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122-51-0 - Triethyl orthoformate, 98% - Ethyl orthoformate - Orthoformic acid triethyl ester - A13587 - Alfa Aesar

A13587 Triethyl orthoformate, 98%

Codice CAS
122-51-0
Sinonimi
Ethyl orthoformate
Orthoformic acid triethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
500ml 34,50
2500ml 110,00
10000ml 366,00
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Triethyl orthoformate, 98%

MDL
MFCD00009230
EINECS
204-550-4

Proprietà chimiche

Formula
C7H16O3
Peso formula
148.20
Punto di fusione
-61°
Punto di ebollizione
144-146°
Punto di infiammabilità
30°(86°F)
Densità
0.891
Indice di rifrazione
1.3910
Sensibilità
Moisture Sensitive
Solubilità
Miscible with alcohols, acetone, ethers and chloroform. Slightly miscible with water.

Applicazioni

Triethyl orthoformate is used in Bodroux-Chichibabin aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with Grignard reagent. It is also used in the electrophilic formylation of activated aromatic species such as phenol.

Note

Moisture sensitive. Incompatible with acids and strong oxidizing agents.

Letteratura

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 ß-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).

For further reactions of alkyl orthoformates, see Trimethyl­ orthoformate, A13760.

Yar, M.; Shahzad, S.; Siddiqi, S. A.; Mahmood, N.; Rauf, A.; Anwar, M. S.; Chaudhry, A. A.; Rehman, I. Triethyl orthoformate mediated a novel crosslinking method for the preparation of hydrogels for tissue engineering applications: characterization and in vitro cytocompatibility analysis. Mater. Sci. Eng., C 2015, 56, 154-164.

Szczepankiewicz, W.; Kuźnik, N. Synthesis of 3-arylquinazolin-4(3H)-imines from 2-amino-N'-arylbenzamidines and triethyl orthoformate. Tetrahedron Lett. 2015, 56 (10), 1198-1199.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,6884
Beilstein
605384
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2915.13
TSCA
Yes
RTECS
RM6475000

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