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

A13587 Triethyl orthoformate, 98%

CAS Number
122-51-0
Synonyms
Ethyl orthoformate
Orthoformic acid triethyl ester

Size Price ($) Quantity Availability
500ml 34.71
2500ml 109.18
10000ml 362.56
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Triethyl orthoformate, 98%

MDL
MFCD00009230
EINECS
204-550-4

Chemical Properties

Formula
C7H16O3
Formula Weight
148.20
Melting point
-61°
Boiling Point
144-146°
Flash Point
30°(86°F)
Density
0.891
Refractive Index
1.3910
Sensitivity
Moisture Sensitive
Solubility
Miscible with alcohols, acetone, ethers and chloroform. Slightly miscible with water.

Applications

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.

Notes

Moisture sensitive. Incompatible with acids and strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

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

Precautionary Statements: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6884
Beilstein
605384
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2915.13
TSCA
Yes
RTECS
RM6475000

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