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75580

Triethyl orthoacetate

purum, ≥98.0% (GC)

Synonym(s):

1,1,1-Triethoxyethane

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100 mL

Available to ship TODAYfromMILWAUKEE

$51.10
500 mL

Available to ship TODAYfromMILWAUKEE

$140.00

About This Item

Linear Formula:
CH3C(OC2H5)3
CAS Number:
Molecular Weight:
162.23
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-112-4
Beilstein/REAXYS Number:
506201
MDL number:
Assay:
≥98.0% (GC)
Form:
liquid

$51.10


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grade

purum

Quality Level

assay

≥98.0% (GC)

form

liquid

refractive index

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

InChI key

NDQXKKFRNOPRDW-UHFFFAOYSA-N

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.


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1 of 1

This Item
T60402T60607T60453
assay

≥98.0% (GC)

assay

97%

assay

97%

assay

98%

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

refractive index

n20/D 1.396

refractive index

n20/D 1.396 (lit.)

refractive index

n20/D 1.402 (lit.)

refractive index

n20/D 1.391 (lit.)

density

0.885 g/mL at 25 °C (lit.)

density

0.885 g/mL at 25 °C (lit.)

density

0.876 g/mL at 25 °C (lit.)

density

0.891 g/mL at 25 °C (lit.)

form

liquid

form

-

form

-

form

liquid

bp

142 °C (lit.)

bp

142 °C (lit.)

bp

155-160 °C (lit.)

bp

146 °C (lit.)


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pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

flash_point_f

102.2 °F - Non-equilibrium method

flash_point_c

39 °C - Non-equilibrium method

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter



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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)
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)



Global Trade Item Number

SKUGTIN
B5386-5MG04061832895789
B5386-25MG04061833433799
B5386-100MG04061833433782
75580-100ML04061837015953
75580-500ML04061837015960

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