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479047

Sigma-Aldrich

2,2-Dimethoxyacetaldehyde solution

60 wt. % in H2O

Synonym(s):

Glyoxal 1-(dimethyl acetal), Glyoxal dimethyl acetal

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About This Item

Linear Formula:
(CH3O)2CHCHO
CAS Number:
Molecular Weight:
104.10
Beilstein/REAXYS Number:
1850744
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

concentration

60 wt. % in H2O

refractive index

n20/D 1.414

bp

100 °C

density

1.15 g/mL at 25 °C

functional group

acetal
aldehyde
ether

storage temp.

2-8°C

SMILES string

[H]C(=O)C(OC)OC

InChI

1S/C4H8O3/c1-6-4(3-5)7-2/h3-4H,1-2H3

InChI key

OGFKTAMJLKHRAZ-UHFFFAOYSA-N

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General description

This product is a 60wt% solution of 2,2-dimethoxyacetaldehyde (glyoxal dimethyl acetal) in water. The aldol condensation of 2,2-dimethoxyacetaldehyde with acetoacetic ester in the absence of the catalyst and solvent has been reported. It participates in the synthesis of isoxazoline vinyl ester pseudopeptides and tetrahydro-β-carboline derivatives of barbituric acid analogs.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

169.0 °F

flash_point_c

76.1 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Catalyst-Free Aldol Additions of 1,3-Dicarbonyl Compounds.
Rohr K and Mahrwald R.
Advanced Synthesis & Catalysis, 350(18), 2877-2880 (2008)
Design and synthesis of Pictet-Spengler condensation products that exhibit oncogenic-RAS synthetic lethality and induce non-apoptotic cell death.
Skouta R, et al.
Bioorganic & Medicinal Chemistry Letters, 22(17), 5707-5713 (2012)
Synthesis and activity of isoxazoline vinyl ester pseudopeptides as proteasome inhibitors.
Marastoni M, et al.
Journal of Peptide Science, 20(4), 258-265 (2014)
Paolo Ziosi et al.
ChemSusChem, 11(13), 2202-2210 (2018-05-16)
A new process for the synthesis of hydroxytyrosol (3,4-dihydroxyphenylethanol), the most powerful natural antioxidant currently known, by means of a two-step approach is reported. Catechol is first reacted with 2,2-dimethoxyacetaldehyde in basic aqueous medium to produce the corresponding mandelic derivative

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