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75580

Sigma-Aldrich

Triethyl orthoacetate

purum, ≥98.0% (GC)

Synonym(s):

1,1,1-Triethoxyethane

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100 MG
CN¥2,176.58

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100 MG
CN¥2,176.58

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

CN¥2,176.58


Estimated to ship onMay 08, 2025Details


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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.)

functional group

ether

SMILES string

CCOC(C)(OCC)OCC

InChI

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

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This Item
SAB1411646SAB4500345HPA067064
Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

biological source

rabbit

biological source

rabbit

biological source

rabbit

biological source

rabbit

conjugate

unconjugated

conjugate

unconjugated

conjugate

unconjugated

conjugate

unconjugated

product line

Prestige Antibodies® Powered by Atlas Antibodies

product line

-

product line

-

product line

Prestige Antibodies® Powered by Atlas Antibodies

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Application

Triethyl orthoacetate is a general reagent used to functionalize alcohols with acetate groups.[1] It can be used in following reactions:
  • Stereocontrolled total synthesis of a naturally occuring indole alkaloid, (−)-aspidophytine.[2]
  • Conversion of allylic alcohols to γ,δ-unsaturated esters under mild acidic condition, a reaction popularly known as Johnson–Claisen rearrangement.[3]
  • Synthesis of heterocycles such as 2-oxazolines and quinazolin-4(3H)-one derivatives.[4][5][6]

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

Regulatory Information

危险化学品

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    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)
    Clay catalysis: condensation of orthoesters with O-substituted aminoaromatics into heterocycles.
    Villemin D, et al.
    Synthetic Communications, 26(15), 2895-2899 (1996)
    Reaction of orthoesters with alcohols in the presence of acidic catalysts: A study.
    Kumar, HM et al.
    Indian J. Chem. B, 44B(8), 1686-1692 (2005)
    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)
    Stereocontrolled total synthesis of (−)-aspidophytine.
    Sumi S, et al.
    Tetrahedron, 59(43), 8571-8587 (2003)

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