1,1,1-triethoxyethane

• ChemBase ID: 109101
• Molecular Formular: C8H18O3
• Molecular Mass: 162.22672
• Monoisotopic Mass: 162.12559444
• SMILES: CCOC(C)(OCC)OCC
• Canonical SMILES: CCOC(OCC)(OCC)C
• InChI: InChI=1S/C8H18O3/c1-5-9-8(4,10-6-2)11-7-3/h5-7H2,1-4H3
• InChIKey: NDQXKKFRNOPRDW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1,1-triethoxyethane
• IUPAC Traditional name: ethane, 1,1,1-triethoxy-; triethyl orthoacetate
• Synonyms: ETHYL ORTHOACETATE; 1,1,1-triethoxyethane; 1,1,1-Triethoxyethane; Triethyl orthoacetate; Ethyl orthoacetate; Orthoacetic acid triethyl ester; 1,1,1-三乙氧基乙烷; 原乙酸三乙酯; 原醋酸三乙酯

Database IDs

• CAS Number: 78-39-7
• EC Number: 201-112-4
• MDL Number: MFCD00009223
• Beilstein Number: 506201
• PubChem SID: 162094657; 24886849; 24900341
• PubChem CID: 66221

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.0645168
• LogD (pH = 7.4): 2.0645168
• Log P: 2.0645168
• Molar Refractivity: 44.4342 cm^3
• Polarizability: 17.554483 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 142 °C(lit.); 142-143°C
• Flash Point: 32 °C; 32°C(89°F); 89.6 °F
• Density: 0.885 g/mL at 25 °C(lit.); 0.887
• Refractive Index: 1.3970; n20/D 1.396; n20/D 1.396(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3272; UN1993
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3

Product Information

• Purity: ≥98.0% (GC); 97%; 98%
• Grade: purum
• Linear Formula: CH3C(OC2H5)3

DETAILS

Sigma Aldrich - T60402

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

REFERENCES

• Under mild acid catalysis, reacts with ethynyl alcohols to give allenic esters, which can be conjugated over alumina. For examples, see: Org. Synth. Coll., 8, 251 (1993):
  
• The products with allylic alcohols undergo Claisen allyl ether rearrangement, with addition of a 2-carbon unit and repositioning of the double bond: J. Am. Chem. Soc., 92, 741 (1970); Tetrahedron Lett., 21, 1285 (1980):
  
• Reaction with BF₃ etherate gives the moderately stable selective alkylating agent, methyl diethoxycarbenium tetrafluoroborate: Synth. Commun., 19, 2307 (1989). Compare Triethyl orthoformate, A13587.
• Reagent for facile esterification of sulfonic and carboxylic acids: Tetrahedron Lett., 34, 7355 (1993).
• For further examples, see: Org. Synth. Coll., 6, 584 (1988); 7, 164 (1990).