Ethyl 2,2-diethoxyethylcyanoacetate Chemical Properties

Boiling point:

86°C 0,1mm

Density 

1,025 g/cm³

Flash point:

>110°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Methanol

form 

Oil

color 

Clear Colorless to Pale Yellow

CAS DataBase Reference

52133-67-2(CAS DataBase Reference)

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

UN3276

HazardClass 

6.1

HS Code 

2926907090

Ethyl 2,2-diethoxyethylcyanoacetate Usage And Synthesis

Chemical Properties

Colourless Liquid

Uses

Ethyl 2-Cyano-4,4-diethoxybutyrate (cas# 52133-67-2) is a compound useful in organic synthesis.

Synthesis

Method AI: Synthesis of ethyl 2-cyano-4,4-diethoxybutyrate (xlii-a): In a dry reaction flask, ethyl 2-cyanoacetate (11.4 g, 101 mmol, 5.0 eq.), potassium carbonate (2.8 g, 20 mmol, 1.0 eq.), and sodium iodide (200 mg, 1.3 mmol, 0.06 eq.) were added in sequence. Subsequently, 2-bromo-1,1-diethoxyethane (4 g, 20 mmol, 1.0 eq.) was slowly added to the mixture. The reaction mixture was refluxed at 145°C for 4 hours with reference to J. Chem. Soc., 1960,131-138. After completion of the reaction, it was cooled to room temperature and the product was purified by silica gel column chromatography with petroleum ether/ethyl acetate as eluent (gradient elution: 80:1→40:1→40:1) to give 3.57 g of the target compound xii-a as a colorless oil in 78% yield.1H NMR (400 MHz, CDCl3): δ 4.70 (t, J=5.6 Hz, 1H), δ 4.26 (q, J=7.2Hz, 2H), 3.78-3.64 (m, 3H), 3.62-3.45 (m, 2H), 2.35-2.14 (m, 2H), 1.34 (q, J=7.2Hz, 3H), 1.25-1.16 (m, 6H).

References

[1] Patent: US2015/307477, 2015, A1. Location in patent: Paragraph 1563
[2] Patent: JP6121658, 2017, B2. Location in patent: Paragraph 1270; 1271
[3] Archiv der Pharmazie, 2018, vol. 351, # 8,
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 12, p. 4064 - 4067
[5] Organic Letters, 2017, vol. 19, # 9, p. 2214 - 2217

Ethyl 2,2-diethoxyethylcyanoacetate(52133-67-2)Related Product Information

• Methylene dithiocyanate
• 3-CYANOPROPIONALDEHYDE DIMETHYL ACETAL
• Ethyl 2,2-diethoxyethylcyanoacetate
• 3-CYANOPROPIONALDEHYDE DIETHYL ACETAL
• ETHYL 2-CYANO-4,4-DIMETHOXYBUTANOATE