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

L06004 Triethyl orthoacetate, 98%

Numéro CAS
78-39-7
Synonymes
Ethyl orthoacetate
Orthoacetic acid triethyl ester

Dimensions Prix ($) Quantité Disponibilité
100ml 30,95
500ml 86,67
2500ml 283,25
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Triethyl orthoacetate, 98%

MDL
MFCD00009223
EINECS
201-112-4

Propriétés chimiques

Formule
CH3C(OCH2CH3)3
Poids formulaire
162.23
Point d'ébullition
142-143°
Point d'éclair
32°(89°F)
Densité
0.887
Indice de réfraction
1.3970
Sensibilité
Moisture Sensitive
Solubilité
Slightly miscible with water.

Applications

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.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Beilstein
506201
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2915.39
TSCA
Yes
RTECS
KJ4075000

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Analytique et matériel de laboratoire