237876
Trimethyl orthoacetate
99%
Synonym(s):
1,1,1-Trimethoxyethane
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About This Item
Linear Formula:
CH3C(OCH3)3
CAS Number:
Molecular Weight:
120.15
Beilstein/REAXYS Number:
1098338
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
99%
form
liquid
refractive index
n20/D 1.388 (lit.)
bp
107-109 °C (lit.)
density
0.944 g/mL at 25 °C (lit.)
functional group
ether
SMILES string
COC(C)(OC)OC
InChI
1S/C5H12O3/c1-5(6-2,7-3)8-4/h1-4H3
InChI key
HDPNBNXLBDFELL-UHFFFAOYSA-N
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General description
Kinetics and mechanism of gas-phase elimination of trimethyl orthoacetate has been examined over the temperature range of 310-369°C and pressure range of 50-130Torr.
Trimethyl orthoacetate is used to synthesize acrylonitrile intermediates via reaction with alcohols followed by Knoevenagel condensation.
Trimethyl orthoacetate is used to synthesize acrylonitrile intermediates via reaction with alcohols followed by Knoevenagel condensation.
Application
Trimethyl orthoacetate has been used in the preparation of 2-amino-9-(3-acyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines and 2-amino-9-(3-alkoxycarbonyl-oxymethyl-4-alkoxycarbonyloxybut -1-yl)purines.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Sens. 1B
Storage Class
3 - Flammable liquids
wgk_germany
WGK 1
flash_point_f
55.4 °F - closed cup
flash_point_c
13 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Transesterification of trimethyl orthoacetate: an efficient protocol for the synthesis of 4-alkoxy-2-aminothiophene-3-carbonitriles
Rao KV, et al.
Tetrahedron Letters, 54, 1274-1278 (2013)
D K Kim et al.
Bioorganic & medicinal chemistry, 7(8), 1715-1725 (1999-09-11)
A series of 2-amino-9-(3-acyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purin es (1-8) and 2-amino-9-(3-alkoxycarbonyl-oxymethyl-4-alkoxycarbonyloxybut -1-yl)purines (9-12) were synthesized as potential prodrugs of penciclovir. Treatment of 6-deoxypenciclovir with trimethyl orthoacetate or triethyl orthopropionate (1.2 equiv) in DMF in the presence of p-TsOH.H2O (0.1 equiv) followed by quenching
Edgar Márquez et al.
The journal of physical chemistry. A, 112(47), 12140-12142 (2008-11-01)
The gas-phase elimination kinetics of the title compounds have been examined over the temperature range of 310-369 degrees C and pressure range of 50-130 Torr. The reactions, in seasoned vessels, are homogeneous, unimolecular, and follow a first-order rate law. The
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