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Sigma-Aldrich

Trimethyl orthoacetate

99%

Synonym(s):

1,1,1-Trimethoxyethane

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About This Item

Linear Formula:
CH3C(OCH3)3
CAS Number:
1445-45-0
Molecular Weight:
120.15
Beilstein:
1098338
EC Number:
215-892-9
MDL number:
MFCD00008477
UNSPSC Code:
12352100
PubChem Substance ID:
24854275
NACRES:
NA.22

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.)

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.

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H317,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Sens. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

55.4 °F - closed cup

Flash Point(C)

13 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Takahide Murakami et al.
Acta biomaterialia, 84, 257-267 (2018-12-12)
Postoperative adhesion is a relevant clinical problem that causes a variety of clinical complications after abdominal surgery. The objective of this study is to develop a liquid-type antiadhesion agent and evaluate its efficacy in preventing tissue adhesion in a rat
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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