Ethoxymethylenemalononitrile Chemical Properties

Melting point:

64-66 °C(lit.)

Boiling point:

160 °C12 mm Hg(lit.)

Density 

1.2236 (rough estimate)

refractive index 

1.4738 (estimate)

Flash point:

155 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMF, DMSO, Ethanol, Methanol

form 

Liquid

color 

Clear colorless to yellow

Water Solubility 

insoluble

BRN 

1634241

InChIKey

OEICGMPRFOJHKO-UHFFFAOYSA-N

CAS DataBase Reference

123-06-8(CAS DataBase Reference)

NIST Chemistry Reference

Propanedinitrile, (ethoxymethylene)-(123-06-8)

EPA Substance Registry System

Propanedinitrile, (ethoxymethylene)- (123-06-8)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

22-42/43-23/24/25-43-20/21/22-R42/43-R23/24/25-R22

Safety Statements 

22-36/37-45-36/37/39-26-36-24/25-S45-S36/37/39-S26-S22

RIDADR 

3439

WGK Germany 

3

RTECS 

OO3850000

F 

21

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Toxicity

mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689,

MSDS

• Language:English Provider:Ethoxymethylenemalononitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethoxymethylenemalononitrile Usage And Synthesis

Description

Ethoxymethylenemalononitrile (EMMN) is an orange solid and the melting point of EMMN is 64–66 °C[1].It is an inexpensive reagent. As a functionalized malono-nitrile, it is widely used to synthesize pyrazoles, pyrimidines and a variety of fused heterocyclic systems.

Chemical Properties

Off White to Pale Yellow

Uses

Chemical intermediate.

Uses

Ethoxymethylene Malononitrile (cas# 123-06-8) is a compound useful in organic synthesis.

Preparation

Triethyl orthoformate (67.3 mg, 0.454 mol) and malononitrile (20.0 mg,0.302 mol)  were andded to acetic anhydride (77.2 gm, 0.75 moles) and the mixture was refluxed for 4-5 h at 110-140°C. The reaction was monitored by GC. After the reaction is complete, it is cooled to room temperature. Concentrated the mixture at 70°C at reduced pressure to yield crude solid product and the pure product (Ethoxymethylenemalononitrile) was obtained through purified either by vacuum distillation.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 3279, 1969 DOI: 10.1017/S0009838800024678

Synthesis

General procedure for the synthesis of 2-(ethoxymethylene)malononitrile from triethyl orthoformate and malononitrile: Triethyl orthoformate (67.3 g, 0.454 mol) was mixed with malononitrile (20.0 g, 0.302 mol) in acetic anhydride (77.2 g, 0.75 mol), and the reaction was carried out under reflux for 4-5 hours at 110-140 °C. The reaction process was monitored by gas chromatography (GC). Upon completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, the reaction mixture was concentrated under reduced pressure at 70 °C to afford the crude product 2-(ethoxymethylene)malononitrile. The crude product was further purified by vacuum distillation to give the pure 2-(ethoxymethylene)malononitrile.

References

[1] Faria J, et al. Ethoxymethylenemalononitrile. Synlett , 2013; 24: 0264–0265.
[2] Maurício , et al. Synthesis and antileishmanial evaluation of 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole derivatives. Bioorganic & Medicinal Chemistry Letters, 2011; 21: 7451-7454.

Ethoxymethylenemalononitrile(123-06-8)Related Product Information

• Diethyl methylmalonate
• Ethoxyquin
• 2-Methylpropanedioic acid
• CITRATE SYNTHASE
• 2,2-DIMETHYL-1,3-PROPANEDIAMINE
• Tosylmethyl isocyanide
• Malononitrile
• Ethyl 3-ethoxypropionate
• Diethyl ethoxymethylenemalonate
• ETHOXYLATED COCOAMINE (LATEX STABILIZER)
• Ethylamine hydrochloride
• 2-Methoxyethyl acetoacetate
• Poly(oxy-1,2-ethanediyl), .alpha.-hydro-.omega.-(1-oxo-2-propenyl)oxy-, ether with 2,2-bis(hydroxymethyl)-1,3-propanediol (4:1)
• Ethoxyamine hydrochloride
• CHLOROMETHYLDIMETHYLETHOXYSILANE
• 1,1,2-TRIETHOXYETHANE
• Ethoxyacetic acid
• Acetoxyacetyl chloride