ChemicalBook CAS DataBase List 123-06-8

123-06-8

Name	Ethoxymethylenemalononitrile
CAS	123-06-8
EINECS(EC#)	204-597-0
Molecular Formula	C6H6N2O
MDL Number	MFCD00001854
Molecular Weight	122.12
MOL File	123-06-8.mol

Synonyms

2-(ETHOXYMETHYLENE)MALONONITRILE 2-(ETHOXYMETHYLIDENE)MALONONITRILE ETHOXYMETHYLENEMALONITRILE ETHOXYMETHYLENEMALONONITRILE ETHOXYMETHYLENMALONONITRILE LABOTEST-BB LT01148236 PROPANEDINITRILE, (ETHOXYMETHYLENE)- (beta-Ethoxymethylene)malononitrile (b-Ethoxymethylene)malononitrile (ethoxymethylene)-malononitril (ethoxymethylene)-propanedinitril (Ethoxymethylene)propanedinitrile 1,1-Dicyano-2-ethoxyethene 1-Ethoxy-2,2-dicyanoethene 2-Cyano-3-ethoxyacrylonitrile 2-Ethoxy-1,1-ethenedicarbonitrile a-Cyano-b-ethoxyacrylonitrile alpha-Cyano-beta-ethoxyacrylonitrile Ethoxymethylene-malonic acid dinitrile Malononitrile, (ethoxymethylene)-

Chemical Properties

Appearance	Off White to Pale Yellow
Melting point	64-66 °C(lit.)
Boiling point	160 °C12 mm Hg(lit.)
density	1.2236 (rough estimate)
refractive index	1.4738 (estimate)
Fp	155 °C
storage temp.	Inert atmosphere,Room Temperature
solubility	DMF, DMSO, Ethanol, Methanol
form	Liquid
color	Clear colorless to yellow
Water Solubility	insoluble
Detection Methods	GC,NMR
BRN	1634241
InChI	1S/C6H6N2O/c1-2-9-5-6(3-7)4-8/h5H,2H2,1H3
InChIKey	OEICGMPRFOJHKO-UHFFFAOYSA-N
SMILES	CCO\C=C(\C#N)C#N
Uses	Chemical intermediate. less more
CAS DataBase Reference	123-06-8(CAS DataBase Reference)
NIST Chemistry Reference	Propanedinitrile, (ethoxymethylene)-(123-06-8)
EPA Substance Registry System	123-06-8(EPA Substance)

Safety Data

Symbol(GHS)	GHS07,GHS08
Signal word	Danger
Hazard statements	H302-H317-H334
Precautionary statements	P280-P301+P312+P330-P302+P352
Hazard Codes	Xn,T,Xi
Risk Statements	R22:Harmful if swallowed. R42/43:May cause sensitization by inhalation and skin contact . R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . R43:May cause sensitization by skin contact. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S22:Do not breathe dust . S36/37:Wear suitable protective clothing and gloves . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . S24/25:Avoid contact with skin and eyes . less more
RIDADR	3439
WGK Germany	3
RTECS	OO3850000
F	21
TSCA	Yes
HazardClass	6.1
PackingGroup	III
HS Code	29269090
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Resp. Sens. 1 Skin Sens. 1
Toxicity	mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689, less more

Raw materials And Preparation Products

Hazard Information

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

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

122-51-0

109-77-3

123-06-8

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.

Material Safety Data Sheet(MSDS)

Spectrum Detail

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