(diethoxymethoxy)ethane

• ChemBase ID: 104743
• Molecular Formular: C7H16O3
• Molecular Mass: 148.20014
• Monoisotopic Mass: 148.10994437
• SMILES: CCOC(OCC)OCC
• Canonical SMILES: CCOC(OCC)OCC
• InChI: InChI=1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3
• InChIKey: GKASDNZWUGIAMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (diethoxymethoxy)ethane
• IUPAC Traditional name: triethyl orthoformate
• Synonyms: 1,1,1-Triethoxymethane; Triethyl orthoformate; ETHYL ORTHOFORMATE; TRIETHYL ORTHOFORMATE; Triethoxymethane; Ethyl orthoformate; triethoxymethane; Orthoformic acid triethyl ester; 1,1,1-三乙氧基甲烷; 原甲酸三乙酯

Database IDs

• CAS Number: 122-51-0
• EC Number: 204-550-4
• MDL Number: MFCD00009230
• Beilstein Number: 605384
• Merck Index: 146884
• PubChem SID: 24900342; 162092273; 24886840; 24858320
• PubChem CID: 31214
• Wikipedia Title: Triethyl_orthoformate

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8138654
• LogD (pH = 7.4): 1.8138654
• Log P: 1.8138654
• Molar Refractivity: 39.5842 cm^3
• Polarizability: 15.720697 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -61°C; -61°C; -76 °C(lit.); -76°C
• Boiling Point: 144°C; 144-146°C; 146 °C(lit.); 146°C
• Flash Point: 30°C(86°F); 35 °C; 95 °F
• Density: 0.891; 0.891 g/mL; 0.891 g/mL at 25 °C(lit.); 0.9 g/ml; 0.90 g/ml
• Refractive Index: 1.3910; n20/D 1.391; n20/D 1.391(lit.)
• Vapor Pressure: 2.9 mmHg ( 20 °C)
• Vapor Density: 5.11 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: RM6475000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 2524; UN2524
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10; 10-36/37/38; R:10-36/37
• Safety Statements: 16-36/39-45; 26-37-60; S:9-16-26
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2524 3/PG 3

Product Information

• Purity: ≥98.0% (GC); 97%; 98%
• Grade: anhydrous; purum; reagent grade
• Evaporation Residue: <0.0005%
• Impurities: <0.003% water; <0.005% water(100 mL pkg)
• Linear Formula: CH(OC2H5)3

DETAILS

MP Biomedicals - 05209901

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157013

(1,1′,1′′-[Methylidynetris(oxyl)]-tris[ethanel])
1 ml = approx. 0.90 g

Sigma Aldrich - T60453

Packaging
1 L in glass bottle
20 L in steel drum
500 mL in glass bottle

Sigma Aldrich - 304050

Packaging
1, 2 L in Sure/Seal™
100 mL in Sure/Seal™

REFERENCES

• For further reactions of alkyl orthoformates, see Trimethyl orthoformate, A13760.
• Acid-catalyzed reaction with an arylamine gives the N-ethoxymethylene derivative (imidic ester); see, e.g.: Org. Synth. Coll., 4, 464 (1963); reduction (NaBH₄) gives the monomethyl amine: Synthesis, 55 (1974).
• Due to their intrinsic dehydrating property, orthoformates are convenient reagents for acetalization of carbonyl compounds, under acid catalysis, e.g. tosic acid: J. Am. Chem. Soc., 60, 1905 (1938); J. Org. Chem., 20, 1695 (1955), or acidic ion-exchange resin: Synthesis, 348 (1974). Selective catalysis with NBS has been found to give high yields of acetals under almost neutral conditions: Synlett, 1456 (1999).
• In the presence of BF₃ etherate, is a source of the diethoxycarbenium ion: Synth. Commun., 19, 2307 (1989), a selective alkylating agent and a useful intermediate for the diethoxymethylenation of ketones, to give protected ?-ketoaldehydes: J. Org. Chem., 46, 2557 (1981). For a similar reaction with enamines to give the same products, see: Chem. Lett., 1307 (1982); Bull. Chem. Soc. Jpn., 57, 1876 (1984).
• Orthoformates have also found use in the electrophilic formylation of activated aromatic species, e.g.: phenols (in the presence of AlCl₃): Chem. Ber., 96, 308 (1963); pyrrole derivatives (with TFA): Austral. J. Chem., 25, 1979 (1972).