2-(Ethoxymethylene)propanedinitrile (HCID 67152)

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 properties

XLogP: 0.5
Topological polar surface area: 56.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 9
Formal charge: 0
Complexity: 182

Physicochemical properties

Melting point: 64 · 64-66 °C(lit.)
Boiling point: 160 °C12 · 160 °C12 mm Hg(lit.)
Density: 1.2236 · 1.2236 (rough estimate)
refractive index: 1.4738 · 1.4738 (estimate)
Flash point: 155 °C · 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 · 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: 1 · 1
FDA UNII: 91 PS2PWB1Q · 91PS2PWB1Q
NIST Chemistry Reference: Propanedinitrile, (ethoxymethylene)-(123-06-8)
EPA Substance Registry System: Propanedinitrile, (ethoxymethylene)- (123-06-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 302 · H302-H317-H334
Precautionary statements: 280 · P280-P301+P312+P330-P302+P352
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes: Xn,T,Xi
Risk Statements: 22 · 22-42/43-23/24/25-43-20/21/22-R42/43-R23/24/25-R22
Safety Statements: 22 · 22-36/37-45-36/37/39-26-36-24/25-S45-S36/37/39-S26-S22
RIDADR: 3439 · 3439
WGK Germany: 3 · 3
RTECS: 3850000 · OO3850000
F: 21 · 21
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29269090 · 29269090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralResp · Acute Tox. 4 OralResp. Sens. 1Skin Sens. 1
Toxicity: 50 · mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689,

Safety & regulation

GHS classification

GHS Classification · 4 items

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: 29269090
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
Storage Class: 11 - Combustible Solids
packing_group: III
Hazard statements: H302-H317-H334
Hazard Classifications: Acute Tox. 4 OralResp. Sens. 1Skin Sens. 1
Precautionary statements: P280-P301+P312+P330-P302+P352

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPropanedinitrile, 2-(ethoxymethylene)-: ACTIVE

Applications · 3 items

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 · 1 item

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.