sodium ethanolate

• ChemBase ID: 108964
• Molecular Formular: C2H5NaO
• Molecular Mass: 68.05027
• Monoisotopic Mass: 68.02380906
• SMILES: [Na+].CC[O-]
• Canonical SMILES: [O-]CC.[Na+]
• InChI: InChI=1S/C2H5O.Na/c1-2-3;/h2H2,1H3;/q-1;+1
• InChIKey: QDRKDTQENPPHOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium ethanolate
• IUPAC Traditional name: sodium ethoxide
• Synonyms: Sodium ethoxide; SODIUM ETHYLATE; Sodium ethoxide; Sodium ethylate; Sodium ethoxide solution; 乙醇钠; 乙氧钠; 乙醇钠 溶液

Database IDs

• CAS Number: 141-52-6
• EC Number: 205-487-5
• MDL Number: MFCD00012417
• Beilstein Number: 3593646
• Merck Index: 148613
• PubChem SID: 24886022; 24886021; 24849599; 24853819; 162094718
• PubChem CID: 2723922
• Chemspider ID: 8516
• Wikipedia Title: Sodium_ethoxide

CALCULATED PROPERTIES

• Acid pKa: 16.470615
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.1617691
• LogD (pH = 7.4): -0.1617691
• Log P: -0.1617691
• Molar Refractivity: 23.5602 cm^3
• Polarizability: 4.748913 Å^3
• Polar Surface Area: 23.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: miscible with ethanol and methanol; Reacts in water
• Apperance: white or yellowish powder ; hygroscopic
• Melting Point: >300°C; 260°C
• Flash Point: 20°C(68°F); 30 °C; 30°C(86°F); 48.2 °F; 86 °F; 9 °C
• Density: 0.868; 0.868 g/cm^3; 0.868 g/mL at 25 °C
• Refractive Index: 1.3875; n20/D 1.385; n20/D 1.386
• Vapor Pressure: <0.1 mmHg ( 20 °C)
• Vapor Density: 1.6 (vs air)
• pKa: 15.5

Safety Information

• Storage Warning: Air & Moisture Sensitive; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Highly flammable (F+); Nature polluting (N); Harmful (Xn)
• UN Number: 3206; 3274; UN3206; UN3274
• German water hazard class: 1
• Hazard Class: 3; 4.2
• Packing Group: 2; II
• Risk Statements: 11-14-20/21/22-34-51/53-68/20/21/22; 11-14-34; R:11-14-34
• Safety Statements: 16-26-36/37/39-45; 16-26-36/37/39-45-61; 7/8-16-26-30-36/37/39-43-45-60; 8-16-26-43-45; S:8-16-26-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

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• GHS Hazard statements: H225-H251-H314; H225-H251-H314-H371-H411; H225-H314; H251-H314; H251-H314-H318
• GHS Precautionary statements: P210-P235 + P410-P260-P273-P280-P305 + P351 + P338; P210-P235 + P410-P280-P305 + P351 + P338-P310; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P235 + P410-P280-P305 + P351 + P338-P310; P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3206 4.2/PG 2; UN 3274 3/PG 2
• Supplemental Hazard Statements: Reacts violently with water.

Product Information

• Purity: ≥95% (T); ≥95.0%; 21% w/w in ethanol; 95%; 96%
• Concentration: ~21% in denatured ethanol (T); 21 wt. % in ethanol
• Grade: SAJ first grade; technical
• Impurities: ~2% Na2CO3 and NaOH
• Linear Formula: CH3CH2ONa

DETAILS

MP Biomedicals - 05209376

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 71212

Caution
may discolor to brown on storage

Sigma Aldrich - 156248

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
5, 100, 500 g in steel can

Sigma Aldrich - 230553

Packaging
1 L in glass bottle
100, 500 mL in glass bottle

REFERENCES

• In reactions where the presence of excess ethanol is undesirable, the use of pre-formed solid sodium ethoxide is much more convenient and safer than preparation in situ from sodium metal. This applies to many literature condensation reactions which employ powdered sodium in, for example ether or toluene, where the difficulty and hazards of obtaining a satisfactory sodium dispersion can be considerable. Solid sodium ethoxide often gives superior results, with better control of exothermic reactions.
• Extensively used as a base for the generation of carbanions in a variety of alkylation and condensation reactions. Organic Syntheses examples of the use of solid sodium ethoxide include:
• Condensation of acetone with ethyl acetate: Org. Synth. Coll., 3, 17 (1955). Benzoylation of acetophenone with ethyl benzoate: Org. Synth. Coll., 3, 251 (1955). ɑ-Formylations with ethyl formate: Org. Synth. Coll., 3, 300 (1955); 4, 536 (1963). ɑ-Ethoxalylation of diethyl succinate with diethyl oxalate: Org. Synth. Coll., 5, 687 (1973).