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| CAS No.: | 7085-85-0 |
|---|---|
| Name: | ETHYL 2-CYANOACRYLATE |
| Molecular Structure: | |
|
|
|
| Formula: | C6H7NO2 |
| Molecular Weight: | 125.127 |
| 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; |
| EINECS: | 230-391-5 |
| Density: | 1.048 g/cm3 |
| Melting Point: | -22 C |
| Boiling Point: | 195.1 °C at 760 mmHg |
| Flash Point: | 79.2 °C |
| Solubility: | soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride |
| Appearance: | colorless liquid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 22-24/25-26-23 |
| PSA: | 50.09000 |
| LogP: | 0.62928 |
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| Conditions | Yield |
|---|---|
| With piperdinium acetate at 130℃; under 7500.75 Torr; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave; | 80% |
| Conditions | Yield |
|---|---|
| With PRIMENE 81-R iminium-MSA at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent); | 73% |
| 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 |
| 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. |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| In chloroform at 100℃; for 0.0166667h; Product distribution / selectivity; Neat (no solvent); | ~ 70 %Spectr. |
| 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; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| at 150℃; under 0.525053 Torr; |
| Conditions | Yield |
|---|---|
| In acetonitrile at 20 - 25℃; Acidic conditions; |
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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, |