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Triethyl orthoformate

Catalog No. A13587 Name Alfa Aesar
CAS Number 122-51-0 Website
M. F. C7H16O3 Telephone
M. W. 148.20014 Fax
Purity 98% Email
Storage Chembase ID: 104743

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 Pictograms GHS02
GHS Pictograms GHS07
GHS Hazard statements H226-H315-H319-H335
European Hazard Symbols Irritant 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
Hazard Class 3
UN Number UN2524
Packing Group III

DETAILS

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).