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75580

Sigma-Aldrich

Triethyl orthoacetate

purum, ≥98.0% (GC)

Synonym(s):

1,1,1-Triethoxyethane

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About This Item

Linear Formula:
CH3C(OC2H5)3
CAS Number:
Molecular Weight:
162.23
Beilstein:
506201
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

Assay

≥98.0% (GC)

form

liquid

refractive index

n20/D 1.396 (lit.)
n20/D 1.396

bp

142 °C (lit.)

density

0.885 g/mL at 25 °C (lit.)

SMILES string

CCOC(C)(OCC)OCC

InChI

1S/C8H18O3/c1-5-9-8(4,10-6-2)11-7-3/h5-7H2,1-4H3

InChI key

NDQXKKFRNOPRDW-UHFFFAOYSA-N

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Application

Triethyl orthoacetate is a general reagent used to functionalize alcohols with acetate groups. It can be used in following reactions:
  • Stereocontrolled total synthesis of a naturally occuring indole alkaloid, (−)-aspidophytine.
  • Conversion of allylic alcohols to γ,δ-unsaturated esters under mild acidic condition, a reaction popularly known as Johnson–Claisen rearrangement.
  • Synthesis of heterocycles such as 2-oxazolines and quinazolin-4(3H)-one derivatives.

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

102.2 °F - Non-equilibrium method

Flash Point(C)

39 °C - Non-equilibrium method

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Clay catalysis: condensation of orthoesters with O-substituted aminoaromatics into heterocycles.
Villemin D, et al.
Synthetic Communications, 26(15), 2895-2899 (1996)
An efficient and versatile method for the synthesis of optically active 2-oxazolines: an acid-catalyzed condensation of ortho esters with amino alcohols.
Kamata K, et al.
The Journal of Organic Chemistry, 63(9), 113-3116 (1998)
Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene.
Johnson WS, et al.
Journal of the American Chemical Society, 92(3), 741-743 (1970)
A new approach to the facile synthesis of mono-and disubstituted quinazolin-4 (3H)-ones under solvent-free conditions.
Salehi P, et al.
Tetrahedron Letters, 46(41), 7051-7053 (2005)
Stereocontrolled total synthesis of (−)-aspidophytine.
Sumi S, et al.
Tetrahedron, 59(43), 8571-8587 (2003)

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