METHYL 2-CYANOACRYLATE supplier

Name
CYANOACRYLIC ACID METHYL ESTER
EINECS
CAS No. 137-05-3
Density 1.08g/cm³
Solubility
Melting Point -40 °C
Formula C5H5 N O2
Boiling Point 174.5°Cat760mmHg
Molecular Weight 111.1
Flash Point 67.6°C
Transport Information
Appearance
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 NO_x and CN⁻.
Analytical Methods:

For occupational chemical analysis use OSHA: #ID-55.
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Toxic by inhalation. TLV: TWA 2 ppm; STEL 4 ppm.
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
PSA 50.09000
LogP 0.23918

Synthetic route

: 106647-47-6
2-acetoxy-2-cyano-propionic acid methyl ester

: 137-05-3
mecrilate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In diethyl ether at 20℃; for 48h;	63%

...Expand

: 137-05-3
mecrilate

: 103-64-0
bromostyrene

: 81245-90-1
methyl 1-cyano-1,2-dihydronaphthalene-1-carboxylate

Conditions

Conditions	Yield
at 110℃; for 17h;	60%

: 637-69-4
4-Methoxystyrene

: 137-05-3
mecrilate

: 77321-38-1
Methyl 2-(p-Methoxyphenyl)-6-methoxy-5-cyano-3,4-dihydro-2H-pyran-4-carboxylate

Conditions

Conditions	Yield
In acetonitrile at 25℃;	51%

: 137-05-3
mecrilate

: 15185-51-0
3-oxo-3-phenyl-dithiopropionic acid

: 74598-48-4
methyl 2-(benzoylmethylene)-4-imino-1,3-dithian-5-carboxylate

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	51%

: 637-69-4
4-Methoxystyrene

: 137-05-3
mecrilate

: 81245-89-8
dimethyl 5,10-dicyano-3-methoxy-1,4,4a,5,6,7-hexahydro-1,4-ethanonaphthalene-5,10-dicarboxylate

Conditions

Conditions	Yield
In benzene at 28℃; for 24h;	50%

: 137-05-3
mecrilate

: 6476-36-4
tris(1-methylethyl)phosphine

: 183994-96-9
C14H26NO2P

Conditions

Conditions	Yield
In diethyl ether; hexane at 0℃;	48%

: 137-05-3
mecrilate

: 768-93-4
1-iodoadamantane

: 113249-57-3
Methyl 3-(1-adamantyl)-2-cyanopropanoate

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 2h; Heating;	36%

: 62889-08-1
1-(2-furyl)-1-(trimethylsilyloxy)ethylene

: 137-05-3
mecrilate

: 4-Cyano-7-oxo-4,5,6,7-tetrahydro-benzofuran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
In benzene at 25℃; for 3h;	36%

: 137-05-3
mecrilate

: ethyl 2-cyano-3,3-dimercaptoacrylate dipotassium salt

: 74598-55-3
6-Amino-2-[1-cyano-1-ethoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; water for 16h;	28%

: 137-05-3
mecrilate

: 1192-37-6
methylenecyclohexane

A: 2-Cyano-4-cyclohex-1-enyl-butyric acid methyl ester

B: 2-Methoxy-1-oxa-spiro[5.5]undec-2-ene-3-carbonitrile

C: 1-Cyano-spiro[3.5]nonane-1-carboxylic acid methyl ester

D: 1,3-Dicyano-spiro[5.5]undecane-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0 - 25℃; for 1.5h; Further byproducts given;	A 26% B 4% C 2% D 8%

...Expand

: 137-05-3
mecrilate

: 1192-37-6
methylenecyclohexane

A: 2-Cyano-4-cyclohex-1-enyl-butyric acid methyl ester

B: 2-Methoxy-1-oxa-spiro[5.5]undec-2-ene-3-carbonitrile

C: 1,3-Dicyano-spiro[5.5]undecane-1,3-dicarboxylic acid dimethyl ester

D: 2,4-Dicyano-2-(2-cyclohex-1-enyl-ethyl)-pentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0 - 25℃; for 1.5h; Further byproducts given;	A 26% B 4% C 8% D 4%

...Expand

: 513-35-9
2-methyl-but-2-ene

: 137-05-3
mecrilate

A: 2-Methoxy-5,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carbonitrile

B: 2-Cyano-4,5-dimethyl-hex-5-enoic acid methyl ester

C: 1,3-Dicyano-4,4,5-trimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

: 77257-26-2
1-cyano-2,2,3-trimethyl-cyclobutan-carbonsaeure-methylester,(13α)

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at -78 - 25℃; for 1h; Further byproducts given;	A 5% B 4% C 25% D 6%

...Expand

: 513-35-9
2-methyl-but-2-ene

: 137-05-3
mecrilate

A: 2-Methoxy-5,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carbonitrile

B: 2,4-Dicyano-2-(2,3-dimethyl-but-3-enyl)-pentanedioic acid dimethyl ester

C: 1,3-Dicyano-4,4,5-trimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

: 77257-26-2
1-cyano-2,2,3-trimethyl-cyclobutan-carbonsaeure-methylester,(13α)

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at -78 - 25℃; for 1h; Further byproducts given;	A 5% B 5% C 25% D 6%

...Expand

: 513-35-9
2-methyl-but-2-ene

: 137-05-3
mecrilate

A: 2-Methoxy-5,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carbonitrile

B: 1,3-Dicyano-4,4,5-trimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

: 77257-24-0
(1R,3S)-1-Cyano-2,2,3-trimethyl-cyclobutanecarboxylic acid methyl ester

: 77257-26-2
1-cyano-2,2,3-trimethyl-cyclobutan-carbonsaeure-methylester,(13α)

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at -78 - 25℃; for 1h; Further byproducts given;	A 5% B 25% C 3% D 6%

...Expand

: 137-05-3
mecrilate

: 119491-91-7
potassium 2-cyano-3-methoxy-3-oxoprop-1-ene-1,1-bis(thiolate)

: 74598-54-2
6-Amino-2-[1-cyano-1-methoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; water for 16h;	25%

: 112-47-0
1,10-Decanediol

: 137-05-3
mecrilate

: 60755-41-1
1,10-decanediol bis-2-cyanoacrylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In xylene for 1h; transesterification; Heating;	25%

: 137-05-3
mecrilate

: 74598-58-6
2-Cyano-3,3-dimercapto-acrylic acid isopropyl ester

: 74598-56-4
6-Amino-2-[1-cyano-1-isopropoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; water for 16h;	23%

: 592-41-6
1-hexene

: 137-05-3
mecrilate

A: (E)-2-Cyano-non-5-enoic acid methyl ester

B: 6-Butyl-2-methoxy-5,6-dihydro-4H-pyran-3-carbonitrile

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

D: 4-Butyl-1,3-dicyano-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h; Further byproducts given;	A 17% B 2% C 12% D 6%

...Expand

: 592-41-6
1-hexene

: 137-05-3
mecrilate

A: (E)-2-Cyano-non-5-enoic acid methyl ester

B: 2-Butyl-1-cyano-cyclobutanecarboxylic acid methyl ester

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

D: 4-Butyl-1,3-dicyano-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h; Further byproducts given;	A 17% B 1% C 12% D 6%

...Expand

: 592-41-6
1-hexene

: 137-05-3
mecrilate

A: (E)-2-Cyano-non-5-enoic acid methyl ester

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

C: 2,4-Dicyano-2-((E)-hept-3-enyl)-pentanedioic acid dimethyl ester

D: 4-Butyl-1,3-dicyano-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h; Further byproducts given;	A 17% B 12% C 3% D 6%

...Expand

: 922-62-3
3-Methyl-cis-2-penten

: 137-05-3
mecrilate

A: 343858-00-4
2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester

B: 345618-98-6
(E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester

C: 6-Ethyl-2-methoxy-5,6-dimethyl-5,6-dihydro-4H-pyran-3-carbonitrile

D: 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given;	A 3.6% B 3.8% C 1% D 10%

...Expand

: 922-62-3
3-Methyl-cis-2-penten

: 137-05-3
mecrilate

A: 343858-00-4
2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester

B: 345618-98-6
(E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester

C: 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

: 77257-25-1
1-cyano-2-ethyl-2,3-dimethyl-cyclobutan-carbonsaeure-methylester,(12β)

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given;	A 3.6% B 3.8% C 10% D 2.9%

...Expand

: 922-62-3
3-Methyl-cis-2-penten

: 137-05-3
mecrilate

A: 343858-00-4
2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester

B: 345618-98-6
(E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester

C: 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

: 77287-01-5
(1R,2R,3R)-1-Cyano-2-ethyl-2,3-dimethyl-cyclobutanecarboxylic acid methyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given;	A 3.6% B 3.8% C 10% D 3.4%

...Expand

: 922-62-3
3-Methyl-cis-2-penten

: 137-05-3
mecrilate

A: 345618-98-6
(E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester

B: 77257-21-7
2,4-Dicyano-2-((E)-2,3-dimethyl-pent-3-enyl)-pentanedioic acid dimethyl ester

C: 77257-23-9
2,4-Dicyano-2-(2-methyl-3-methylene-pentyl)-pentanedioic acid dimethyl ester

D: 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given. Title compound not separated from byproducts;	A 3.8% B 2% C n/a D 10%
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given. Title compound not separated from byproducts;	A 3.8% B 2% C 1% D 10%

...Expand

METHYL 2-CYANOACRYLATE Chemical Properties

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):

METHYL 2-CYANOACRYLATE 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.

METHYL 2-CYANOACRYLATE 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.

METHYL 2-CYANOACRYLATE Consensus Reports

Reported in EPA TSCA Inventory.

METHYL 2-CYANOACRYLATE 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 NO_x and CN⁻.

Analytical Methods:

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

METHYL 2-CYANOACRYLATE 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)

METHYL 2-CYANOACRYLATE Analytical Methods

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

Product Name

CYANOACRYLIC ACID METHYL ESTER

Synthetic route

METHYL 2-CYANOACRYLATE Chemical Properties

METHYL 2-CYANOACRYLATE Uses

METHYL 2-CYANOACRYLATE Toxicity Data With Reference

METHYL 2-CYANOACRYLATE Consensus Reports

METHYL 2-CYANOACRYLATE Safety Profile

METHYL 2-CYANOACRYLATE Standards and Recommendations

METHYL 2-CYANOACRYLATE Analytical Methods

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