PROPARGYLALDEHYDE DIETHYL ACETAL Chemical Properties

Boiling point:

138-139.5 °C(lit.)

Density 

0.894 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.412(lit.)

Flash point:

90 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

Specific Gravity

0.894

color 

Clear light yellow

Water Solubility 

Slightly soluble in water.

BRN 

1701566

Stability:

Light Sensitive, Volatile

InChI

InChI=1S/C7H12O2/c1-4-7(8-5-2)9-6-3/h1,7H,5-6H2,2-3H3

InChIKey

RGUXEWWHSQGVRZ-UHFFFAOYSA-N

SMILES

C#CC(OCC)OCC

CAS DataBase Reference

10160-87-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

21

HazardClass 

3

PackingGroup 

III

HS Code 

29110000

MSDS

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

PROPARGYLALDEHYDE DIETHYL ACETAL Usage And Synthesis

Uses

Propargylaldehyde diethyl acetal is a useful reactant for the synthesis of alkenylsilanes via radical stereoselective hydrosilylation of alkynes with the help of Eosin Y and thiols as catalysts.

Chemical Properties

Clear light yellow liquid

Uses

Propargylaldehyde diethyl acetal is a useful reactant for the synthesis of alkenylsilanes via radical stereoselective hydrosilylation of alkynes with the help of Eosin Y and thiols as catalysts.

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 4723, 1976 DOI: 10.1016/S0040-4039(00)93007-7

Synthesis

General procedure for the synthesis of 3,3-diethoxyprop-1-yne from 2,3-dibromopropanal and ethanol: (2) Addition of sodium hydroxide to the anhydrous ethanol solution obtained in step (1). This was done by dissolving 155 kg of sodium hydroxide in 470 kg of anhydrous ethanol to prepare an anhydrous ethanol solution of sodium hydroxide, and refluxing the reaction mixture at 82 °C for 10 min. Upon completion of the reaction, separation and purification operations were carried out to obtain propargyl acetal diethyl acetal. First, the isolation and purification was carried out at 20 °C to remove solid impurities by centrifugation, followed by soaking in 80 kg of ethanol in a filter for 10 min, after which it was dried. The filtrate was transferred to a distillation flask and first distilled at atmospheric pressure until the temperature reached 100°C and the fractions were collected. Subsequently, decompression distillation was started, gradually increasing the vacuum to -0.09 MPa and maintaining the bottom temperature at 100 °C until the heating was stopped. Next, atmospheric distillation was carried out by setting the reflux ratio to 4:1, using a 600 mm packed column and controlling the bottom temperature at 120 °C. After distillation, the organic phases were combined and stirred with 10 kg of sodium hydroxide for 1 h, followed by filtration. The filtrate was added to the distillation unit and distilled under a vacuum of -0.097 MPa using a 600 mm distillation column with a set reflux ratio of 4:1. When the bottom temperature reached 50°C and the fraction temperature reached 42°C, the qualified product was collected. Finally, 60kg of qualified products with content >98% and moisture <0.1% were obtained.

References

[1] Patent: CN106749127, 2017, A. Location in patent: Paragraph 0057; 0061-0064; 0081; 0089-0094; 0115; 0119-0122

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