2-(ethoxymethylidene)propanedinitrile

• ChemBase ID: 69552
• Molecular Formular: C6H6N2O
• Molecular Mass: 122.12464
• Monoisotopic Mass: 122.04801282
• SMILES: C(#N)C(=COCC)C#N
• Canonical SMILES: CCOC=C(C#N)C#N
• InChI: InChI=1S/C6H6N2O/c1-2-9-5-6(3-7)4-8/h5H,2H2,1H3
• InChIKey: OEICGMPRFOJHKO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(ethoxymethylidene)propanedinitrile
• IUPAC Traditional name: 2-(ethoxymethylidene)propanedinitrile
• Synonyms: 2-(Ethoxymethylene)propanedinitrile; (Ethoxymethylene)malonodinitrile; 1,1-Dicyano-2-ethoxyethene; 1-Ethoxy-2,2-dicyanoethene; 1-Ethoxy-2,2-dicyanoethylene; NSC 27792; α-Cyano-β-ethoxyacrylonitrile; Ethoxymethylene Malononitrile; (Ethoxymethylene)malononitrile; Ethoxymethylenemalononitrile; 2-(Ethoxymethylidene)malononitrile; Ethoxymethylenemalononitrile; (乙氧基亚甲基)丙二腈; 乙氧基亚甲基丙二腈

Database IDs

• CAS Number: 123-06-8
• EC Number: 204-597-0
• MDL Number: MFCD00001854
• Beilstein Number: 1634241
• PubChem SID: 24894622; 162035278
• PubChem CID: 67152

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.4486443
• LogD (pH = 7.4): 0.4486443
• Log P: 0.4486443
• Molar Refractivity: 32.8018 cm^3
• Polarizability: 11.947392 Å^3
• Polar Surface Area: 56.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Ethanol; Methanol
• Apperance: Off White to Pale Yellow
• Melting Point: 62-67 °C; 62-68°C; 63.5-64.5°C; 64-66 °C(lit.); 64-66°C
• Boiling Point: 160 °C/12 mmHg(lit.); 160°C; 160°C/12mm
• Flash Point: 155°C(311°F)

Safety Information

• Storage Warning: Harmful/Irritant; IRRITANT
• RTECS: OO3850000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 22-42/43; 24/25-42/43
• Safety Statements: 22-24-36/37-45; 22-36/37-45
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H317-H334; H302-H317-H334
• GHS Precautionary statements: P260-P280H-P262-P309-P310; P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥94% (NT); 95+%; 98%; TECH
• Grade: technical
• Linear Formula: C2H5OCH=C(CN)2

DETAILS

Sigma Aldrich - E6200

Caution
This product is known to be a strong sensitizing agent
Packaging
25, 100 g in poly bottle

REFERENCES

• Has also been used in the synthesis of ortho-amino benzonitrile derivatives by cyclization with active methylene compounds: Monatsh. Chem., 120, 891 (1989).
• Useful building block in the synthesis of a variety of heterocyclic molecules. For reaction with nitroacetonitrile in a high-yield synthesis of 6-amino-3-cyano-5-nitro-2-pyridone, see: Synthesis, 835 (1991). With ethyl mercaptoacetate, 3-amino-4-cyanothiophene-2-carboxylate is formed in high yield: Synthesis, 1056 (1982). With thiouronium salts, 2-alkylthio-4-amino-5-cyanopyrimidines are obtained: Helv. Chim. Acta, 81, 646 (1998).