ETHYL 2-CYANOACRYLATE

Base Information

• Chemical Name: ETHYL 2-CYANOACRYLATE
• CAS No.: 7085-85-0
• Deprecated CAS: 106717-55-9,111940-93-3,112002-50-3,122985-41-5,885041-98-5,2243906-89-8,54500-42-4,125571-49-5,66547-34-0,112002-50-3
• Molecular Formula: C6H7NO2
• Molecular Weight: 125.127
• Hs Code.: 29269090
• European Community (EC) Number: 230-391-5
• ICSC Number: 1358
• UN Number: 1993
• UNII: 2G95FOH7SF
• DSSTox Substance ID: DTXSID1025279
• Nikkaji Number: J3.726E
• Wikipedia: Ethyl_cyanoacrylate
• Wikidata: Q209366
• ChEMBL ID: CHEMBL1564920
• Mol file: 7085-85-0.mol

Synonyms:2-cyano-2-propenoic acid ethyl ester;CN4;CN2;ace-ee;Cyacrin;permabond 105;permabond 200;Krazy glue;EAC;ethyl 2-cyanoprop-2-enoate;Ethyl 2-cyanoacrylate;2-propenoic acid, 2-cyano-, ethyl ester;

Chemical Property of ETHYL 2-CYANOACRYLATE

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.427mmHg at 25°C
• Melting Point: -22 C
• Refractive Index: 1.434
• Boiling Point: 195.1 °C at 760 mmHg
• Flash Point: 79.2 °C
• PSA: 50.09000
• Density: 1.048 g/cm³
• LogP: 0.62928
• Storage Temp.: 2-8°C
• Solubility.: Acetontrle (Slightly), Benzene (Slightly), Chloroform (Slightly)
• Water Solubility.: 24μg/L at 20℃
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 125.047678466
• Heavy Atom Count: 9
• Complexity: 175

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl 2-cyanoacrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> (Meth)acrylates
• Canonical SMILES: CCOC(=O)C(=C)C#N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes and skin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: Ethyl cyanoacrylate is contained in instant glues for metal, glass, rubber, plastics, textiles, tissues and nails. It polymerizes almost instantaneously in air at room temperature and bonds immediately and strongly to surface keratin. Beauticians are exposed to contact dermatitis from nail glues.
• Uses: A cosmetic composition ECA can be used as a tissue adhesive for potential applications in cardiovascular and pulmonary surgeries. It can also be mixed with hydrophobic silica nanoparticles for the designing of cotton fabrics for medical applications. Ethyl cyanoacrylate is an acrylate compound used in instant glues to mend broken nails and to adhere glue-impregnated silk or linen to the nail plate, which is then filed to shape the nail; in medicine to glue tissues and skin cracks; to attach hair and to glue shoes, plastics, and many other materials.

Technology Process of ETHYL 2-CYANOACRYLATE

There total 11 articles about ETHYL 2-CYANOACRYLATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

formaldehyde diethyl acetal (462-95-3) + ethyl 2-cyanoacetate (105-56-6) → ethyl-2-cyanoacrilate (7085-85-0,25067-30-5)

Guidance literature:

With piperdinium acetate; at 130 ℃; for 2h; under 7500.75 Torr; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave;

Reference yield: 73.0%

ethyl 2-cyanoacetate (105-56-6) → ethyl-2-cyanoacrilate (7085-85-0,25067-30-5)

Guidance literature:

With PRIMENE 81-R iminium-MSA; at 100 ℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);

Reference yield: 70.67%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethyl 2-cyanoacetate (105-56-6) → ethyl-2-cyanoacrilate (7085-85-0,25067-30-5)

Guidance literature:

formaldehyd; ethyl 2-cyanoacetate; In acetonitrile; at 90 ℃; for 0.5h;

With ytterbium(III) triflate; In acetonitrile; Temperature; Solvent;

upstream raw materials:

formaldehyd

ethyl 2-cyanoacetate

N-methylidene-t-butylamine methanesulfonate

eschenmoser's salt

Downstream raw materials:

1-cyano-cyclohex-3-enecarboxylic acid ethyl ester

ethyl 1-(2-nitro-4-trifluoromethoxyphenyl)-5-aminopyrazol-4-carboxylate

ethyl 1-(2-nitro-3-trifluoromethylphenyl)-5-aminopyrazol-4-carboxylate

ethyl 1-(2-nitro-5-trifluoromethylphenyl)-5-aminopyrazol-4-carboxylate

Refernces

• 1、 -. "PROCESS FOR PREPARING ELECTRON DEFICIENT OLEFINS". Paragraph 0049; 0050. . Retrieved 2018/07/29.
• 2、 Radi, Marco,Vallerini, Gian Paolo,Petrelli, Alessia,Vincetti, Paolo,Costantino, Gabriele. "A one-pot two-step microwave-assisted synthesis of N1-substituted 5,6-ring-fused 2-pyridones". supporting information. p. 6905 - 6908. Retrieved 2019/04/10.