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77-93-0

Basic Information
CAS No.: 77-93-0
Name: 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-triethyl ester
Molecular Structure:
Molecular Structure of 77-93-0 (1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-triethyl ester)
Formula: C12H20O7
Molecular Weight: 276.32
Synonyms: 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, triethyl ester (9CI);Citric acid, triethyl ester (6CI,7CI,8CI);Citroflex 2;Citroflex C 2;Citroflex EC;Citroflex SC 60;Citrofol A 1;Citrofol AI;Ethyl citrate;Eudraflex;Hydragen CAT;Morflex C 2;Morflex TEC;NSC 8907;
EINECS: 201-070-7
Density: 1.177 g/cm3
Melting Point: -46 °C
Boiling Point: 294 °C at 760 mmHg
Flash Point: 95.4 °C
Solubility: 5.7 g/100 mL (25 °C) in water
Appearance: clear liquid
Hazard Symbols: Xn
Risk Codes: 20
Safety: 24/25
Transport Information:
PSA: 99.13000
LogP: 0.18700
Synthetic route
64-17-5

ethanol

77-92-9

citric acid

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Stage #1: ethanol With dicyclohexyl-carbodiimide at 20℃; for 36h; Large scale;
Stage #2: citric acid at 35℃; for 6h; Temperature; Autoclave; Large scale;
96%
With sulfonated graphene In neat (no solvent) at 90℃; for 4h;94%
With boric acid; benzenesulfonic acid at 85 - 90℃; for 3h;93.26%
105-50-0

diethyl 1,3-acetonedicarboxylate

109-94-4

formic acid ethyl ester

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With potassium hydroxide
64-17-5

ethanol

199341-50-9

((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With sodium ethanolate Ambient temperature; Yield given;
64-17-5

ethanol

((S)-4-Ethoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With triethylamine Heating; Yield given;
105-50-0

diethyl 1,3-acetonedicarboxylate

109-94-4

formic acid ethyl ester

KOH

KOH

77-93-0

citric acid triethyl ester

109-94-4

formic acid ethyl ester

acetone-dicarboxylic acid-(1.3)-diethyl ester

acetone-dicarboxylic acid-(1.3)-diethyl ester

KOH

KOH

77-93-0

citric acid triethyl ester

10026-13-8, 874483-75-7

phosphorus pentachloride

77-92-9

citric acid

A

77-93-0

citric acid triethyl ester

B

aconitic acid chloride

aconitic acid chloride

Conditions
ConditionsYield
dann mit Alkohol;
75-03-6

ethyl iodide

citrate silver

citrate silver

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
at 100℃; in geschlossenem Rohr;
64-17-5

ethanol

77-92-9

citric acid

A

4552-00-5

ethyl citrate

B

101996-63-8

citric acid α,α'-diethyl ester

C

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Amberlyst 15 at 25 - 120℃; for 7 - 16h; Product distribution / selectivity;
144-16-1

5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / dimethoxypropane, Dowex 50WX4, MeOH / 24 h / Heating
2: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature
3: EtONa / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 85 percent / diethoxypropane, Dowex 50WX4, MeOH / 24 h / Heating
2: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature
3: Et3N / Heating
View Scheme
112535-39-4

(5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid diethyl ester

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature
2: Et3N / Heating
View Scheme
77862-72-7

(5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid dimethyl ester

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pig liver esterase, aq. phosphate buffer pH=7, aq. NaOH / 2 h / Ambient temperature
2: EtONa / Ambient temperature
View Scheme
67-56-1

methanol

77-89-4

triethyl O-acetylcitrate

75-64-9

tert-butylamine

A

1587-20-8

trimethyl citrate

B

77-93-0

citric acid triethyl ester

C

1242516-65-9

dimethyl 3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioate

D

1242516-64-8

3-(tertbutylcarbamoyl)-3-acetoxy-pentanedioic acid

Conditions
ConditionsYield
at 20℃;
64-17-5

ethanol

77-92-9

citric acid

A

4676-51-1

Diethyl 2-methylsuccinate

B

77-93-0

citric acid triethyl ester

Conditions
ConditionsYield
With hydrogen In water at 200℃; under 3000.3 Torr; for 6h;A 19 %Spectr.
B n/a
107-10-8

propylamine

77-93-0

citric acid triethyl ester

367493-05-8

2-hydroxy-N1,N2,N3-tripropylpropane-1,2,3-tricarboxamide

Conditions
ConditionsYield
In methanol at 20℃;96%
77-93-0

citric acid triethyl ester

109-73-9

N-butylamine

38328-55-1

N1,N2,N3-tributyl-2-hydroxypropane-1,2,3-tricarboxamide

Conditions
ConditionsYield
In methanol at 20℃;93%
77-93-0

citric acid triethyl ester

108-24-7

acetic anhydride

77-89-4

triethyl O-acetylcitrate

Conditions
ConditionsYield
With 4-(dimethylamino)pyridine hydrochloride at 110℃; for 8h;90%
sulfuric acid at 80℃; for 3h;88%
With H-type zeolite catalyst at 60 - 120℃; under 760.051 Torr; for 2.83333h; Reagent/catalyst; Sealed tube; Inert atmosphere;
unter kontinuierlicher Entfernung der entstehenden Essigsaeure;
77-93-0

citric acid triethyl ester

93-97-0

benzoic acid anhydride

145867-24-9

C19H24O8

Conditions
ConditionsYield
With 4-(dimethylamino)pyridine hydrochloride at 110℃; for 28h;88%
77-93-0

citric acid triethyl ester

302962-49-8

dasatanib

C22H26ClN7O2S*C12H20O7

Conditions
ConditionsYield
In methanol at 20℃; for 3h;86%
77-93-0

citric acid triethyl ester

18960-42-4

2-hydroxypropane-1,2,3-tricarbohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 6h; Reflux;85%
With ethanol; hydrazine hydrate
77-93-0

citric acid triethyl ester

101996-63-8

citric acid α,α'-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; chymotripsin; phosphate buffer pH=7 for 96h; Ambient temperature;85%
77-93-0

citric acid triethyl ester

920-46-7

Methacryloyl chloride

186351-92-8

C16H24O8

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine In toluene at 0 - 20℃; for 4h; Inert atmosphere;82%
added-triethylcitrate

added-triethylcitrate

60-29-7

diethyl ether

77-93-0

citric acid triethyl ester

78-81-9

isobutylamine

367493-06-9

N,N',N"-tri-iso-butylcitramide

Conditions
ConditionsYield
In methanol80.3%
77-93-0

citric acid triethyl ester

753-55-9

dimethyl aluminum fluoride

252270-77-2

[(C(CH2COOC2H5)2(COOC2H5)O)AlF(CH3)]2

Conditions
ConditionsYield
In toluene byproducts: CH4; N2-atmosphere; dropwise addn. of citrate ester to 1 equiv. Al-compd. at room temp., stirring for 24 h; crystn. (-20°C); further crop on concn. of mother liquor; elem. anal.;63%
60-29-7

diethyl ether

77-93-0

citric acid triethyl ester

38328-55-1

N1,N2,N3-tributyl-2-hydroxypropane-1,2,3-tricarboxamide

Conditions
ConditionsYield
With N-butylamine In methanol58%
60-29-7

diethyl ether

77-93-0

citric acid triethyl ester

367493-05-8

2-hydroxy-N1,N2,N3-tripropylpropane-1,2,3-tricarboxamide

Conditions
ConditionsYield
With propylamine In methanol55%
77-93-0

citric acid triethyl ester

6-(benzyloxy)-1,3-dimethyl-1,3,5-triazine-2,4(1H,3H)-dione

112031-19-3

triethyl 2-benzyloxy-1,2,3-propanetricarboxylate

Conditions
ConditionsYield
With trifluoroacetic acid In 1,4-dioxane at 50℃; for 11h; Molecular sieve; Inert atmosphere;55%
107-85-7

1-amino-3-methylbutane

60-29-7

diethyl ether

77-93-0

citric acid triethyl ester

367493-07-0

N,N',N''-triisopentyl citramide

Conditions
ConditionsYield
In methanol52.1%
5%MeOH

5%MeOH

77-93-0

citric acid triethyl ester

19958-02-2

3-Hydroxy-3,4-bis(ethoxycarbonyl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; acetic acid In methanol; ethanol; water38%
77-93-0

citric acid triethyl ester

81927-55-1

O-benzyl 2,2,2-trichloroacetimidate

112031-19-3

triethyl 2-benzyloxy-1,2,3-propanetricarboxylate

Conditions
ConditionsYield
trifluorormethanesulfonic acid In dichloromethane; cyclohexane for 2.5h; Ambient temperature;5%
77-93-0

citric acid triethyl ester

18852-51-2

sodium cyanoacetic acid ethyl ester

861310-20-5

1-cyano-butane-1,2,3,4-tetracarboxylic acid tetraethyl ester

Conditions
ConditionsYield
With ethanol
77-93-0

citric acid triethyl ester

18852-51-2

sodium cyanoacetic acid ethyl ester

1703-61-3

rac-4-oxocyclopentane-1,2-dicarboxylic acid

Conditions
ConditionsYield
With ethanol Verseifung des neben 1-Cyan-butan-tetracarbonsaeure-(1.2.3.4)-tetraaethylester entstehenden Produkts mit Schwefelsaeure;
77-93-0

citric acid triethyl ester

4552-01-6

citric acid β-ethyl ester

Conditions
ConditionsYield
Verseifung;
With sodium hydroxide; Petroleum ether
77-93-0

citric acid triethyl ester

19958-02-2

3-Hydroxy-3,4-bis(ethoxycarbonyl)butanoic acid

Conditions
ConditionsYield
With sodium hydroxide durch fraktionierte Verseifung;
With sodium hydroxide; Petroleum ether at 0℃;
77-93-0

citric acid triethyl ester

5349-99-5

Diethyl-3-(ethoxycarbonyl)pent-2-endioat

Conditions
ConditionsYield
With phosphorus trichloride Destillation des Reaktionsproduktes;
With phosphorus pentachloride Destillation des Reaktionsproduktes;
Multi-step reaction with 2 steps
1: 88 percent / H2SO4 / 3 h / 80 °C
2: 89 percent / 1.5 h / 275 °C
View Scheme
77-93-0

citric acid triethyl ester

sulfurous acid bis-(1,2-bis-ethoxycarbonyl-1-ethoxycarbonylmethyl-ethyl ester)

Conditions
ConditionsYield
With pyridine; thionyl chloride; diethyl ether at 10℃;
77-93-0

citric acid triethyl ester

(4-hydroxy-3,6-dioxo-hexahydro-pyridazin-4-yl)-acetic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate
77-93-0

citric acid triethyl ester

103-71-9

phenyl isocyanate

2-phenylcarbamoyloxy-propane-1,2,3-tricarboxylic acid triethyl ester

Conditions
ConditionsYield
at 130℃;
77-93-0

citric acid triethyl ester

75-36-5

acetyl chloride

77-89-4

triethyl O-acetylcitrate

77-93-0

citric acid triethyl ester

2524-64-3

chlorophosphoric acid diphenyl ester

102089-54-3

2-diphenoxyphosphoryloxy-propane-1,2,3-tricarboxylic acid triethyl ester

Conditions
ConditionsYield
With pyridine
67-56-1

methanol

77-93-0

citric acid triethyl ester

64670-05-9

lithium sodium dianion of methyl acetoacetate

107182-07-0

methyl 1,8-dihydroxy-6-(ethoxycarbonyl)-2-(methoxycarbonyl)-3-naphthylacetate

Conditions
ConditionsYield
With calcium acetate 1.) THF, 0 deg C, 2 h; 2.) reflux, 2 h; Yield given. Multistep reaction;
77-93-0

citric acid triethyl ester

105-45-3

acetoacetic acid methyl ester

107182-07-0

methyl 1,8-dihydroxy-6-(ethoxycarbonyl)-2-(methoxycarbonyl)-3-naphthylacetate

Conditions
ConditionsYield
With n-butyllithium; calcium acetate; sodium hydride 1.) THF, hexane, 1 h, room temperature, 2.) MeOH, 2 h, reflux; Yield given. Multistep reaction;
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    Triethyl citrate CAS:77-93-0

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  • Casno:

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    BLOOM TECH Advanced API/Technology support Triethyl citrate CAS 77-93-0

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Triethyl citrate is triethyl 2-hydroxypropane-1,2,3-tricarboxylate. With the CAS registry number 77-93-0, it is also named as 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester. The product's categories are Functional Materials; Hydroxycarboxylic Acid Esters (Plasticizer); Plasticizer; Amino Ester. It is clear liquid which is soluble in most organic solvents and insoluble in oils. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.49; (4)ACD/LogD (pH 7.4): 1.49; (5)ACD/BCF (pH 5.5): 8.02; (6)ACD/BCF (pH 7.4): 8.02; (7)ACD/KOC (pH 5.5): 154.52; (8)ACD/KOC (pH 7.4): 154.51; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 12; (12)Index of Refraction: 1.461; (13)Molar Refractivity: 64.46 cm3; (14)Molar Volume: 234.6 cm3; (15)Polarizability: 25.55×10-24 cm3; (16)Surface Tension: 41.5 dyne/cm; (17)Enthalpy of Vaporization: 61.91 kJ/mol; (18)Vapour Pressure: 0.000175 mmHg at 25°C; (19)Rotatable Bond Count: 11; (20)Exact Mass: 276.120903; (21)MonoIsotopic Mass: 276.120903; (22)Topological Polar Surface Area: 99.1; (23)Heavy Atom Count: 19; (24)Complexity: 304.

Preparation of Triethyl citrate: It can be obtained by esterification of citric acid and alcohol in the presence of sulfuric acid.

Uses of Triethyl citrate: It is mainly used as plasticizer of cellulose, vinyl and other thermoplastic resin. It is also used as solvent, flavoring agent and chelating agent. In addition, it can react with acetic acid anhydride to get 2-acetoxy-propane-1,2,3-tricarboxylic acid triethyl ester. This reaction needs catalytic agent sulfuric acid at temperature of 80 °C. The reaction time is 3 hours. The yield is 88%.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(CC(O)(CC(=O)OCC)C(=O)OCC)OCC
2. InChI:InChI=1/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 3500mg/kg (3500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Food and Cosmetics Toxicology. Vol. 17, Pg. 389, 1979.
guinea pig LD50 oral > 25mL/kg (25mL/kg)   German Offenlegungsschrift Patent Document. Vol. #2703360,
mouse LD50 intraperitoneal 1750mg/kg (1750mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: OTHER CHANGES
Journal of Pharmaceutical Sciences. Vol. 53, Pg. 774, 1964.
 
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 389, 1979.
rat LC50 inhalation 1300ppm/6H (1300ppm) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
"Industrial Hygiene and Toxicology," 2nd ed., Patty, F.A., ed., New York, John Wiley & Sons, Inc., 1958-63Vol. 2, Pg. 1892, 1963.
rat LD50 intraperitoneal 4gm/kg (4000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 214, 1985.
rat LD50 oral 5900mg/kg (5900mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 214, 1985.
rat LD50 subcutaneous 6600mg/kg (6600mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 214, 1985.