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Ethoxymethylenemalononitrile

Ethoxymethylenemalononitrile Structure
CAS No.
123-06-8
Chemical Name:
Ethoxymethylenemalononitrile
Synonyms
2-(ETHOXYMETHYLENE)MALONONITRILE;2-(Ethoxymethylene)propanedinitrile;ononitriL;ETHOXYMETHYLENEMALONITRILE;(Ethoxymethylene)propanedinitrile;usafkf-10;NSC 27792;USAF KF-10;usafa-9230;USAF a-9230
CBNumber:
CB9767407
Molecular Formula:
C6H6N2O
Molecular Weight:
122.12
MOL File:
123-06-8.mol
MSDS File:
SDS
Modify Date:
2023/8/31 15:30:57

Ethoxymethylenemalononitrile 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

Risk and Safety Statements

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  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
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,
NFPA 704
1
3 1

Ethoxymethylenemalononitrile price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) E6200 (Ethoxymethylene)malononitrile 98% 123-06-8 25G ₹3507.3 2022-06-14 Buy
Sigma-Aldrich(India) E6200 (Ethoxymethylene)malononitrile 98% 123-06-8 100G ₹8497.63 2022-06-14 Buy
TCI Chemicals (India) E0649 (Ethoxymethylene)malononitrile min. 98.0 % 123-06-8 25G ₹3600 2022-05-26 Buy
Product number Packaging Price Buy
E6200 25G ₹3507.3 Buy
E6200 100G ₹8497.63 Buy
E0649 25G ₹3600 Buy

Ethoxymethylenemalononitrile Chemical Properties,Uses,Production

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.

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.
Ethoxymethylenemalononitrile

Synthesis Reference(s)

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

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.

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ETHOXYMETHYLENEMALONONITRILE ETHOXYMETHYLENMALONONITRILE (beta-Ethoxymethylene)malononitrile (b-Ethoxymethylene)malononitrile (ethoxymethylene)-malononitril (ethoxymethylene)-propanedinitril 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)- USAF a-9230 USAF KF-10 usafa-9230 LABOTEST-BB LT01148236 2-(ETHOXYMETHYLIDENE)MALONONITRILE PROPANEDINITRILE, (ETHOXYMETHYLENE)- usafkf-10 ETHOXY METHYLENE MALONOITRILE- Ethoxy methlenemalononitrile 1-Ethoxy-2,2-dicyanoethylene Ethoxymethylenemalononitrile ,98% Ethoxymethylenemalononiyrile NSC 27792 α-Cyano-β-ethoxyacrylonitrile Propanedinitrile, 2-(ethoxyMethylene)- Ethoxy heartland of Methyl Malononitrile (Ethoxymethylene)malononitrile> Ethoxy malononitrile Ethoxymethylenmalononitril ETHOXYMETHYLENEMALONITRILE (Ethoxymethylene)propanedinitrile 2-(ETHOXYMETHYLENE)MALONONITRILE 2-(Ethoxymethylene)propanedinitrile ononitriL 2-(Ethoxymethylene)propanedinitrile (or) 2-(ethoxymethylene)malononitrile ethoxymethylmalonitrile 2-(ethoxymethylene)malonitrile 123-06-8 C6H6N20 C2H5OCHCCN2 Organic Building Blocks Nitrogen Compounds Cyanides/Nitriles Building Blocks C6 to C7 Aliphatic Compound Miscellaneous API intermediates Various Intermediates Intermediates C6 to C7 Cyanides/Nitriles Nitrogen Compounds Pharmaceutical Intermediates