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1609-47-8

Basic Information
CAS No.: 1609-47-8
Name: Diethyl pyrocarbonate
Article Data: 20
Molecular Structure:
Molecular Structure of 1609-47-8 (Diethyl pyrocarbonate)
Formula: C6H10O5
Molecular Weight: 162.142
Synonyms: Dicarbonicacid, diethyl ester (9CI);Formic acid, oxydi-, diethyl ester (8CI);Pyrocarbonic acid diethyl ester (6CI);Baycovin;DEPC;Dekapex;Diethyldicarbonate;Diethyl oxydiformate;Piref;Ue 5908;carbonic acid, ethoxycarbonyl ethyl ester;Dicarbonic acid diethyl ester;Oxydiformic acid diethyl ester;
EINECS: 216-542-8
Density: 1.15 g/cm3
Melting Point: 69℃
Boiling Point: 201.3 °C at 760 mmHg
Flash Point: 69.4 °C
Solubility: slow decomposition in water
Appearance: colorless liquid
Hazard Symbols: HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 26-36-37/39
Transport Information: UN 2810
PSA: 61.83000
LogP: 1.31600
Synthetic route
541-41-3

chloroformic acid ethyl ester

1609-47-8

diethyl dicarbonate

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at -10℃; for 1h;93%
67-66-3

chloroform

541-41-3

chloroformic acid ethyl ester

diluted KOH

diluted KOH

A

1609-47-8

diethyl dicarbonate

B

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
oder anstatt Emetin mit tertiaeren Basen,entsteht noch das N-Carbaethoxy-Derivat der betreffenden tertiaeren Base;
541-41-3

chloroformic acid ethyl ester

emetine hydrochloride

emetine hydrochloride

1609-47-8

diethyl dicarbonate

Conditions
ConditionsYield
With potassium hydroxide; chloroform
With chloroform; 2,3-Dimethylaniline
With chloroform mit anderen tertiaeren Basen;
541-41-3

chloroformic acid ethyl ester

potassium-salt of carbonic acid monoethyl ester

potassium-salt of carbonic acid monoethyl ester

1609-47-8

diethyl dicarbonate

Conditions
ConditionsYield
With toluene
64-17-5

ethanol

24424-99-5

di-tert-butyl dicarbonate

A

27945-07-9

tert-butyl ethyl carbonate

B

19935-69-4

Ethyl-tert-butylpyrocarbonat

C

1609-47-8

diethyl dicarbonate

D

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; Product distribution; Further Variations:; Solvents; reaction times; Condensation;
5536-61-8

sodium methacrylate

541-41-3

chloroformic acid ethyl ester

A

760-93-0

methacryloyl anhydride

B

1609-47-8

diethyl dicarbonate

C

21982-91-2

carboethoxymethacrylic anhydride

D

105-58-8

Diethyl carbonate

541-41-3

chloroformic acid ethyl ester

124-30-1

1-aminooctadecane

1609-47-8

diethyl dicarbonate

Conditions
ConditionsYield
With sodium hydroxide; magnesium sulfate; PEG 15 stearamine In water
50-24-8

prednisolon

1609-47-8

diethyl dicarbonate

Prednisolone 21-ethylcarbonate

Conditions
ConditionsYield
In acetone for 0.5h; Heating;100%
50-23-7

HYDROCORTISONE

1609-47-8

diethyl dicarbonate

Hydrocortisone-21-ethyl carbonate

Conditions
ConditionsYield
In ethanol for 0.5h; Heating;100%
50-28-2

estradiol

1609-47-8

diethyl dicarbonate

105660-13-7

17β-Estradiol-bis-ethyl carbonate

Conditions
ConditionsYield
for 0.5h; Heating;100%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Diethyl dicarbonate, with the CAS registry number 1609-47-8 and EINECS registry number 216-542-8, has the IUPAC name of ethoxycarbonyl ethyl carbonate. It is a kind of moisture sensitive liquid, and should be stored at 2-8°C. And the molecular formula of this chemical is C6H10O5.

The physical properties of Diethyl dicarbonate are as following: (1)ACD/LogP: 1.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.48; (4)ACD/LogD (pH 7.4): 1.48; (5)ACD/BCF (pH 5.5): 7.89; (6)ACD/BCF (pH 7.4): 7.89; (7)ACD/KOC (pH 5.5): 152.68; (8)ACD/KOC (pH 7.4): 152.68; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 61.83 Å2; (13)Index of Refraction: 1.413; (14)Molar Refractivity: 35.14 cm3; (15)Molar Volume: 140.9 cm3; (16)Polarizability: 13.93×10-24cm3; (17)Surface Tension: 33.9 dyne/cm; (18)Density: 1.15 g/cm3; (19)Flash Point: 69.4 °C; (20)Enthalpy of Vaporization: 43.75 kJ/mol; (21)Boiling Point: 201.3 °C at 760 mmHg; (22)Vapour Pressure: 0.31 mmHg at 25°C.

Uses of Diethyl dicarbonate: It can react with 2,2-dimethyl-2,5-dihydro-thiazole to produce 2,2-dimethyl-thiazole-3-carboxylic acid ethyl ester. This reaction will need reagent Pr3N, and the solvent toluene. The reaction time is 144 hours with heating, and the yield is about 90%.

Diethyl dicarbonate can react with 2,2-dimethyl-2,5-dihydro-thiazole to produce 2,2-dimethyl-thiazole-3-carboxylic acid ethyl ester

 

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting 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)OC(=O)OCC
(2)InChI: InChI=1/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3
(3)InChIKey: FFYPMLJYZAEMQB-UHFFFAOYAU

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 100mg/kg (100mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 52, 1974.
dog LD50 oral 500mg/kg (500mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 52, 1974.
guinea pig LCLo inhalation 10ppm/1H (10ppm) LUNGS, THORAX, OR RESPIRATION: DYSPNEA FAO Nutrition Meetings Report Series. Vol. 51A, Pg. 67, 1972.
mouse LCLo inhalation 10ppm/1H (10ppm) LUNGS, THORAX, OR RESPIRATION: DYSPNEA FAO Nutrition Meetings Report Series. Vol. 51A, Pg. 67, 1972.
mouse LD50 oral 1558mg/kg (1558mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 52, 1974.
rabbit LCLo inhalation 10ppm/1H (10ppm) LUNGS, THORAX, OR RESPIRATION: DYSPNEA FAO Nutrition Meetings Report Series. Vol. 51A, Pg. 67, 1972.
rabbit LD50 oral 500mg/kg (500mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 52, 1974.
rat LCLo inhalation 10gm/m3/1H (10000mg/m3)   Zeitschrift fuer Lebensmittel-Untersuchung und-Forschung. Vol. 114, Pg. 292, 1961.
rat LD50 intraperitoneal 47mg/kg (47mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 52, 1974.
rat LD50 oral 850mg/kg (850mg/kg)   FAO Nutrition Meetings Report Series. Vol. 51A, Pg. 67, 1972.