7085-85-0

Basic information

• Product Name: ETHYL 2-CYANOACRYLATE
• Synonyms: 2-cyano-2-propenoicaciethylester;2-cyanoacrylicacidethylester;2-cyano-acrylicaciethylester;2-propenoic,2-cyano-,ethylester;2-Propenoicacid,2-cyano-,ethylester;910em;ace-e50;ace-ee
• CAS NO: 7085-85-0
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.13
• EINECS: 230-391-5
• Product Categories: Organics;All Aliphatics;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals;AcrylonitrileCarbonyl Compounds;Acrylic Monomers;C6 to C7;Esters;Monomers
• Mol File: 7085-85-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: -20 to -25°
• Boiling Point: bp 54-56° (0.21-0.40 kPa)
• Flash Point: 85 °C
• Appearance: Clear colorless to slightly yellow/liquid
• Density: 1.04
• Vapor Pressure: 0.427mmHg at 25°C
• Refractive Index: nD20 1.4391
• Storage Temp.: 2-8°C
• Solubility: Acetontrle (Slightly), Benzene (Slightly), Chloroform (Slightly)
• Water Solubility: 24μg/L at 20℃
• Stability: Unstable - polymerizes rapidly, especially in the presence of moisture. Combustible. Incompatible with strong oxidizing agents,
• CAS DataBase Reference: ETHYL 2-CYANOACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CYANOACRYLATE(7085-85-0)
• EPA Substance Registry System: ETHYL 2-CYANOACRYLATE(7085-85-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26-23
• WGK Germany: 1
• RTECS: UD3330000
• Hazardous Substances Data: 7085-85-0(Hazardous Substances Data)

Usage

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.

Chemical Properties

Clear Colourless Liquid

Uses

Different sources of media describe the Uses of 7085-85-0 differently. You can refer to the following data:
1. A cosmetic composition
2. 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.
3. 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.

General Description

Ethyl 2-cyanoacrylate (ECA) is a monomeric adhesive that can be used on a variety of materials such as metals, plastics, rubber, ceramics, and wood. It forms a one part adhesive system that can also be used as a primer.

Hazard

An inhalation hazard.

Flammability and Explosibility

Notclassified

Safety Profile

An inhalation hazard. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3

Synthetic route

formaldehyde diethyl acetal (462-95-3) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
With piperdinium acetate at 130℃; under 7500.75 Torr; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave;	80%

ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
With PRIMENE 81-R iminium-MSA at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);	73%

formaldehyd (50-00-0) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
Stage #1: formaldehyd; ethyl 2-cyanoacetate In acetonitrile at 90℃; for 0.5h; Stage #2: With ytterbium(III) triflate In acetonitrile Temperature; Solvent;	70.67%
With triethylamine In ethanol
With pyridine

N-methylene-tert-butylamine (13987-61-6) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
Stage #1: N-methylene-tert-butylamine With methanesulfonic acid; sulfuric acid In chloroform-d1 at 0℃; Stage #2: ethyl 2-cyanoacetate In chloroform-d1 at 20 - 70℃; Product distribution / selectivity;	64%
With methanesulfonic acid; sulfuric acid In chloroform-d1 at 0 - 70℃; for 4.5h; Product distribution / selectivity; screw-capped test-tube;	~ 70 - ~ 85 %Spectr.

PRIMENE MD diimine methanesulfonate + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);	23%

N-methylidene-t-butylamine methanesulfonate (1022085-81-9) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
In chloroform at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);	~ 70 %Spectr.

eschenmoser's salt (33797-51-2) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
With methanesulfonic acid; sulfuric acid In chloroform-d1 at 20 - 70℃; for 3h; Product distribution / selectivity; screw-capped test-tube;
Stage #1: eschenmoser's salt With methanesulfonic acid; sulfuric acid In chloroform-d1 Stage #2: ethyl 2-cyanoacetate In chloroform-d1 at 70℃; for 3h; Product distribution / selectivity;

CH3O3S(1-)*3C5H12N(1+)*HO4S(1-)*0.5O4S(2-) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
In chloroform-d1 at 20 - 70℃; for 3h; Product distribution / selectivity;	64 %Spectr.

N-methyl-N-(2-aldimino-2-methyl-propyl)-pyrrolidinium bis(trifluoromethylsulfonimide) (1346549-53-8) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
at 150℃; under 0.525053 Torr;

C5H12N(1+)*C2H3O2(1-) (1448709-78-1) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacrylate (7085-85-0)

Conditions	Yield
In acetonitrile at 20 - 25℃; Acidic conditions;

ethyl 2-cyanoacrylate (7085-85-0) + diethyl-phospholan-1-yl-amine (52054-23-6) → 2-diethylamino(tetramethylene)-phosphonio-1-cyano-1-ethoxycarbonylethanide

Conditions	Yield
In benzene at 20℃; for 3h;	99%
In benzene Yield given;

tris-n-propylphosphine (2234-97-1) + ethyl 2-cyanoacrylate (7085-85-0) → 2-tripropylphosphonio-1-cyano-1-ethoxycarbonylethanide (154927-65-8)

Conditions	Yield
In benzene at 20℃; for 3h;	97%
In benzene Yield given;

ethyl 2-cyanoacrylate (7085-85-0) + 2-mercaptoethylamine hydrochloride (156-57-0) → ethyl 3-(2-aminoethylthio)-2-cyanopropionate hydrochloride (139223-61-3)

Conditions	Yield
In acetic acid for 2h;	97%

tributylphosphine (998-40-3) + ethyl 2-cyanoacrylate (7085-85-0) → 2-tributylphosphonio-1-cyano-1-ethoxycarbonylethanide (154927-66-9)

Conditions	Yield
In benzene at 20℃; for 3h;	96%
In benzene Yield given;

ethyl 2-cyanoacrylate (7085-85-0) + DL-cysteine hydrochloride (10318-18-0) → ethyl 3-(β-amino-β-carboxyethylthio)-2-cyanopropionate hydrochloride (68219-46-5)

Conditions	Yield
In acetic acid for 2h;	95%

ethyl 2-cyanoacrylate (7085-85-0) + C12H30N3P → 2-(tert-butylamino)bis(diethylamino)phosphonio-1-cyano-1-ethoxycarbonylethanide

Conditions	Yield
In benzene at 20℃; for 3h;	95%
In benzene Yield given;

ethyl 2-cyanoacrylate (7085-85-0) + mercaptoacetic acid (68-11-1) → ethyl 3-(carboxymethylthio)-2-cyanopropionate (139022-55-2)

Conditions	Yield
In acetone for 2h;	95%

ethyl 2-cyanoacrylate (7085-85-0) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → ethyl 1-benzyl-3-cyanopyrrolidine-3-carboxylate (1312815-01-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere;	94%
With trifluoroacetic acid In dichloromethane at 0 - 20℃;	94%
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16h;	2.4 g

ethyl 2-cyanoacrylate (7085-85-0) + ortho-cresidine (16452-01-0) → 2-cyano-3-(3-methoxy-4-methylphenyl)aminoacrylic acid ethyl ester (1204472-64-9)

Conditions	Yield
In toluene for 5h; Michael Addition; Reflux;	94%

ethyl 2-cyanoacrylate (7085-85-0) + benzo[1,3,2]dioxaphosphol-2-yl-tert-butyl-amine (51439-14-6) → C16H21N2O4P

Conditions	Yield
In benzene	91%

methyl 2-nitroacetate (2483-57-0) + ethyl 2-cyanoacrylate (7085-85-0) → 2-nitro-4-cyano-1,5-pentanedioic acid 1-methyl ester 5-ethyl ester

Conditions	Yield
With piperidine In acetonitrile at 20℃; for 24h; Mechanism; other CH-acids;	90%
With piperidine In acetonitrile at 20℃; for 14h;	90%

ethyl 2-cyanoacrylate (7085-85-0) + ethane-1,2-dithiol (540-63-6) → 2-Cyano-3-[2-(2-cyano-2-ethoxycarbonyl-ethylsulfanyl)-ethylsulfanyl]-propionic acid ethyl ester (139022-56-3)

Conditions	Yield
In acetone for 3h;	90%

ethyl 2-cyanoacrylate (7085-85-0) + hexaethylphosphoric triamide (2283-11-6) → 2-hexaethyltriaminophosphonio-1-cyano-1-ethoxycarbonylethanide (154927-67-0)

Conditions	Yield
In benzene at 20℃; for 3h;	87%
In benzene Yield given;

sodium cyanide (773837-37-9) + ethyl 2-cyanoacrylate (7085-85-0) → ethyl 2,3-dicyanopropanoate (40497-11-8)

Conditions	Yield
Stage #1: sodium cyanide In isopropyl alcohol at 30℃; for 4h; Stage #2: ethyl-2-cyanoacrilate With methanesulfonic acid In isopropyl alcohol at 20 - 25℃; for 6h; Solvent; Reagent/catalyst; Temperature;	86%
Stage #1: sodium cyanide; ethyl-2-cyanoacrilate With methanesulfonic acid In isopropyl alcohol at 20 - 25℃; for 6h; Stage #2: With hydrogenchloride In isopropyl alcohol at 10℃; Product distribution / selectivity;

ethyl 2-cyanoacrylate (7085-85-0) → ethyl 2-cyanopropionate (1572-99-2)

Conditions	Yield
With trifluoroacetic acid at 0℃;	85%
With trifluoroacetic acid at 0℃; Mechanism;	85%
With hydrogen; hydrotalcite-supported palladium nanoparticles; palladium In toluene at 60℃; under 760 Torr; for 1h;

2-(2'-hydroxyethoxy)-1,3,2-dioxaphospholane (1073-75-2) + ethyl 2-cyanoacrylate (7085-85-0) → 2-Cyano-3-(1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]non-5-yl)-propionic acid ethyl ester

Conditions	Yield
In benzene	83%

ethyl 2-cyanoacrylate (7085-85-0) → diethyl 3,3'-thiobis(2-cyanopropionate) (139022-60-9)

Conditions	Yield
With hydrogen sulfide; triethylamine In benzene at 20℃; for 3h;	80%

isoindole-1,3-diylidenediamine (160956-25-2, 160956-26-3, 160956-27-4, 160956-28-5, 160956-29-6) + ethyl 2-cyanoacrylate (7085-85-0) → 2,2′-(1H-isoindole-1,3(2H)-diylidene)-bis-(cyanoacetic acid ethyl ester)

Conditions	Yield
With acetic acid Reflux;	79%

ethyl 2-cyanoacrylate (7085-85-0) + ethyl 5‑amino‑3‑(methylthio)‑1H‑pyrazole‑4‑carboxylate (54417-51-5) → ethyl 6-cyano-5-hydroxy-6,7-dihydro-2-methylthiopyrazolo[1,5-a]pyrimidine-3-carboxylate

Conditions	Yield
With pyridine Heating;	77%

ethyl 2-cyanoacrylate (7085-85-0) + 4-amino-2-methyl-5,6,11-trioxo-1,4,4a,5,6,11,12,12a-octahydro-1,12-diaza-naphthacene-3-carbonitrile (497833-38-2) → 1,6-diamino-5-cyano-7,8,13-trioxo-4,6,6a,7,8,13,14,14a-octahydro-3H-14,14b-diaza-benzo[a]naphthacene-2-carboxylic acid ethyl ester

Conditions	Yield
With pyridine Heating;	75%

ethyl 2-cyanoacrylate (7085-85-0) + 2-acetyl-4-methylanisole (20628-07-3) → (E)-2-Cyano-3-(2-methoxy-5-methyl-phenyl)-but-2-enoic acid ethyl ester (58848-52-5)

Conditions	Yield
With ammonium acetate; acetic acid In benzene Heating;	75%

ethyl 2-cyanoacrylate (7085-85-0) + 1-(2,5-Dimethoxy-4-methyl-phenyl)-ethanone (13720-58-6) → (E)-2-Cyano-3-(2,5-dimethoxy-4-methyl-phenyl)-but-2-enoic acid ethyl ester (518014-04-5)

Conditions	Yield
With ammonium acetate; acetic acid In benzene Heating;	75%

ethyl 2-cyanoacrylate (7085-85-0) + dipyrocatecholmonophosphite (57559-06-5) → C18H16NO6P

Conditions	Yield
In benzene	74%

ethyl 2-cyanoacrylate (7085-85-0) + 2-methylpropan-2-thiol (75-66-1) → 3-tert-Butylsulfanyl-2-cyano-propionic acid ethyl ester (133586-58-0)

Conditions	Yield
In benzene at 20℃; for 24h;	74%

ethyl 2-cyanoacrylate (7085-85-0) + 4-methoxy-3-methylacetophenone (10024-90-5) → (E)-2-Cyano-3-(4-methoxy-3-methyl-phenyl)-but-2-enoic acid ethyl ester (64597-54-2)

Conditions	Yield
With ammonium acetate; acetic acid In benzene Heating;	73%

ethyl 2-cyanoacrylate (7085-85-0) + Benzo[1,3,2]dioxaphosphol-2-yl-cyclohexyl-amine → C18H23N2O4P

Conditions	Yield
In benzene	72%

ethyl 2-cyanoacrylate (7085-85-0) + 3-fluoro-4-bromophenylamine (656-65-5) → ethyl 3-[(4-bromo-3-fluorophenyl)amino]-2-cyanoprop-2-enoate

Conditions	Yield
In ethanol at 80℃; for 5h; Inert atmosphere;	72%

ethyl 2-cyanoacrylate (7085-85-0) + 2,4-dimethyl-benzoic acid (611-01-8) → 2-cyano-5,7-dimethyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylic acid ethyl ester

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In 1,2-dichloro-ethane at 140℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	72%

Upstream product

• 462-95-3 formaldehyde diethyl acetal 
• 105-56-6 ethyl 2-cyanoacetate 
• 1448709-78-1 C₅H₁₂N⁽¹⁺⁾*C₂H₃O₂^(1-) 
• 1346549-53-8 N-methyl-N-(2-aldimino-2-methyl-propyl)-pyrrolidinium bis(trifluoromethylsulfonimide) 
• 13987-61-6 N-methylene-tert-butylamine 
• 33797-51-2 eschenmoser's salt 
• 1022085-81-9 N-methylidene-t-butylamine methanesulfonate 
• 50-00-0 formaldehyd 

Downstream Products

• 1045770-57-7 C₁₈H₁₈N₂O₅ 
• 1045770-55-5 C₂₀H₂₁NO₃ 
• 1045770-81-7 C₂₄H₂₅NO₄ 
• 1045770-79-3 C₂₄H₂₅NO₄ 
• 1045770-45-3 (1S,2R,5R)-1 cyano-3-formyl-5-methyl-2-phenyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 1045770-47-5 (1R,2R,5R)-1 cyano-3-formyl-5-methyl-2-phenyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 1045770-59-9 C₁₃H₁₇NO₃ 
• 1045770-53-3 C₁₉H₂₁NO₃ 
• 1253427-91-6 ethyl 1-(2-nitro-4-trifluoromethoxyphenyl)-5-aminopyrazol-4-carboxylate 
• 1253427-77-8 ethyl 1-(2-nitro-3-trifluoromethylphenyl)-5-aminopyrazol-4-carboxylate 
• 1253427-82-5 ethyl 1-(2-nitro-5-trifluoromethylphenyl)-5-aminopyrazol-4-carboxylate 
• 27058-47-5 Ethyl 3 benzamidino-2 cyanoacrylate 
• 6606-65-1 n-butyl cyanoacrylate 
• 1312815-02-3 methyl 3-(aminomethyl)-1-benzylpyrrolidine-3-carboxylate 

Relevant articles and documents

Preparation method of alpha-cyanoacrylate

The invention relates to a preparation method of alpha-cyanoacrylate. The preparation method mainly includes the following steps that methyl cyanoacetate or ethyl cyanoacetate and formaldehyde are subjected to a condensation reaction to obtain a cyanoacrylate prepolymer; the cyanoacrylate prepolymer is cracked and rectified to obtain a methyl cyanoacrylate monomer or an ethyl cyanoacrylate monomer; and an anionic polymerization inhibitor, a free radical polymerization inhibitor, a catalyst and alcohol are added to the methyl cyanoacrylate monomer or the ethyl cyanoacrylate monomer for an esterexchange reaction, and the alpha-cyanoacrylate is obtained. According to the preparation method of the alpha-cyanoacrylate, the long-chain alpha-cyanoacrylate with the high content can be directly prepared, the depolymerization process under high-temperature and high-vacuum conditions is not required, the cost is lowered, the yield of products is increased, and the purity and stability of the products are improved.

Method for synthesizing cyanoacrylate

The invention discloses a method for synthesizing cyanoacrylate. The method comprises steps as follows: cyanoacetic ester and dialkoxymethane are taken as raw materials and have a condensation reaction under the catalytic action of a catalyst, and a reaction mixture of a cyanoacrylate containing oligomer and byproduct alcohol is obtained; the byproduct alcohol and unreacted dialkoxymethane are separated, a stabilizer is added to the remaining reaction mixture, cracking distillation under the reduced pressure is performed, and a cyanoacrylate crude product is obtained; the crude product is purified, and a finished product, namely, cyanoacrylate is obtained. Solid paraformaldehyde is not used any more, the difficulty of solid feeding is reduced, a dehydration step is not required, a dehydrating agent is not required to be used, defects of a condensation polymerization process using solid paraformaldehyde and using a solvent for continuous dehydration in conventional cyanoacrylate synthesis are avoided, the reaction process is easier to control, the process is simple, the operability is high, the method is economical and reasonable, discharge of three wastes and pollution to the environment are greatly reduced, and the method has good social benefits.

1,1-DISUBSTITUTED ETHYLENE PROCESS

New and improved processes for the production of 1,1-disubstituted ethylenes.