
PSA 52.60000 LogP 0.89280
Solubility N/A Melting Point 134-136 °C(lit.)
Formula C9H14O4 Boiling Point 219.2 °C at 760 mmHg
Molecular Weight 186.208 Flash Point 86.7 °C
Transport Information N/A Appearance clear colorless liquid
Safety 26-36-24/25-23 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1559-02-0 (Diethyl 1,1-cyclopropanedicarboxylate) Hazard Symbols IrritantXi
Synonyms

1,1-Cyclopropanedicarboxylicacid, diethyl ester (6CI,7CI,8CI,9CI);1,1-Bis(ethoxycarbonyl)cyclopropane;1,1-Dicarbethoxycyclopropane;Ethyl1,1-cyclopropanedicarboxylate;NSC 21376;

Article Data 62

Diethyl 1,1-cyclopropanedicarboxylate Synthetic route

106-93-4

ethylene dibromide

105-53-3

diethyl malonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;98%
With potassium carbonate; [bmim]Br In N,N-dimethyl-formamide at 20 - 70℃;94%
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dimethyl sulfoxide at 20℃; for 24h; Alkylation; Cyclization;92%
105-53-3

diethyl malonate

diphenyl(vinyl)sulfonium trifluoromethanesulfonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h;97%
107-06-2

1,2-dichloro-ethane

105-53-3

diethyl malonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide Reflux;93%
With water; potassium carbonate; tetrabutylammomium bromide In benzene at 80℃; for 12h;85%
With tetrabutylammomium bromide; potassium carbonate at 120℃; Concentration; Temperature;83.47%
584-08-7

potassium carbonate

106-93-4

ethylene dibromide

105-53-3

diethyl malonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide88.7%
624-73-7

1,2-Diiodoethane

105-53-3

diethyl malonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium hydrogencarbonate Reflux;80.77%
64648-13-1, 81115-85-7, 81115-90-4

S-Ethenyl-S-(4-methylphenyl)-N-tolylsulfilimine

105-53-3

diethyl malonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 24h; Addition;76%
56692-06-9

S-ethenyl-S-phenyl-N-(toluene-4-sulfonyl)sulfilimine

105-53-3

diethyl malonate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 24h; Addition;35%
106-93-4

ethylene dibromide

105-53-3

diethyl malonate

A

75-21-8

oxirane

B

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 13%
C n/a
110-86-1

pyridine

18721-64-7

diethyl 2-(2-bromoethyl)-malonate

75-36-5

acetyl chloride

108-88-3

toluene

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

18721-64-7

diethyl 2-(2-bromoethyl)-malonate

141-52-6

sodium ethanolate

1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

Diethyl 1,1-cyclopropanedicarboxylate Specification

The Diethyl cyclopropane-1,1-dicarboxylate is an organic compound with the formula C9H14O4. The IUPAC name of this chemical is diethyl cyclopropane-1,1-dicarboxylate. With the CAS registry number 1559-02-0, it is also named as 1,1-cyclopropanedicarboxylic acid, diethyl ester. The product's categories are Cyclopropanes; Simple 3-Membered Ring Compounds; Cycloalkanes; C8 to C9; Carbonyl Compounds; Esters. Besides, it is a clear colorless liquid, which should be stored in a cool and dry place.

Physical properties about Diethyl cyclopropane-1,1-dicarboxylate are: (1)ACD/LogP: 1.18; (2)ACD/LogD (pH 5.5): 1.18; (3)ACD/LogD (pH 7.4): 1.18; (4)ACD/BCF (pH 5.5): 4.67; (5)ACD/BCF (pH 7.4): 4.67; (6)ACD/KOC (pH 5.5): 104.94; (7)ACD/KOC (pH 7.4): 104.94; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 52.6 Å2; (11)Index of Refraction: 1.473; (12)Molar Refractivity: 44.9 cm3; (13)Molar Volume: 159.9 cm3; (14)Polarizability: 17.8×10-24cm3; (15)Surface Tension: 42.4 dyne/cm; (16)Density: 1.164 g/cm3; (17)Flash Point: 86.7 °C; (18)Enthalpy of Vaporization: 45.56 kJ/mol; (19)Boiling Point: 219.2 °C at 760 mmHg; (20)Vapour Pressure: 0.121 mmHg at 25°C.

Preparation: this chemical can be prepared by 1,2-dibromo-ethane and malonic acid diethyl ester. This reaction will need reagent NaOEt and solvent ethanol. The yield is about 52%.



Uses of Diethyl cyclopropane-1,1-dicarboxylate: it can be used to produce cyclopropane-1,1-diyl-bis-methanol. It will need reagent LiAlH4 and diethyl ether.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with skin and eyes In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)C1(C(=O)OCC)CC1
(2)InChI: InChI=1/C9H14O4/c1-3-12-7(10)9(5-6-9)8(11)13-4-2/h3-6H2,1-2H3
(3)InChIKey: KYYUCZOHNYSLFV-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C9H14O4/c1-3-12-7(10)9(5-6-9)8(11)13-4-2/h3-6H2,1-2H3
(5)Std. InChIKey: KYYUCZOHNYSLFV-UHFFFAOYSA-N

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