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Dimethyl furan-2,5-dicarboxylate

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Name

Dimethyl furan-2,5-dicarboxylate

EINECS N/A
CAS No. 4282-32-0 Density 1.244 g/cm3
PSA 65.74000 LogP 0.85280
Solubility N/A Melting Point 112°C
Formula C8H8O5 Boiling Point 270.9 °C at 760 mmHg
Molecular Weight 184.149 Flash Point 117.6 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 4282-32-0 (Dimethyl  Furan-2,5-dicarboxylate) Hazard Symbols N/A
Synonyms

2,5-Furandicarboxylicacid, dimethyl ester (6CI,7CI,8CI,9CI);Dimethyl 2,5-furandicarboxylate;NSC191940;2,5-furandicarboxylic acid, dimethyl ester;

Article Data 88

Dimethyl furan-2,5-dicarboxylate Synthetic route

67-56-1

methanol

3238-40-2

furan-2,5-dicarboxylic acid

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;99%
With aluminum(III) sulphate octadecahydrate at 150℃; for 0.416667h; Sealed tube; Microwave irradiation;98.5%
With gallium(III) triflate at 175℃; for 2h; Reagent/catalyst; Sealed tube; Inert atmosphere;95%
67-56-1

methanol

67-47-0

5-hydroxymethyl-2-furfuraldehyde

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With oxygen at 120℃; under 7500.75 Torr; for 12h; Reagent/catalyst; Autoclave;99%
With oxygen; potassium carbonate at 20℃; under 760.051 Torr; for 3h; Reagent/catalyst; Sealed tube;96%
With oxygen at 80℃; under 1500.15 Torr; for 4h; Reagent/catalyst; Pressure; Temperature; Autoclave;96%
3238-40-2

furan-2,5-dicarboxylic acid

616-38-6

carbonic acid dimethyl ester

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With tetramethylammonium bromide; lithium carbonate In N,N-dimethyl-formamide at 150℃; for 10.5h; Temperature; Reagent/catalyst; Solvent;98.62%
67-56-1

methanol

2527-99-3

methyl 5-bromo-2-furoate

201230-82-2

carbon monoxide

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 100℃; under 4137.29 - 51716.2 Torr; for 15h; Reagent/catalyst; Pressure; Temperature;98.3%
With disodium hydrogenphosphate; triphenylphosphine; palladium dichloride In 1-methyl-pyrrolidin-2-one Schlenk technique;83%
3238-40-2

furan-2,5-dicarboxylic acid

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In diethyl ether at -78℃;98%
823-82-5

2,5-diformylfurane

67-56-1

methanol

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
Stage #1: 2,5-diformylfurane; methanol With sodium cyanide at 20℃; for 0.0833333h; Sealed tube;
Stage #2: With manganese(IV) oxide at 80℃; for 1h; Sealed tube;
97%
With oxygen at 100℃; under 4500.45 Torr; for 12h; Reagent/catalyst;96 %Chromat.
67-56-1

methanol

56-23-5

tetrachloromethane

88-14-2

2-furanoic acid

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With copper acetylacetonate at 150℃; for 6h; Inert atmosphere; Autoclave;95%
67-56-1

methanol

56-23-5

tetrachloromethane

A

611-13-2

2-furoic acid methyl ester

B

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With copper(l) iodide at 120℃; for 6h; Inert atmosphere; Autoclave;A 95%
B 5%
With copper(l) iodide at 140℃; for 0.5h; Inert atmosphere; Autoclave;A 60%
B 40%
67-56-1

methanol

(5-(1,3-dioxan-2-yl)furan-2-yl)methanol

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With oxygen; sodium carbonate at 129.84℃; under 3750.38 Torr; Autoclave;95%
With oxygen; sodium carbonate at 120℃; under 3800.26 Torr; for 15h;85%
67-56-1

methanol

90200-14-9

5-(hydroxymethyl)-2-(dimethoxymethyl)furan

4282-32-0

furan-2,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With oxygen; sodium carbonate at 129.84℃; under 3750.38 Torr; Autoclave;93%

Dimethyl furan-2,5-dicarboxylate Specification

The Dimethyl furan-2,5-dicarboxylate, with the cas registry number 4282-32-0, is also called 2,5-furandicarboxylic acid, dimethyl ester. And the molecular formula of the chemical is C8H8O5.  

The characteristics of this chemical are as followings: (1)ACD/LogP: 0.87; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 5; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 65.74 Å2; (7)Index of Refraction: 1.48; (8)Molar Refractivity: 42.09 cm3; (9)Molar Volume: 148 cm3; (10)Polarizability: 16.68×10-24cm3; (11)Surface Tension: 39.4 dyne/cm; (12)Density: 1.244 g/cm3; (13)Flash Point: 117.6 °C; (14)Enthalpy of Vaporization: 50.91 kJ/mol; (15)Boiling Point: 270.9 °C at 760 mmHg; (16)Vapour Pressure: 0.00666 mmHg at 25°C.

Preparation of Dimethyl furan-2,5-dicarboxylate: This chemical can be prepared by methanol and furan-2,5-dicarboxylic acid. The reaction will need reagent p-toluenesulfonic acid monohydrate. The reaction time is 3 hours with heating, and the yield is about 68%.  


 
Uses of Dimethyl furan-2,5-dicarboxylate: It can produce furan-2,5-dicarboxylic acid dihydrazide. This reaction will need reagent hydrazine hydrate, and the menstruum methanol. The reaction time is 2 hours with heating, and the yield is about 88%.   

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(OC)c1oc(C(=O)OC)cc1
(2)InChI: InChI=1/C8H8O5/c1-11-7(9)5-3-4-6(13-5)8(10)12-2/h3-4H,1-2H3
(3)InChIKey: UWQOPFRNDNVUOA-UHFFFAOYAK

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