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Ethyl cyanoacrylate

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Name

Ethyl cyanoacrylate

EINECS 230-391-5
CAS No. 7085-85-0 Density 1.048 g/cm3
PSA 50.09000 LogP 0.62928
Solubility soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride Melting Point -22 C
Formula C6H7NO2 Boiling Point 195.1 °C at 760 mmHg
Molecular Weight 125.127 Flash Point 79.2 °C
Transport Information N/A Appearance colorless liquid
Safety 22-24/25-26-23 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 7085-85-0 (ETHYL 2-CYANOACRYLATE) Hazard Symbols IrritantXi
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;

Article Data 21

Ethyl cyanoacrylate Synthetic route

462-95-3

formaldehyde diethyl acetal

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
With piperdinium acetate at 130℃; under 7500.75 Torr; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave;80%
105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
With PRIMENE 81-R iminium-MSA at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);73%
50-00-0

formaldehyd

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
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
13987-61-6

N-methylene-tert-butylamine

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
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

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);23%
1022085-81-9

N-methylidene-t-butylamine methanesulfonate

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
In chloroform at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent);~ 70 %Spectr.
33797-51-2

eschenmoser's salt

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
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-)

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
In chloroform-d1 at 20 - 70℃; for 3h; Product distribution / selectivity;64 %Spectr.
1346549-53-8

N-methyl-N-(2-aldimino-2-methyl-propyl)-pyrrolidinium bis(trifluoromethylsulfonimide)

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

Conditions
ConditionsYield
at 150℃; under 0.525053 Torr;
1448709-78-1

C5H12N(1+)*C2H3O2(1-)

105-56-6

ethyl 2-cyanoacetate

7085-85-0

ethyl 2-cyanoacrylate

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

Ethyl cyanoacrylate Consensus Reports

Reported in EPA TSCA Inventory.

Ethyl cyanoacrylate Standards and Recommendations

ACGIH TLV: TWA 0.2 ppm

Ethyl cyanoacrylate Specification

The Ethyl cyanoacrylate, with the CAS registry number 7085-85-0 and EINECS registry number 230-391-5, has the systematic name of ethyl 2-cyanoprop-2-enoate. It is a kind of clear colourless liquid, and belongs to the following product categories: Organics; All Aliphatics; Aliphatics; Intermediates & Fine Chemicals; Pharmaceuticals; AcrylonitrileCarbonyl Compounds; Acrylic Monomers; C6 to C7; Esters; Monomers. And the molecular formula of this chemical is C6H7NO2. What's more, it should be stored at 2-8°C.

The Ethyl cyanoacrylate is also known as EAC. It is a cyanoacrylate ester, and soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. It is the main component of cyanoacrylate glues, and super glue and Krazy glue are believed to be virtually 100% ECA. What's more, it will polymerize rapidly in the presence of moisture.

The physical properties of Ethyl cyanoacrylate are as following: (1)ACD/LogP: 0.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.23; (4)ACD/LogD (pH 7.4): 0.23; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 31.63; (8)ACD/KOC (pH 7.4): 31.63; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 50.09 Å2; (13)Index of Refraction: 1.434; (14)Molar Refractivity: 31.1 cm3; (15)Molar Volume: 119.3 cm3; (16)Polarizability: 12.33×10-24cm3; (17)Surface Tension: 34.4 dyne/cm; (18)Density: 1.048 g/cm3; (19)Flash Point: 79.2 °C; (20)Enthalpy of Vaporization: 43.13 kJ/mol; (21)Boiling Point: 195.1 °C at 760 mmHg; (22)Vapour Pressure: 0.427 mmHg at 25°C.

Preparation of Ethyl cyanoacrylate: It can be prepared by the condensation of formaldehyde with ethyl cyanoacetate. The reaction equation is as follows:
CH2(CN)CO2Et + CH2O → CH2=C(CN)CO2Et + H2O

Uses of Ethyl cyanoacrylate: It is used for gluing of various materials. Its applications is also in medicine, for liquid bandages and for suture-less surgery, but it is used less often than the less toxic n-butyl and octyl cyanoacrylates.

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Do not breathe dust and then try to avoid contacting with skin and eyes. Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer); In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: N#C/C(=C)C(=O)OCC
(2)InChI: InChI=1/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3
(3)InChIKey: FGBJXOREULPLGL-UHFFFAOYAG

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 5mL/kg (5mL/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
International Journal of Toxicology. Vol. 16(Suppl,

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