141-52-6

Basic information

• Product Name: Sodium ethoxide
• Synonyms: Sodium ethoxide 95%;Sodium ethoxide 96%;Sodium ethoxide solution;sodium ethylate solution;Sodiumethoxideinethanol;SODIUM ETHYLATE SOLUTION, ~21% IN ETHYL ALCOHOL, DENAT.;SODIUM ETHOXIDE, 21 WT. % SOLUTION IN DE NATURED ETHYL ALCOHOL;Sodium ethoxide, 21% in ethanol
• CAS NO: 141-52-6
• Molecular Formula: C₂H₅NaO
• Molecular Weight: 68.05
• EINECS: 205-487-5
• Product Categories: Classes of Metal Compounds;Na (Sodium) Compounds (excluding simple sodium salts);Typical Metal Compounds;metal alkoxide;Organics
• Mol File: 141-52-6.mol
• Article Data: 169

Chemical Properties

• Melting Point: 260 °C
• Boiling Point: 91°C
• Flash Point: 48 °F
• Appearance: Yellow to brown/Liquid
• Density: 0.868 g/mL at 25 °C
• Vapor Density: 1.6 (vs air)
• Vapor Pressure: <0.1 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.386
• Storage Temp.: Store at R.T.
• Solubility: Soluble in ethanol and methanol.
• Water Solubility: Miscible
• Sensitive: Moisture Sensitive
• Stability: Reacts violently with acids, water. Incompatible with chlorinated solvents, moisture. Absorbs carbon dioxide from the air. Highl
• Merck: 14,8539
• BRN: 3593646
• CAS DataBase Reference: Sodium ethoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium ethoxide(141-52-6)
• EPA Substance Registry System: Sodium ethoxide(141-52-6)

Safety Data

• Hazard Codes: F,C,Xi,N
• Statements: 11-14-34-36/37/38-68/20/21/22-51/53-20/21/22
• Safety Statements: 8-16-26-43-45-36/37/39-36-61
• RIDADR: UN 3274 3/PG 2
• WGK Germany: 1
• F: 3-8-10-23
• TSCA: Yes
• HazardClass: 4.2
• PackingGroup: II
• Hazardous Substances Data: 141-52-6(Hazardous Substances Data)

Usage

Hazard

As for caustic soda, ethanol. Sodium hydroxide is formed when sodium ethylate is exposed to moisture.

Purification Methods

It is a hygroscopic powder which should be stored under N2 in a cool place. A likely impurity is EtOH which can be removed by warming at 60-80o under high vacuum. It is hydrolysed by H2O to yield NaOH and EtOH. Other impurities, if kept in air for long periods are NaOH and Na2CO3. In this case the powder cannot be used if these impurities affect the reactivity, and a fresh sample should be acquired [IR: Seubold J Org Chem 21 156 1956]. [Beilstein 1 H 311, 1 IV 1289.]

Definition

ChEBI: An organic monosodium salt that has ethoxide as the counterion.

Preparation

Sodium ethoxide is prepared by reacting sodium with absolute ethanol: 2Na + 2C2H5OH → 2C2H5ONa + H2 Sodium in small quantities is added to absolute alcohol at 10°C. The temperature is raised to warming (to about 38°C). The mixture is cooled again and sodium and absolute alcohol are added gradually followed by careful warming. The process is repeated to obtain a sufficient yield of the p

Chemical Properties

White powder, sometimes having brownish tinge; readily hydrolyzes to alcohol and sodium hydroxide.

Uses

Sodium ethoxide is used in organic synthesis for condensation reactions. It also is a catalyst in many organic reactions.

Physical properties

White or yellowish powder; hygroscopic; darkens and decomposes on exposure to air; decomposes in water forming sodium hydroxide and ethanol; dissolves in absolute ethanol.

InChI:InChI=1/C2H6O.Na/c1-2-3;/h3H,2H2,1H3;/q;+1

Synthetic route

ethanol (64-17-5) → sodium ethanolate (141-52-6)

Conditions	Yield
With sodium at 25 - 30℃; under 75.0075 Torr; for 2h; Pressure; Temperature; Large scale;	97.62%
With sodium iodide at 28℃; Mechanism; Rate constant; Irradiation; investigated by a time-of-flight mass spectrometer;
at 200℃; Leiten in eine Suspension von NaOH in Paraffinoel;

phenythoin (57-41-0) + ethyl bromoacetate (105-36-2) → ethyl 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate (976-85-2) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol	A 96% B n/a

oxalic acid diethyl ester (95-92-1) → spiro [4H-1-benzopyran-4,2'-pyrrolidine]3'-carboxylic acid + sodium ethanolate (141-52-6)

Conditions	Yield
With sodium In ethanol	A 84% B n/a

3-cyclohexene-1-chloromethane + diethyl malonate (105-53-3) → sodium ethanolate (141-52-6)

Conditions	Yield
In diethyl ether; ethanol; water	48%

diethyl ether (60-29-7) + isopentyl sodium (2875-34-5) → sodium ethanolate (141-52-6)

diethyl ether (60-29-7) + ethyl sodium (676-54-0) → ethane (74-84-0) + ethene (74-85-1) + sodium ethanolate (141-52-6)

diethyl ether (60-29-7) + ethyl sodium (676-54-0) → sodium ethanolate (141-52-6)

pentaethoxyethane (58995-69-0) + ethyl sodium (676-54-0) → ethane (74-84-0) + tetraethoxyethene (40923-93-1) + sodium ethanolate (141-52-6)

(+/-)-erythro-5-oxo-2.3.5-triphenyl-valeric acid ethyl ester (62071-28-7) + 1,3-diphenyl-propen-3-one (614-47-1) + benzene (71-43-2) → 3-benzoyl-1,2,4,6-tetraphenyl-cyclohex-3-enecarboxylic acid ethyl ester (859176-77-5) + sodium ethanolate (141-52-6)

C10H12N3O8(1-) → 2,4,6-trinitro-phenetole (4732-14-3) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol at 25℃; Equilibrium constant; measured by UV spectroscopy;

C9H10N3O8(1-) → sodium ethanolate (141-52-6) + 1-methoxy-2,4,6-trinitrobenzene (606-35-9)

Conditions	Yield
In ethanol at 25℃; Equilibrium constant; measured by UV spectroscopy;

C11H14N3O8(1-) → n-propyl-2,4,6-trinitrophenyl ether (10242-24-7) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol at 25℃; Equilibrium constant; measured by UV spectroscopy;

C11H14N3O8(1-) → 2,4,6-trinitrophenyl isopropyl ether (10242-23-6) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol at 25℃; Equilibrium constant; measured by UV spectroscopy;

C16H11N6O13(1-) → 2,2',4.4',6,6'-hexanitrostilbene (19138-90-0) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol; dimethyl sulfoxide at 25℃; Rate constant; Equilibrium constant; sodium perchlorate;

C16H11N6O13(1-) → 2,2',4.4',6,6'-hexanitrostilbene (19138-90-0) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol; dimethyl sulfoxide at 25℃; Rate constant; Equilibrium constant;

C18H16N6O14(2-) → 2,2',4.4',6,6'-hexanitrostilbene (19138-90-0) + sodium ethanolate (141-52-6)

Conditions	Yield
In ethanol; dimethyl sulfoxide at 25℃; Rate constant; Equilibrium constant; sodium perchlorate;

2-phenylmethylsulfonylpyridine-1-oxide (14694-58-7) + sodium ethanolate (141-52-6) → 2-ethoxylpyridine N-oxide (3445-09-8) + C7H7O2S(1-)*Na(1+)

Conditions	Yield
In ethanol for 0.25h; Heating;	A n/a B 100%

2-(Propane-2-sulfonyl)-pyridine 1-oxide (62381-86-6) + sodium ethanolate (141-52-6) → 2-ethoxylpyridine N-oxide (3445-09-8) + C3H7O2S(1-)*Na(1+)

Conditions	Yield
In ethanol for 0.25h; Heating;	A n/a B 100%

N-benzoyl-L-glutamic acid α-methyl ester (124126-80-3) + sodium ethanolate (141-52-6) → N-benzoyl-L-glutamic acid α-ethyl ester (23262-03-5)

Conditions	Yield
In ethanol for 1.5h; Ambient temperature;	100%

sodium ethanolate (141-52-6) + 2-Methanesulfonyl-pyridine 1-oxide (75853-86-0) → 2-ethoxylpyridine N-oxide (3445-09-8) + CH3O2S(1-)*Na(1+)

Conditions	Yield
In ethanol for 0.166667h; Heating;	A 95% B 100%

sodium ethanolate (141-52-6) + 2-(2-Methyl-propane-2-sulfonyl)-pyridine 1-oxide (109277-65-8) → 2-ethoxylpyridine N-oxide (3445-09-8) + C4H9O2S(1-)*Na(1+)

Conditions	Yield
In ethanol for 0.25h; Heating;	A n/a B 100%

sodium ethanolate (141-52-6) + exo-7-carbethoxy-endo-9-methyl-2-oxabicyclo<4.3.1>decan-3-one (82979-09-7) → (1S,2S,4R,5S)-2-(2-Ethoxycarbonyl-ethyl)-4-hydroxy-5-methyl-cyclohexanecarboxylic acid ethyl ester (82979-10-0)

Conditions	Yield
In ethanol at 0℃; for 0.5h;	100%

sodium ethanolate (141-52-6) + 2-(Octane-1-sulfonyl)-pyridine 1-oxide (109277-64-7) → 2-ethoxylpyridine N-oxide (3445-09-8) + C8H17O2S(1-)*Na(1+)

Conditions	Yield
In ethanol for 0.5h; Heating;	A n/a B 100%

sodium ethanolate (141-52-6) + (3-hexadecyloxysulfonyl-propyl)-trimethyl-ammonium; perchlorate → ethyl hexadecyl ether (13933-61-4)

Conditions	Yield
In ethanol at 25℃; for 48h;	100%

sodium ethanolate (141-52-6) + 2-(4-benzyl-1-piperazinyl)-4-chloro-5,6,7,8-tetrahydroquinazoline (79051-10-8) → 2-(4-Benzyl-piperazin-1-yl)-4-ethoxy-5,6,7,8-tetrahydro-quinazoline (81532-51-6)

Conditions	Yield
In ethanol for 6h; Heating;	100%

sodium ethanolate (141-52-6) + 2,4,6-trichloro-1H-1,5,2λ5-diazaphosphorine 2-oxide (155932-10-8) → 4,6-dichloro-2-ethoxy-1H-1,5,2λ5-diazaphosphorine 2-oxide

Conditions	Yield
In benzene for 0.5h; Ambient temperature;	100%

sodium ethanolate (141-52-6) + 2-(p-methoxyphenyl)-1,3-diphenylbenzothiophenium perchlorate → C29H26O2S

Conditions	Yield
In ethanol for 12h; Heating;	100%

sodium ethanolate (141-52-6) + [6-Hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-yl]methyl bromide (187806-29-7) → 5-ethyloxymethyl-γ-tocopherol (19741-08-3)

Conditions	Yield
In ethanol; hexane at 0℃; for 1h;	100%

sodium ethanolate (141-52-6) + (+/-)-5,6-dimethyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide → sodium 3,4-dimethyl-6-ethoxymethyl-3-cyclohexene-1-sulfonate

Conditions	Yield
Ambient temperature;	100%
for 4h; Ambient temperature;	100%

sodium ethanolate (141-52-6) + (+/-)-endo-4,3-oxathiatricyclo<5.2.1.02,6>deca-8-ene 3,3-dioxide → sodium 3-ethoxymethylbicyclo<2.2.1>hept-5-ene-2-sulfonate

Conditions	Yield
Ambient temperature;	100%
for 4h; Ambient temperature;	100%

sodium ethanolate (141-52-6) + ethylene dibromide (106-93-4) + para-thiocresol (106-45-6) → (2-ethoxyethyl)-para-thiocresol (57023-03-7)

Conditions	Yield
Stage #1: para-thiocresol With sodium ethanolate In ethanol at 20℃; Metallation; Stage #2: ethylene dibromide In ethanol at 20℃; Alkylation; Stage #3: sodium ethanolate In ethanol Substitution; Heating;	100%

sodium ethanolate (141-52-6) + methyldibromobismuth(III) (60458-17-5) → methyldiethoxybismutane (60458-07-3)

Conditions	Yield
In ethanol 2 h, 20°C;	100%

cis-3-phenyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester + sodium ethanolate (141-52-6) → trans-3-phenyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Conditions	Yield
In ethanol for 4h; Heating / reflux;	100%

2,2,2-trichloro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanone (1346672-30-7) + sodium ethanolate (141-52-6) → 4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester (65880-18-4)

Conditions	Yield
In ethanol at 20℃; for 1h; Inert atmosphere;	100%
With ethanol at 20℃; for 1h; Inert atmosphere;	100%
In ethanol at 20℃; for 1h; Inert atmosphere;	100%

1-(4-fluoro-phenyl)-4-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid[4-(2-phenyl-furo[3,2-b]pyridin-7-yloxy)-phenyl]-amide (1360906-01-9) + sodium ethanolate (141-52-6) → 4-ethoxy-1-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid[4-(2-phenyl-furo[3,2-b]pyridin-7-yloxy)-phenyl]-amide (1360906-05-3)

Conditions	Yield
With ethanol In tetrahydrofuran at 20℃; for 1h; Sealed tube; Inert atmosphere;	100%

ethanol (64-17-5) + ethyl 7-methyl-2-(methylsulfanyl)-4-oxo-3-(2-oxo-2-phenylethyl)-5-(2,2,2-trifluoroethoxy)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-6-carboxylate (1269119-25-6) + sodium ethanolate (141-52-6) → ethyl 2-ethoxy-7-methyl-4-oxo-3-(2-oxo-2-phenylethyl)-5-(2,2,2-trifluoroethoxy)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-6-carboxylate (1269119-28-9)

Conditions	Yield
In tetrahydrofuran at 10 - 35℃; for 4h;	100%

C24H29F2NPPd + sodium ethanolate (141-52-6) → C26H33FNOPPd

Conditions	Yield
In ethanol; benzene at 20℃; for 0.1h;	100%

ethanol (64-17-5) + sodium ethanolate (141-52-6) + methanesulfonic acid 3-nitrobenzylester → 1-(ethoxymethyl)-3-nitrobenzene (80171-39-7)

Conditions	Yield
for 17h; Reflux; Inert atmosphere;	100%

5-ethyl-1,3-diphenylimidazo[4,5-b]pyrazin-3-ium tetrafluoroborate + sodium ethanolate (141-52-6) → 2-ethoxy-5-ethyl-1,3-diphenyl-2H-imidazo[4,5-b]pyrazine

Conditions	Yield
In ethanol for 0.75h; Inert atmosphere; Cooling with ice;	100%

3-(3,5-dimethyiphenyl)-1-phenyl-5-(trifluoromethoxy)benzimidazol-3-ium chloride + sodium ethanolate (141-52-6) → 3-(3,5-dimethylphenyl)-2-ethoxy-1-phenyl-5-(trifluoromethoxy)-2H-benzimidazole

Conditions	Yield
In n-heptane for 0.5h; Inert atmosphere;	100%

2,4-dinitrobromobenzene (584-48-5) + sodium ethanolate (141-52-6) → 2,4-dinitro-1-ethoxybenzene (610-54-8)

Conditions	Yield
In ethanol at 25℃; Kinetics;	100%

1-iodo-2,4-dinitrobenzene (709-49-9) + sodium ethanolate (141-52-6) → 2,4-dinitro-1-ethoxybenzene (610-54-8)

Conditions	Yield
In ethanol at 25℃; Kinetics;	100%

5-bromo-2-chloro-3-methylpyridine (29241-60-9) + sodium ethanolate (141-52-6) → 5-bromo-2-ethoxy-3-methylpyridine

Conditions	Yield
Stage #1: 5-bromo-2-chloro-3-methylpyridine With sodium hydride In tetrahydrofuran; ethanol; mineral oil at 20℃; for 72.5h; Stage #2: sodium ethanolate In tetrahydrofuran; ethanol; mineral oil Reflux;	100%

1-azido-3-fluoro-2-nitrobenzene (874279-84-2) + sodium ethanolate (141-52-6) → C8H8N2O3

Conditions	Yield
Stage #1: 1-azido-3-fluoro-2-nitrobenzene In toluene for 5h; Reflux; Stage #2: sodium ethanolate In ethanol; toluene at 20℃; for 0.5h;	100%

3,5-difluoro-2-nitrophenylazide + sodium ethanolate (141-52-6) → 4,6-diethoxybenzofuroxan

Conditions	Yield
Stage #1: 3,5-difluoro-2-nitrophenylazide In toluene for 15h; Reflux; Stage #2: sodium ethanolate In ethanol; toluene at 20℃; for 0.5h;	100%

5-bromo-2-chloro-3-nitropyridine (67443-38-3) + sodium ethanolate (141-52-6) → 5-bromo-2-ethoxy-3-nitropyridine (886372-76-5)

Conditions	Yield
In ethanol at 75℃; for 1h;	100%
In ethanol at 80℃; for 1h;	57.67%

Upstream product

• 98-85-1 DL-1-Phenethylalcohol 
• 64-17-5 Etanol 

Downstream Products

• 488-93-7 3-Furoic acid 
• 20461-60-3 2,4-DIETHOXYPYRIMIDINE 
• 83657-17-4 UNICONAZOLE 
• 26717-67-9 Dimethyl ethylmalonate 
• 56442-17-2 4-(4-FLUOROBENZYLOXY)BENZALDEHYDE 
• 7803-49-8 HYDROXYLAMINE 
• 97780-06-8 Ethametsulfuron-methyl 
• 37555-99-0 2-ETHOXY-MALONIC ACID DIETHYL ESTER 
• 26377-17-3 ETHYL ISONICOTINOYLACETATE 
• 2847-30-5 2-Methoxy-3-methylpyrazine 
• 56752-40-0 2-METHOXYPROPANDIOIC ACID ETHYL METHYL ESTER 
• 700-79-8 Quinazoline, 2-methyl- (6CI,7CI,8CI,9CI) 
• 21187-98-4 Gliclazide 
• 77-83-8 Ethyl 3-methyl-3-phenylglycidate 
• 3731-16-6 3-CARBETHOXY-2-PIPERIDONE 
• 7459-46-3 TRIETHYL 1,1,2-ETHANETRICARBOXYLATE 
• 2922-41-0 P-AMINO-DL-PHENYLALANINE 
• 2031-67-6 Methyltriethoxysilane 
• 396-01-0 2,4,7-Triamino-6-phenylpteridine 
• 64039-56-1 2-(2-MORPHOLIN-4-YLETHOXY)ANILINE 
• 4415-82-1 Cyclobutanemethanol 
• 110-41-8 2-METHYLUNDECANAL 
• 79286-79-6 3-Aminopyrrolidine 
• 5398-08-3 Diethyl isoamylmalonate 
• 9005-64-5 Tween 20 
• 133-08-4 Diethyl butylmalonate 
• 7492-67-3 FEMA 2310 
• 6065-63-0 Diethyl dipropylmalonate 
• 19387-84-9 4-TERT-BUTYL-2,6-DIMETHYL BENZYL ACETATE 
• 9005-66-7 Polyoxyethylene sorbitan monopalmitate 
• 31329-57-4 NAFRONYL 
• 56-09-7 2-Amino-4,6-dihydroxypyrimidine 
• 17216-62-5 DIETHYL 2-(2-CYANOETHYL)MALONATE 
• 9005-65-6 Tween 80 
• 63935-26-2 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid 
• 15679-19-3 2-Ethoxythiazole 

Recommend Products

• 93-86-7  2-(2,5-dimethylphenoxy)ethan-1-ol 
• 75-21-8  oxirane 
• 95-87-4  2,5-Dimethylphenol 
• 313655-45-7  2-(2-cyanophenoxy)ethyl alcohol 
• 611-20-1  salicylonitrile 
• 64-17-5  ethanol 
• 16365-27-8  2-(4-nitrophenoxy)ethanol 
• 100-02-7  4-nitro-phenol 
• 56949-66-7  1-(2-hydroxyethyl)-2-methoxy-4-(2-propenyl)benzene 
• 97-53-0  4-allylguaiacol 
• 67548-69-0  2-mesityloxy-ethanol 
• 527-60-6  Mesitol 
• 16365-26-7  2-(3-nitrophenoxy)ethanol 
• 554-84-7  meta-nitrophenol 

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