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237876

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

Quality Level

200

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

237876-5ML:
237876-500ML:
237876-VAR:
237876-BULK:
237876-100ML:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ4429
WXBD1263V
WXBC8654V
WXBC0171V
WXBB6768V

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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
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
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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