Diethoxyacetonitrile Chemical Properties

Melting point:

-19--18 °C (lit.)

Boiling point:

167.7 °C/773 mmHg (lit.)

Density 

0.929 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4(lit.)

Flash point:

121 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

liquid

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H11NO2/c1-3-8-6(5-7)9-4-2/h6H,3-4H2,1-2H3

InChIKey

UDELMRIGXNCYLU-UHFFFAOYSA-N

SMILES

C(#N)C(OCC)OCC

EPA Substance Registry System

Acetonitrile, diethoxy- (6136-93-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-20/21/22-36/37/38

Safety Statements 

16-26-27-36/37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3.2

PackingGroup 

III

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

Diethoxyacetonitrile Usage And Synthesis

Uses

Diethoxyacetonitrile may be used in the preparation of methyl 5-diethoxymethylimidazole-4-carboxylate, via anionic cycloaddition reaction with methyl isocyanoacetate.

General Description

Diethoxyacetonitrile is a 2,2-dialkoxyalkanenitrile derivative. Reaction of hydrocyanic acid with various ortho esters of aliphatic and aromatic acids in the presence of acidic catalyst has been reported to afford diethoxyacetonitrile. Houben-Hoesch reaction of diethoxyacetonitrile with 1,2,4-trimethoxybenzene affords tris(2,4,5-trimethoxyphenyl)methane.

Synthesis

The general procedure for the synthesis of diethoxyacetonitrile from 2,2-diethoxyacetamide is as follows (cf. Inami, K., Shiba, T., Bull. Chem. Soc. Jpn., 1985, 58, 352): 2,2-diethoxyacetamide (7.13 g, 49.04 mmol) was dissolved in toluene (50 mL), followed by the addition of triethylamine (NEt3, 10.4 mL) and phosphorus pentoxide (P2O5, 9.04 g, 64.32 mmol). The reaction mixture was stirred for 1 hour. Upon completion of the reaction, the solvent was first removed by distillation at atmospheric pressure and then changed to reduced pressure distillation to collect the diethoxyacetonitrile to give a clear, colorless liquid product (4.049 g, 64% yield). The boiling point of the product was 100 °C (12-15 mmHg). IR spectra (KBr, cm^-1): 2983, 2937, 2896 (υC-H), 2247 (υC≡N), 1067 (δC-O). NMR hydrogen spectrum (CDCl3): δ 1.27 (6H, t, J = 8.0 Hz, 2 × CH3), 3.73 (4H, m, 2 × CH2), 5.31 (1H, s, CH). Low Resolution Mass Spectrometry (LREIMS): measured value 130.13 (M+H), calculated value C6H11NO2 129.08.

References

[1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 1, p. 352 - 360
[2] Patent: WO2008/38018, 2008, A1. Location in patent: Page/Page column 63-64
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 2660
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 2660
[5] Chemische Berichte, 1934, vol. 67, p. 1507,1511

Diethoxyacetonitrile(6136-93-2)Related Product Information

• Acetonitrile
• DIFLUOROACETONITRILE
• Iminodiacetonitrile
• 1,4-Phenylenediacetonitrile
• Bis(acetonitrile)dichloropalladium(II)
• 3,3-Diethoxypropionitrile
• 3,3-DIETHOXY-1-PROPANOL
• 3,3-DIETHOXY-PROPIONIC ACID
• 20(22),5BETA-CARDENOLID-19-AL-3BETA,5BETA,14BETA-TRIOL 3-(O->1BETA)-D-CYANOPYRANOSIDE
• Methoxyacetonitrile
• 2,2-DIETHOXYPROPIONITRILE
• Diethoxyacetonitrile