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232599

Sigma-Aldrich

Ethyl methoxyacetate

97%

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About This Item

Linear Formula:
CH3OCH2COOC2H5
CAS Number:
Molecular Weight:
118.13
Beilstein:
1744761
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

refractive index

n20/D 1.401 (lit.)

bp

44-45.5 °C/9 mmHg (lit.)

density

1.007 g/mL at 25 °C (lit.)

functional group

ester
ether

SMILES string

CCOC(=O)COC

InChI

1S/C5H10O3/c1-3-8-5(6)4-7-2/h3-4H2,1-2H3

InChI key

JLEKJZUYWFJPMB-UHFFFAOYSA-N

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Application

Ethyl methoxyacetate was used:
  • as acyl donor during the preparation of enantiomers of several phenylethylamines
  • as acylation reagent for the aminolysis of 1-phenylethanamine
  • in an industrial, lipase-catalysed kinetic resolution of primary amine

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

114.8 °F - closed cup

Flash Point(C)

46 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Lourdes Muñoz et al.
Organic & biomolecular chemistry, 9(23), 8171-8177 (2011-10-06)
Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine
Ulf Hanefeld
Organic & biomolecular chemistry, 1(14), 2405-2415 (2003-09-06)
Commonly, hydrolase-catalysed reactions are used for kinetic resolutions of alcohols, amines and acids. Only a few applications in total syntheses have been described. Most of these examples are for the synthesis of amides and peptides. Here, the synthesis of all
T S Shih et al.
Archives of environmental health, 56(1), 20-25 (2001-03-21)
Urinary 2-methoxy acetic acid reportedly has a long half-life (77.1 hr) in humans. The authors studied urinary 2-methoxy acetic acid in a group of 18 workers exposed to 2-methoxy ethanol from Monday to Saturday following a 7-d cease in production.
Saija Sirén et al.
Molecules (Basel, Switzerland), 25(4) (2020-02-23)
The enantiomers of aromatic 4-dibenzocyclooctynol (DIBO), used for radiolabeling and subsequent conjugation of biomolecules to form radioligands for positron emission tomography (PET), were separated by kinetic resolution using lipase A from Candida antarctica (CAL-A). In optimized conditions, (R)-DIBO [(R)-1, ee
C Saito et al.
Biotechnic & histochemistry : official publication of the Biological Stain Commission, 74(1), 40-48 (1999-04-06)
An in situ hybridization procedure resulting in both high resolution and sensitivity was established by using the removable methyl methacrylate resin, Technovit 9100. Young bicellular pollen of tobacco (Nicotiana tabacum L. SR-1) was embedded in Technovit 9100 resin and sectioned.

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