75580
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
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
InChI key
NDQXKKFRNOPRDW-UHFFFAOYSA-N
InChI
1S/C8H18O3/c1-5-9-8(4,10-6-2)11-7-3/h5-7H2,1-4H3
SMILES string
CCOC(C)(OCC)OCC
grade
purum
assay
≥98.0% (GC)
form
liquid
Quality Level
bp
142 °C (lit.)
density
0.885 g/mL at 25 °C (lit.)
functional group
ether
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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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 1
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
Regulatory Information
危险化学品
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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)
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)
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)
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