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Ethoxymethylenemalononitrile

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
MDL Number:
MFCD00001854
MOL File:
123-06-8.mol
MSDS File:
SDS
Last updated:2026-01-13 11:27:00
Product description Number Pack Size Price
(Ethoxymethylene)malononitrile 98% E6200 25g $41.6
(Ethoxymethylene)malononitrile 98% E6200 100g $90.1
(Ethoxymethylene)malononitrile >98.0%(GC) E0649 25g $84
EthoxymethyleneMalononitrile E892450 100g $120
EthoxymethyleneMalononitrile E892450 250g $270
More product size

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
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
CAS DataBase Reference 123-06-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 91PS2PWB1Q
NIST Chemistry Reference Propanedinitrile, (ethoxymethylene)-(123-06-8)
EPA Substance Registry System Propanedinitrile, (ethoxymethylene)- (123-06-8)
UNSPSC Code 12352100
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H317-H334
Precautionary statements  P280-P301+P312+P330-P302+P352
PPE dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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  TSCA listed
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,
NFPA 704
1
3 1

Ethoxymethylenemalononitrile price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich E6200 (Ethoxymethylene)malononitrile 98% 123-06-8 25g $41.6 2026-03-19 Buy
Sigma-Aldrich E6200 (Ethoxymethylene)malononitrile 98% 123-06-8 100g $90.1 2026-03-19 Buy
TCI Chemical E0649 (Ethoxymethylene)malononitrile >98.0%(GC) 123-06-8 25g $84 2026-03-19 Buy
TRC E892450 EthoxymethyleneMalononitrile 123-06-8 100g $120 2021-12-16 Buy
TRC E892450 EthoxymethyleneMalononitrile 123-06-8 250g $270 2021-12-16 Buy
Product number Packaging Price Buy
E6200 25g $41.6 Buy
E6200 100g $90.1 Buy
E0649 25g $84 Buy
E892450 100g $120 Buy
E892450 250g $270 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.

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.
Ethoxymethylenemalononitrile

Synthesis Reference(s)

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

Synthesis

Triethyl orthoformate

122-51-0

Malononitrile

109-77-3

Ethoxymethylenemalononitrile

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.

108-24-7
109-77-3
123-06-8
Synthesis of Ethoxymethylenemalononitrile from Acetic anhydride and Malononitrile
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View Lastest Price from Ethoxymethylenemalononitrile manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ethoxymethylenemalononitrile pictures 2023-04-26 Ethoxymethylenemalononitrile
123-06-8
US $0.00 / Kg 1Kg 99.0% up 50 tons per month Xinxiang Hongqi District Houyuan Trading Co.,Ltd
(Ethoxymethylene)malononitrile pictures 2022-02-22 (Ethoxymethylene)malononitrile
123-06-8
US $0.00 / KG 1KG 98.0% 100 tons Honest Joy Holdings Limited
Ethoxymethylenemalononitrile pictures 2021-07-13 Ethoxymethylenemalononitrile
123-06-8
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
ETHOXYMETHYLENEMALONITRILE ETHOXYMETHYLENEMALONONITRILE ETHOXYMETHYLENMALONONITRILE (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)- 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 ononitriL NSC 27792 α-Cyano-β-ethoxyacrylonitrile Propanedinitrile, 2-(ethoxyMethylene)- Ethoxy heartland of Methyl Malononitrile (Ethoxymethylene)malononitrile> Ethoxy malononitrile Ethoxymethylenmalononitril 2-(Ethoxymethylene)propanedinitrile (or) 2-(ethoxymethylene)malononitrile ethoxymethylmalonitrile 2-(ethoxymethylene)malonitrile 2-(ETHOXYMETHYLENE)MALONONITRILE 2-(Ethoxymethylene)propanedinitrile 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