Triethyl orthoformate

• Catalog No.: A13587
• CAS Number: 122-51-0
• M. F.: C7H16O3
• M. W.: 148.20014
• Purity: 98%

SYNONYMS

• Title: 原甲酸三乙酯
• IUPAC name: (diethoxymethoxy)ethane
• IUPAC Traditional name: triethyl orthoformate
• Synonyms: Ethyl orthoformate; Orthoformic acid triethyl ester

DATABASE IDS

• MDL Number: MFCD00009230
• Beilstein Number: 605384
• CAS Number: 122-51-0
• EC Number: 204-550-4
• Merck Index: 146884

PROPERTIES

• Purity: 98%
• Boiling Point: 144-146°C
• Density: 0.891
• Flash Point: 30°C(86°F)
• Melting Point: -61°C
• Refractive Index: 1.3910
• GHS Hazard statements: H226-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-36/37/38
• RTECS: RM6475000
• Safety Statements: 26-37-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2524
• Packing Group: III

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).