GLYOXAL DIMETHYL ACETAL Chemical Properties

Boiling point:

100 °C

Density 

1.15 g/mL at 25 °C

refractive index 

n20/D 1.414

Flash point:

169 °F

storage temp. 

2-8°C

form 

liquid

color 

Clear colourless

Water Solubility 

Fully miscible in water.

BRN 

1850744

InChI

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

InChIKey

OGFKTAMJLKHRAZ-UHFFFAOYSA-N

SMILES

C(=O)C(OC)OC

EPA Substance Registry System

Acetaldehyde, dimethoxy- (51673-84-8)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

43-38-11

Safety Statements 

24-37-36/37-16

RIDADR 

UN 2398 3/PG 2

WGK Germany 

-

TSCA 

Yes

HazardClass 

CBL

HS Code 

2912490090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

GLYOXAL DIMETHYL ACETAL Usage And Synthesis

Uses

Glyoxal dimethyl acetal is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuffs.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1343, 1988 DOI: 10.1080/00397918808078802

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.

Synthesis

NaIO4 (3 g, 14 mmol) was added to a suspension of DCM (30 mL) containing silica (10 g), followed by the addition of olefin 9 (355 mg, 2 mmol) pre-dissolved in DCM (20 mL). The reaction mixture was stirred at room temperature for 30 min and then filtered. The solid residue was washed twice with DCM (20 mL). The combined organic phases were dried with MgSO4, filtered and concentrated under reduced pressure under strictly controlled conditions (20 °C, 300 mmHg) to avoid loss of aldehyde 10 due to high volatility. A clear liquid-like crude product (350 mg, 85% yield) was finally obtained, which was directly used in the subsequent reaction without further purification.1H NMR (400 MHz, CDCl3): δ= 9.47 (d, J = 1.5 Hz, 1H, 1-H), 4.50 (d, J = 1.5 Hz, 1H, 2-H), 3.46 (s, 6H, 3-H) ppm. 13C NMR (100 MHz, CDCl3): δ= 199.2 (1-C), 122.3 (2-C), 54.6 (3-C) ppm.

References

[1] Tetrahedron Asymmetry, 2013, vol. 24, # 18, p. 1175 - 1181
[2] Patent: CN105753834, 2016, A. Location in patent: Paragraph 0040; 0041; 0042
[3] Patent: CN105153110, 2017, B. Location in patent: Paragraph 0034-0036

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