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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:
51673-84-8
Molecular Weight:
104.10
Beilstein:
1850744
EC Number:
421-890-0
MDL number:
MFCD00134410
UNSPSC Code:
12352100
PubChem Substance ID:
24871595
NACRES:
NA.22

Quality Level

100

concentration

60 wt. % in H2O

refractive index

n20/D 1.414

bp

100 °C

density

1.15 g/mL at 25 °C

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
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

169.0 °F

Flash Point(C)

76.1 °C

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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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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