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137-05-3

Basic Information
CAS No.: 137-05-3
Name: CYANOACRYLIC ACID METHYL ESTER
Molecular Structure:
Molecular Structure of 137-05-3 (CYANOACRYLIC ACID METHYL ESTER)
Formula: C5H5 N O2
Molecular Weight: 111.1
Synonyms: Acrylicacid, 2-cyano-, methyl ester (6CI,8CI); 2-Cyanoacrylic acid methyl ester;ADhere; CA 7; CA 7 (adhesive); Cemedine 3000; Cemedine 3000 Type-II; Cemedine3000DX; Cyanobond 5000; Cyanobond SS; Eastman 910; Eastman 910 Super Glue;Fimofix P 1048; Mecrilat; Mecrilate; Mecrylate; Methyl 2-cyanoacrylate; Methylcyanoacrylate; Methyl a-cyanoacrylate; Sicomet 7000; Three Bond 1701; a-Cyanoacrylic acid methyl ester
Density: 1.08g/cm3
Melting Point: -40 °C
Boiling Point: 174.5°Cat760mmHg
Flash Point: 67.6°C
Hazard Symbols: Toxic by inhalation. TLV: TWA 2 ppm; STEL 4 ppm.
Risk Codes: 36/37/38
Safety: Moderately toxic by ingestion and inhalation routes. Experimental reproductive effects. A human eye irritant. Can bond the eyelids or skin surfaces instantly. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN.

Analytical Methods:

   

For occupational chemical analysis use OSHA: #ID-55.

PSA: 50.09000
LogP: 0.23918
Synthetic route
106647-47-6

2-acetoxy-2-cyano-propionic acid methyl ester

137-05-3

mecrilate

Conditions
ConditionsYield
With copper at 535 - 550℃; under 200 Torr; Entsteht in polymerer Form;
50-00-0

formaldehyd

105-34-0

methyl 2-cyanoacetate

137-05-3

mecrilate

Conditions
ConditionsYield
With piperidine at 80℃; Destillieren des Reaktionsprodukts bei 150grad und 1mm Druck;
With piperidine; methanol Erhitzen des Reaktionsprodukts mit Phosphor(V)-oxid, Schwefeldioxid und Hydrochinon unter vermindertem Druck;
625-56-9

Chloromethyl acetate

105-34-0

methyl 2-cyanoacetate

137-05-3

mecrilate

Conditions
ConditionsYield
With sodium methylate at 35℃; Destillieren des Reaktionsprodukts bei 150grad und 1mm Druck;
137-05-3

mecrilate

92406-83-2

(3R,5R,7R)-1-(buta-1,3-dien-2-yl)adamantane

4-Adamantan-1-yl-1-cyano-cyclohex-3-enecarboxylic acid methyl ester

Conditions
ConditionsYield
In benzene for 2h; Ambient temperature;90%
109-53-5

isobutyl vinyl ether

137-05-3

mecrilate

81245-85-4

2-isobutoxy-5-cyano-6-methoxy-3,4-dihydro-2H-pyran

Conditions
ConditionsYield
In benzene at 28℃; for 72h;87%
at 28℃; for 72h; Product distribution; Mechanism; var. temp., time, other solvent; var. electron-rich olefins;86%
In benzene at 25℃;62%
62889-07-0

trimethyl((1-(thiophen-2-yl)vinyl)oxy)silane

137-05-3

mecrilate

4-Cyano-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-4-carboxylic acid methyl ester

Conditions
ConditionsYield
In benzene at 25℃; for 3h;81%
137-05-3

mecrilate

1489-57-2

2-methylcyclohexa-1,3-diene

84959-09-1, 89104-75-6

2-cyano-2-methoxycarbonyl-5-methylbicyclo<2.2.2>oct-5-ene

Conditions
ConditionsYield
In benzene Heating;75%
In benzene Heating;
137-05-3

mecrilate

762269-61-4

5′-(4-(diphenylamino)phenyl)(2,2′-bithiophene)-5-carboxaldehyde

methyl (E)-2-cyano-3-[5'-{4-(diphenylamino)phenyl}-(2,2'-bithiophen)-5-yl]acrylate

Conditions
ConditionsYield
With piperidine In dichloromethane; acetonitrile at 20℃; for 1h; Inert atmosphere;71%
137-05-3

mecrilate

2,4-Dicyano-2-ethyl-pentanedioic acid dimethyl ester

Conditions
ConditionsYield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h;64%
119-65-3

isoquinoline

137-05-3

mecrilate

22110-53-8

1-adamantyl isocyanide

1-(adamantan-1-ylimino)-2-cyano-1,2,3,10b-tetrahydro-pyrrolo[2,1-a]isoquinoline-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In diethyl ether at 20℃; for 48h;63%
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  • Casno:

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    2-Propenoic acid,2-cyano-, methyl ester

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Chemistry

Methyl 2-cyanoacrylate(137-05-3)'s molecular formula is C9H13NO2 and its formula weight is 111.1.
The relative density of methyl 2-cyanoacrylate(137-05-3) is 1.1044(27/4°C) and it has a boiling point of  47-48°C(0.267kPa). The refractive index is about  1.443 (25 °C).
Methyl 2-cyanoacrylate(137-05-3) has the property of being dissolved in ether, chloroform, a chlorinated carbon, benzene, dioxane. It is not soluble in methanol and ethanol, and it gradually aggregated when exposed to air.
The molecular structure of methyl 2-cyanoacrylate(137-05-3):

Uses

The characteristics of methyl 2-cyanoacrylate(137-05-3) is polymerizing quickly.
Methyl 2-cyanoacrylate(137-05-3) has a strong adhesion, usually used as monomers of adhesives and polymers , also used for adhesion of the skin incision and fresh wound.

Toxicity Data With Reference

1.   

eye-hmn TD50:4 ppm

   AIHAAP    American Industrial Hygiene Association Journal. 29 (1968),558.
2.   

mmo-sat 100 µg/plate

   ENMUDM    Environmental Mutagenesis. 9 (Suppl 9)(1987),1.
3.   

mmo-sat 300 µg/plate

   MUREAV    Mutation Research. 188 (1987),97.
4.   

orl-rat LD50:1600 mg/kg

   85INA8    Documentation of the Threshold Limit Values and Biological Exposure Indices. 6 (1991),965.
5.   

ihl-rat LC50:101 ppm/6H

   85INA8    Documentation of the Threshold Limit Values and Biological Exposure Indices. 6 (1991),965.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion and inhalation routes. Experimental reproductive effects. A human eye irritant. Can bond the eyelids or skin surfaces instantly. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN.

Analytical Methods:

   

For occupational chemical analysis use OSHA: #ID-55.

Standards and Recommendations

OSHA PEL: TWA 2 ppm; STEL 4 ppm
ACGIH TLV: TWA 0.2 ppm
DFG MAK: 2 ppm (9.2 mg/m3)

Analytical Methods

For occupational chemical analysis use OSHA: #ID-55.