Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

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

L06004 Triethyl orthoacetate, 98%

CAS Number
78-39-7
Synonyms
Ethyl orthoacetate
Orthoacetic acid triethyl ester

Size Price ($) Quantity Availability
100ml 30.95
500ml 86.67
2500ml 283.25
Add to Cart Add to Quote Request View Item

Triethyl orthoacetate, 98%

MDL
MFCD00009223
EINECS
201-112-4

Chemical Properties

Formula
CH3C(OCH2CH3)3
Formula Weight
162.23
Boiling Point
142-143°
Flash Point
32°(89°F)
Density
0.887
Refractive Index
1.3970
Sensitivity
Moisture Sensitive
Solubility
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.

Literature References

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.

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

Beilstein
506201
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2915.39
TSCA
Yes
RTECS
KJ4075000

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware