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78-39-7 - Triethyl orthoacetate, 98% - Ethyl orthoacetate - Orthoacetic acid triethyl ester - L06004 - Alfa Aesar

L06004 Triethyl orthoacetate, 98%

Codice CAS
78-39-7
Sinonimi
Ethyl orthoacetate
Orthoacetic acid triethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
100ml 33,10
500ml 99,70
2500ml 285,00
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Triethyl orthoacetate, 98%

MDL
MFCD00009223
EINECS
201-112-4

Proprietà chimiche

Formula
CH3C(OCH2CH3)3
Peso formula
162.23
Punto di ebollizione
142-143°
Punto di infiammabilità
32°(89°F)
Densità
0.887
Indice di rifrazione
1.3970
Sensibilità
Moisture Sensitive
Solubilità
Slightly miscible with water.

Applicazioni

Triethyl orthoacetate is used as pharmaceutical and water scavenger. It is also used in organic synthesis to introduce the acetate group into an alcohol. It is involved in the Johnson-Claisen rearrangement.

Note

Moisture sensitive. Incompatible with strong oxidizing agents.

Letteratura

Reagent for facile esterification of sulfonic and carboxylic acids: Tetrahedron Lett., 34, 7355 (1993).

The products with allylic alcohols undergo Claisen allyl ether rearrangement, with addition of a 2-carbon unit and repositioning of the double bond: J. Am. Chem. Soc., 92, 741 (1970); Tetrahedron Lett., 21, 1285 (1980):

For further examples, see: Org. Synth. Coll., 6, 584 (1988); 7, 164 (1990).

Reaction with BF3 etherate gives the moderately stable selective alkylating agent, methyl diethoxycarbenium tetrafluoroborate: Synth. Commun., 19, 2307 (1989). Compare Triethyl­ orthoformate, A13587.

Under mild acid catalysis, reacts with ethynyl alcohols to give allenic esters, which can be conjugated over alumina. For examples, see: Org. Synth. Coll., 8, 251 (1993):

Yang, J.; Su, G.; Ren, Y.; Chen, Y. Design, synthesis and evaluation of isoxazolo [5, 4-d] pyrimidin-4 (5H)-one derivatives as antithrombotic agents. Bioorg. Med. Chem. Lett. 2015, 25 (3), 492-495.

Shawali, A. S.; Sami, A. Annulated 3-Amino-4-Imino-Pyrimidines: Their Utility as Useful Precursors for the Synthesis of Fused Heterocycles. Curr. Org. Synth. 2015, 12 (4), 391-430.

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-P280a-P280a-P240-P303+P361+P353-P305+P351+P338-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
506201
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2915.39
TSCA
Yes
RTECS
KJ4075000

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