2-(Ethoxymethylene)propanedinitrile
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Basic information
- CAS
123-06-8- Standard SMILES
CCOC=C(C#N)C#N- InChIKey
OEICGMPRFOJHKO-UHFFFAOYSA-N- Molecular formula
- C6H6N2O
- Average molar mass
- 122.12 g/mol
- Monoisotopic mass
- 122.04801281
Overview
structure given in first source
Names & identifiers
- Preferred name
- 2-(Ethoxymethylene)propanedinitrile
- IUPAC
- 2-(ethoxymethylidene)propanedinitrile
- English name
- Ethoxymethylenemalononitrile
- Molecular formula
- C6H6N2O
- Molecular weight
- 122.12
Names & synonyms
Ethoxymethylenemalononitrile123-06-8(Ethoxymethylene)malononitrilePropanedinitrile, (ethoxymethylene)-2-Cyano-3-ethoxyacrylonitrile(Ethoxymethylene)propanedinitrileMalononitrile, (ethoxymethylene)-2-(ethoxymethylene)propanedinitrile91PS2PWB1QNSC-27792DTXSID3059551ethoxymethylene-MN
Show more names
ononitriLusafkf-10NSC 27792USAF KF-10usafa-9230
RefChem:592835DTXCID2033786204-597-0ETHOXYMETHYLENEMALONITRILE2-(Ethoxymethylene)malononitrile2-(ethoxymethylidene)propanedinitrileEthoxymethylene malononitrileUSAF A-9230
Database identifiers
- CAS
123-06-8- PubChem CID
- 67152
- DTXSID
DTXSID3059551- UNII
- 91PS2PWB1Q
- EC Number
- 204-597-0
- Nikkaji
- J1.508C
Properties
Computed structural propertiesFilling in
- XLogP
- 0.5
- Topological polar surface area
- 56.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 182
Physicochemical properties
- Melting point
- 66 °C · 66 °C
- Boiling point
- 157 °C/15 · 157 °C/15 mmHg
- Density
- 1.2236 · 1.2236 (rough estimate)
- refractive index
- 1.4738 · 1.4738 (estimate)
- Flash point
- Not applicable
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMF, DMSO, Ethanol, Methanol
- form
- Solid
- color
- Clear colorless to yellow
- Water Solubility
- insoluble
- BRN
- 1634241 · 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 · 123-06-8(CAS DataBase Reference)
- EWG's Food Scores
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (23.2%): Toxic if swallowed [Danger Acute toxicity, oral]
P233, P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P316, P321, P330, P333+P317, P342+P316, P361+P364, P362+P364, P403, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 56 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (23.2%)
Safety data
- F
- 21
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- OO3850000
- ridadr
- 3439
- hs_code
- 2926909090
- Toxicity
- mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689,
- risk_code
- 22-42/43-23/24/25-43-20/21/22-R42/43-R23/24/25-R22
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn,T,Xi
- safety_code
- 22-36/37-45-36/37/39-26-36-24/25-S45-S36/37/39-S26-S22
- hazard_class
- 6.1
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationPropanedinitrile, 2-(ethoxymethylene)-: ACTIVE
Applications
DescriptionEthoxymethylenemalononitrile (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.
UsesChemical intermediate.
UsesEthoxymethylene Malononitrile (cas# 123-06-8) is a compound useful in organic synthesis.
Preparation methods
PreparationTriethyl 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
129 records
Compound notes
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