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105-58-8

Basic Information
CAS No.: 105-58-8
Name: Diethyl carbonate
Article Data: 305
Cas Database
Molecular Structure:
Molecular Structure of 105-58-8 (Diethyl carbonate)
Formula: C5H10O3
Molecular Weight: 118.133
Synonyms: Diatol;Diatol (carbonate);Ethyl carbonate;Ethyl carbonate((EtO)2CO);Eufin;H-DEC;NSC 8849;Carbonicacid, diethyl ester;
EINECS: 203-311-1
Density: 0.976 g/cm3
Melting Point: -43 °C
Boiling Point: 126.8 °C at 760 mmHg
Flash Point: 31.1 °C
Solubility: Negligible
Appearance: colourless liquid with a mild odour
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 23/24/25-36/37/38-10
Safety: 26-36-45-16-23
Transport Information: UN 2811 6.1/PG 2
PSA: 35.53000
LogP: 1.17940
Synthetic route
64-17-5

ethanol

1184-76-5

difluorodiiodomethane

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Substitution;99%
96-49-1

[1,3]-dioxolan-2-one

64-17-5

ethanol

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With Zn6Al2(OH)16NO3·nΗ2O at 83℃; for 6h; Reagent/catalyst; Time;99%
at 69.84℃; for 6h; Catalytic behavior; Reagent/catalyst;78.1%
With carbon dioxide at 160℃; under 4500.45 Torr; for 4h; Autoclave;40.5%
124-38-9

carbon dioxide

76040-13-6

di-n-octyl-diethoxy tin

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
at 120℃; for 4h; Industry scale; Autoclave;99%
108-32-7

1,2-propylene cyclic carbonate

titanium(IV) tetraethanolate

A

1450828-10-0

C7H16O4Ti

B

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
Heating;A 99%
B 86%
64-17-5

ethanol

616-38-6

carbonic acid dimethyl ester

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With aluminum oxide; Ce2O; zinc(II) oxide at 120℃; under 15001.5 Torr; for 1.5h;97.2%
With sodium methylate In methanol at 69 - 120℃; for 6h; Temperature; Reflux;92%
With tetraethylammonium nitrilotriacetate at 130℃; for 2h;54%
122-51-0

orthoformic acid triethyl ester

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0℃; for 2h;95%
With mercury(II) diacetate at 190℃; for 2h;72%
With di-tert-butyl peroxide In chlorobenzene at 130℃; for 5h; Product distribution; Rate constant;57 % Turnov.
2463-45-8

4-chloromethyl-[1,3]dioxolan-2-one

141-52-6

sodium ethanolate

A

1874-62-0

3-ethoxy-1,2-propanediol

B

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
In ethanol at 80℃; for 1h;A n/a
B 88%
108-32-7

1,2-propylene cyclic carbonate

titanium(IV) tetraethanolate

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
Heating;86%
19172-47-5

Lawessons reagent

78-09-1

orthocarbonic acid tetraethyl ester

A

72368-61-7

O-ethyl S-ethyl di(4-methoxyphenyl)thiodiphosphonate

B

88722-15-0

O,S-diethyl-(4-methoxyphenyl)phosphonodithioate

C

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
In benzene at 80℃;A 70%
B 82%
C n/a
1493-05-6

difluoro-nitro-methane

141-52-6

sodium ethanolate

A

sodium fluoride

B

7632-00-0

sodium nitrite

C

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
In ethanol; dichloromethane alkoxide soln. (EtOH) addn. to F2C(NO2)2 soln. (CH2Cl2) (molar ratio F2C(NO2)2:nucleophile=1:4), reacting (-10°C for 10-15 min), stirring (0°C for 1 h, then 20°C for 1 h); salts. ppt. sepn. (CH2Cl2 addn.); chem. and GLC anal.;A 81%
B 78%
C 7%
In ethanol; dichloromethane alkoxide soln. (EtOH) addn. to F2C(NO2)2 soln. (CH2Cl2) (molar ratio F2C(NO2)2:nucleophile 1:2, reacting (-10°C for 10-15 min), stirring(0°C for 1 h), reaction mixt. leaving overnight at -20°C; salts. ppt. sepn. (CH2Cl2 addn., cooling), ppt. treatment with boiling ethanol, NaNO2 pptn. from filtrate, aq. H2SO4 addn. to filtrate, org. layer sepn., aq. layer extn. (CH2Cl2), ext. drying (MgSO4), distn. lead to(EtO)2CO; chem. and GLC anal.;A 48%
B 62%
C 12%
In ethanol; dichloromethane alkoxide soln. (EtOH) addn. to F2C(NO2)2 soln. (CH2Cl2) (molar ratio F2C(NO2)2:nucleophile=1:1), reacting (-10°C for 10-15 min), stirring (0°C for 1 h, then 20°C for 1 h); salts. ppt. sepn. (CH2Cl2 addn.); chem. and GLC anal.;A 18%
B 26%
C 9%
In ethanol; N,N-dimethyl-formamide alkoxide soln. (EtOH) addn. to F2C(NO2)2 soln. (DMF) (molar ratio F2C(NO2)2:nucleophile=1:2), reacting (-10°C for 10-15 min), stirring (0°C for 1 h); salts. ppt. sepn. (CH2Cl2 addn.); chem. and GLC anal.;
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Consensus Reports

Diethyl carbonate (105-58-8) Market Research Report 2009

Specification

1. Introduction of Diethyl carbonate
The Diethyl carbonate is an organic compound with the CAS registry number of 105-58-8, it is also named as carbonic acid, diethyl ester. The product's categories are Pharmaceutical Intermediates; Organics; Carbonates; Others; Protecting and Derivatizing Reagents; Protection and Derivatization; Carbonates Materials Science; Alternative Energy; Carbonyl Compounds; Electrolytes; Organic Building Blocks; Electrolytes Protection and Derivatization; Materials Science. Besides, it is a colourless liquid with a mild odour, which should be stored in a cool and ventilated place. It is mainly used as a solvent for cellulose ethers, nitro cellulose, natural and synthetic resin. And it is also used for the synthesis of phenobarbital, pyrethrum esters.

2. Properties of Diethyl carbonate
Physical properties about Diethyl carbonate are: (1)ACD/LogP: 1.21; (2)ACD/LogD (pH 5.5): 1.21; (3)ACD/LogD (pH 7.4): 1.21; (4)ACD/BCF (pH 5.5): 4.89; (5)ACD/BCF (pH 7.4): 4.89; (6)ACD/KOC (pH 5.5): 108.45; (7)ACD/KOC (pH 7.4): 108.45; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 35.53 Å2; (11)Index of Refraction: 1.391; (12)Molar Refractivity: 28.73 cm3; (13)Molar Volume: 120.9 cm3; (14)Polarizability: 11.39×10-24cm3; (15)Surface Tension: 26.9 dyne/cm; (16)Density: 0.976 g/cm3; (17)Flash Point: 31.1 °C; (18)Enthalpy of Vaporization: 36.46 kJ/mol; (19)Boiling Point: 126.8 °C at 760 mmHg; (20)Vapour Pressure: 11.5 mmHg at 25°C.

3. Structure Descriptors of Diethyl carbonate
(1)SMILES: O=C(OCC)OCC
(2)InChI: InChI=1/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3
(3)InChIKey: OIFBSDVPJOWBCH-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3
(5)Std. InChIKey: OIFBSDVPJOWBCH-UHFFFAOYSA-N

4. Toxicity of Diethyl carbonate

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 subcutaneous 8500mg/kg (8500mg/kg)   Compilation of LD50 Values of New Drugs.
rat LDLo oral 15gm/kg (15000mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 52, 1974.

5. Safety Information of Diethyl carbonate
Hazard Symbols:ToxicT;IrritantXi
Risk Codes:
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R10:Flammable.
Safety Description:
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 the label whenever possible.) 
S16:Keep away from sources of ignition. 
S23:Do not breathe vapour.

6. Preparation of Diethyl carbonate
Diethyl carbonate can be prepared by 1,1-diethoxy-ethene. This reaction will need reagent O3 and solvent pentane. The reaction  temperature is 0 °C. The yield is about 59%.



7. Use of Diethyl carbonate
Diethyl carbonate can be used to produce 3-ethyl-4-methyl-5-phenyl-3H-oxazol-2-one at temperature of 180 °C. It will need reagent K2CO3 with reaction time of 330 min. The yield is about 35%.



8. Other details of Diethyl carbonate
When you are using diethyl carbonate, please be cautious about it as the following:
It is flammable and toxic by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, Diethyl carbonate is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).